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My Life-Changing Island Hopping Cruise Adventure in the Western Caribbean

Island Hopping Cruise Adventures Offer an Unforgettable Experience

Make A Jamaica Trip Full With Friendship

W hen I first set foot in Jamaica, I was greeted by the island's relaxing energy and warming sun. I had spent a few months in a cold region before heading to the Caribbean for my island hopping cruise adventure, and I longed for healing time in paradise. The Caribbean is packed with postcard islands, so standing out from that crowd is no easy task, but Jamaica is something else. It lulls you with its easygoing music, friendly locals, spirited street life, and succulent island cuisine. Jamaica is a place you can see, hear and taste — it is simply beaming with life.

Under The Sea In Belize With Ease

Grand Cayman’s Grand Expectations For Generations

Only three words mattered to me when our cruise ship anchored in Grand Cayman ; Seven. Mile. Beach. I had heard of this crescent-shaped, award-winning slice of beach paradise many times throughout the years, with its wonderfully soft sand and impossibly clear waters, and I was desperate to reach it. I could see the sparkling water from the cab and the closer I got, the more beauty I could see. Then, finally, I was walking on the powdery sand and soon broke into a sprint toward the water. Seven Mile Beach is an expansive waterfront open to the public, and it's lined by luxury resorts, restaurants, and bars. You can parasail, kayak, paddle-board or just chill on a hammock. I chose the latter.

After taking in the beauty of Seven Mile Beach, I took a tour to what locals call the Sister Islands (Cayman Brac and Little Cayman) to try something I had never done before: bird-watching. The islands feature more than 200 bird species and are home to more iguanas than humans. Locals were incredibly friendly and helped me find the best spots to watch wildlife. It was a refreshing experience during which I could slow down and admire the magic of the Cayman Islands.

Roatán’s Beauty, Never Miss The Offshore Bliss

When first visiting Roatán in Honduras , I just wanted to go diving, but then I realized that a lot of Roatán's beauty lies above the water as well. Trying to leave "the best for last," I opted for skipping the splash and headed to the Monkey Trail Canopy for some zip-lining. I was flying high above the ground and then through the forest, watching monkeys and macaws go about their lives. Then, suddenly, I saw a sloth hanging from a tree branch. A local woman told me that sloths symbolize relaxation, groundedness, and patience. Being in the presence of such a revered animal was enlightening and soothing, as I always say I want to live slow, like the majestic sloth.

After my jungle exploration, it was time to enjoy what Roatán does best: scuba diving. The island is lined by a surprising amount of coral reef, where brightly colored tropical fish calmly swim against a turquoise background. I felt like a mermaid as I traversed among the underwater beauty, becoming one with the surroundings. Port Royal and Mary's Place are some of the best spots for snorkeling or diving. I was able to easily find coral gardens, and the famous Odyssey and Aguila shipwrecks. My pictures from this part of the trip were some of the best I have ever taken, really capturing a world very few people get to see in person.

Propel To Cozumel, La Isla Bonita

Cozumel is what Caribbean island hopping dreams are made of — it's quiet and playful, busy and isolated, historic and modern. Cozumel is beautiful. Located in the Yucatán Peninsula of Mexico, Cozumel welcomed me with open arms as I explored its coast and beyond. I rented a scooter and zipped around at my own pace, making stops to discover hidden beaches, Maya ruins and off-road trails. I circled the entire island in less than two hours. By far my favorite beach was Palancar because of the great snorkeling.

I also made a quick stop by Punta Sur Eco-Park, the largest ecological reserve on the island of Cozumel. Mangrove swamps and tropical jungles were filled with wild flamingos flying over the lagoon, fish gliding under the water, and iguanas running aground. I went up to the top of a lighthouse and was welcomed by sweeping views of the Caribbean Sea. I took a deep breath to inhale the healing salty air and knew right then and there that my trip had been worth every effort.

Another great stop was the Maya ruins in San Gervasio, the center of pilgrimages where the Maya worshiped "Ixchel," the goddess of medicine. I arrived in the middle of a tropical jungle to find several structures spread out through the area. After some time sauntering around the sacred paths, known to the ancient Maya as Sacbe, I noticed a big hole in the ground. I asked a local about it, and he said it was a portal to the Netherworld. I slowly got closer to the hole, which was surrounded by rocks and saw a body of water inside. "Or maybe it's just a tiny cenote," he then said, smiling. A small cenote is a source of water, but according to Maya mythology, it's a passage to a realm known as Xibalba or the "place of fright." The holes were supposed to be ruled by death gods and their helpers. I stared at the mystical sinkhole and could hear the water running. After a while, it started to sound like a beautiful song. It's not just a cenote, I thought.

After driving around the island, I decided to close my visit to Cozumel with a chocolate margarita from the Mayan Cacao Company. Roberto, my tour guide, said we were embarking on an interactive experience. "This is not a museum," he said, "you are part of the action." And he was right. I was not just learning about cacao and its importance to the Maya — they called it the "food of the gods" — but I actively participated in the tour. I was part of a Maya purification ritual, made my own chocolate using historical utensils, and concocted a chocolate margarita using local tequila. In the end, I learned that chocolate was not just a delicious treat but a precious and valuable currency to the Maya.

Taking A Western Caribbean Island Vacation Can Change Your Life

Written By MELISSA ALVARADO SIERRA

Melissa Alvarado Sierra is a journalist, author and sailor. She's been exploring coastal destinations around the world for more than a decade, always searching for authentic experiences to share with her adventurous readers. Her work has been published or is forthcoming in The New York Times, Lonely Planet, Orion Magazine, AFAR, USA Today and others.

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The Ultimate Guide to Caribbean Island-Hopping

See recent posts by Lilly Graves

Ever dream of visiting multiple islands in the Caribbean on the same vacation, without sharing space with hundreds (er, thousands) of cruisers who are on the same ship and trip? You’re off to a good start. The close proximity of the Caribbean islands makes it the perfect base for a freedom-filled island-hopping adventure with various activities, cultures, and island vibes to choose from. From golden sandy beaches and water sports to barefoot restaurants and rum shops, this famously laid-back Caribbean lifestyle is ideal for a tailor-made trip—and there are several itineraries ranging from budget-friendly to splurge-worthy. Below we’ve listed four Caribbean island-hopping itinerary ideas, along with some tips and tricks. 

Caribbean Island-Hopping Itinerary #1: Use Public Ferries

Though not technically part of the Caribbean (it’s actually part of the North Atlantic), the Bahamas exudes everything you think of when dreaming of a Caribbean vacation. The island group is comprised of more than 700 stunning subtropical islands as well as thousands of cays. Of course, having your own boat or prop plane to explore the Bahamas is the best-case scenario, but if you’re not part of the one percent, we’ll give you a transportation option that is easy-peasy and won’t break the bank: the public ferry.

Nassau: Begin your adventure in the country’s capital, Nassau, 184 miles from Miami. This bustling capital city hub provides a nice mix of city and island life, as well as Bahamian culture and lifestyle. You can either stay a night or two on this island (New Providence) or head to neighboring Paradise Island—home of the Atlantis mega-resort and its gigantic waterpark, as well as a handful of other properties. If you don’t stay on Paradise Island, make sure to head across the bridge, which charges a nominal fee, and spend some time on Cabbage Beach. This is one of the world’s most famous stretches of sand for a reason.

Harbour Island: Now that you’ve seen two of the country’s more popular islands, next, take a morning ferry from Nassau to Harbour Island, via BahamasFerries.com, where you’ll find small island charm and long stretches of soft pink sand. There are some wonderful boutique hotels here that offer easy access to the beach. You can also spend time wandering through the quiet streets looking for pastel-hued cottages and unique architecture with nothing more than the occasional chicken and golf cart in your path.

Eleuthera: Since Harbour Island is located just off a much bigger island—Eleuthera—you can head there next, by water taxi (a short and cheap ride) to finish the trip in the pineapple capital of the world. Locals say that the Gregory Town pineapple claims to be the sweetest on the planet, and it is believed that the Bahamas was the first country to produce the fruit. While here, visit the Glass Window Bridge—a thin pathway connecting the rough Atlantic Ocean and the calm waters of the Bight of Eleuthera for striking photo ops. From here, take the ferry back to Nassau.

Exuma: You can finish the trip in Nassau (that’s four key islands) or continue the journey (optional) through more remote areas of the Bahamas. For instance, take another ferry from Nassau to Georgetown (Exuma Island), or jump on a 40-minute commercial flight to Great Exuma, via Bahamasair . Either way, the Exumas consists of 365 islands and is known for swimming pigs, nurse sharks, colorful fish, coral reefs, and other marine life, as well as boating excursions, on-island tours, and miles of rarely-visited beaches—in other words, plenty of Caribbean activities to keep you busy for days.

Our Bahamas Hotel Pick : The Cove at Atlantis

Caribbean Island-Hopping Itinerary #3: Book Through a Tour Operator

For the easiest island-hopping itinerary, book through a tour operator. Sure, this alleviates some of the adventure factors of planning your own trip, but you’ll still be on your very own multi-island vacation without the cruise ship crowds. Check out companies like Abercrombie & Kent, G Adventures , or the U.K.-based company Tropic Breeze for various sailing excursions and options.

One affordable G Adventures sailing trip ($1699 at the time of publishing) buys an unforgettable eight-night trip sailing around St. Lucia and St. Vincent and the Grenadines. Since resorts are generally so expensive year-round, sleeping on a catamaran keeps costs low AND allows easy access to hidden coves, isolated beaches, and snorkeling sites. Oh, and the cook makes fresh Creole cuisine for a taste of island life every night. Yum.

Our St. Lucia Hotel Pick: Sugar Beach, A Vicer oy Resort

Caribbean Island-Hopping Itinerary #3: Plan your Own One-Way Adventure

So you consider yourself a savvy trip planner and want to create your own Caribbean island-hopping itinerary? That can be tricky. Finding direct flights between Caribbean islands can either be difficult, expensive—or both, but there are options. This sample itinerary allows you to see four French Caribbean islands, accessed with affordable, direct, one-way flights—in one fell swoop.

St. Martin: You’ll arrive first at St. Martin, an island divided between the French Republic and the Kingdom of the Netherlands. We recommend staying on the French side due to its romantic restaurants, charming boutiques, and sandy beaches (the Dutch side, where you’ll fly into, is known as the party side).

St. Barts: After a few days on St. Martin, hop aboard a quick 15-minute flight to St. Barts, where you’ll land on one of the shortest runways in commercial aviation. If this sounds scary, you can choose the efficient 45-minute ferry crossing from St. Martin instead. However you choose to travel, arriving at St. Barts (or St. Barths as the locals call it) will offer laid-back luxury and French refinement. Spend a few days exploring some of the 16 beaches, each with its own distinct personality, and of course chic boutiques and restaurants. (In other words, prepare to splurge a bit more on this leg of the trip.)

Guadeloupe: From St. Barts, take a one-way flight to Guadeloupe. This French territory with 12 islands offers plenty of deserted beaches and jungle hikes. The main two islands (joined by bridges) are Basse-Terre and Grande-Terre, which form a butterfly shape from above.

And beyond: Depending on how much time you have, from Guadeloupe, you can access other islands like Martinique, St. Lucia, and Antigua by purchasing affordable, one-way flights on carriers like LIAT and Caribbean Airlines .

Our St. Barths Hotel Pick: Cheval Blanc Saint Barth

Caribbean Island-Hopping Itinerary #4: Charter a Private Boat

Chartering a private sailboat or yacht to enjoy a Caribbean island-hopping vacation for a small group or family is about as dream-worthy (and splurge-worthy) as it gets. Check out family operations like BlueFoot Travel for direct bookings, or Ritzy Charters , which acts as a community marketplace for yacht and sailboat charters. You can browse a dizzying array of options to choose your perfect boat and crew with photos and reviews. It’s like booking your own private cruise.

The British Virgin Islands and U.S. Virgin Islands are some of the top places to sail in the Caribbean, thanks to excellent trade winds, crystal-clear blue water, and intricate coral reef systems. The B.V.I. and U.S.V.I. are also a lot closer together than many other island destinations, with travel times often under an hour. Whichever locations you decide to add to your yacht charter itinerary there are plenty of exciting things to do on every island.

One eight-day sample itinerary sets sail from St. Thomas where you’ll cruise to a beach in Trunk Cay, part of the U.S. Virgin Islands. Offshore you can snorkel at the Coral Reef Underwater Park Trail, which has underwater signs explaining the types of sea life you may encounter. On land, hike trails leading to old sugar plantations, or visit the snack bar on the beach. From there, sail to a friendly marina in Tortola with cafes, bars, shops, and restaurants, and then continue to a chain of southern islands in the B.V.I. Peter Island, the largest of the seven, is a popular spot for yachts and has a number of beautiful beaches for water sports like kayaking, snorkeling, stand-up paddleboarding, and scuba-diving amongst the offshore reefs.

Your next stop is The Baths on Virgin Gorda, a beach full of fascinating geological formations where you can swim, snorkel, and explore until you work up an appetite. Later, on Jost Van Dyke, you’ll find some of the best places on the trip for nightlife and live music. You’ll then visit the lush landscapes of St. John’s Virgin Islands National Park, which covers nearly all of the island. Hiking trails wind their way through the vegetation and down to the pebble beaches. There are even ancient petroglyphs carved into the rocks along the Reef Bay Trail. Aside from its natural and historical attractions, you can also find nice shops for souvenirs and upscale restaurants. The trip culminates back in St. Thomas where you’ll bid your crew (and new friends) a final farewell.

Our U.S. Virgin Islands Hotel Pick: Frenchman’s Reef & Morning Star Marriott Beach Resort

Additional Caribbean Island-Hopping Tips & Tricks

When planning your own Caribbean island-hopping itinerary, make sure to stay at least two nights at each destination. Though ambitious types might want to cross as many places (and Instagram posts) off their list as possible, you’ll be missing the point. Caribbean vacations are meant to be relaxing.

Once you get a price quote for any tour or private transfer, it’s worth the effort to call around and get additional quotes. Be sure to ask about extra charges like dock, airport, and takeoff fees.

Many flights between islands could be on a prop plane. When it comes to riding in a prop plane, don’t be shy to ask about safety. Any reputable operator should have safety information readily available, and won’t mind answering questions about their pilots. Fliers should ask if the pilot (especially if there is no co-pilot) has any health issues and if the operator (or the plane itself) has had any accidents or incidents in its history.

When chartering a boat or booking a tour, do ask about customizing the itinerary. Many companies will try to accommodate your preferences.

Pack smart! When it comes to multiple car transfers, ferries, and small planes, weight matters. Don’t expect to bring two weeks of stuff for a week of vacationing in the Caribbean. If need be, consider doing some laundry by hand while you’re in one place for a few nights. You’ll travel lighter and happier!

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The Ultimate Guide to Caribbean Island Hopping

Travel Advice

Updated: August 10, 2022

Thinking about a trip to the Caribbean , but can’t decide? How about all of them? Hear me out. Island hopping is not foreign to actual islanders. It’s nothing to take a quick flight or ferry to a nearby island to visit a friend or go to work or school. That means the infrastructure is already there.

This is also a great way to increase the list of countries you’ve traveled to in a short time- if you’re into that sort of thing. You may spend more time in the bigger islands than the smaller ones, but you can get this done reasonably. 

We’ve taken the liberty to break down these islands into groups. See which adventure is ideal for you and yours!

Close To Home Caribbean Island Hopping

The bahamas.

We could start at the Bahamas. Though the Bahamas is relatively Americanized compared to the average Caribbean island, the stark change in the climate you’ll experience there is a great way to wet your palette and prepare you for all the sun, sea and sand that is to come!

Comprised of about 700 islands , the Bahamas, in itself, is an expedition.

Start your Caribbean island hopping at Nassau, the country’s capital, which is 184 miles from Miami. This booming capital metropolitan hub offers a good blend of city and island living, as well as Bahamian culture and way of life.

You can stay on this island (New Providence) for a couple of nights, or travel to Paradise Island, which is home to the huge Atlantis resort and its massive waterpark, as well as a few other businesses. If you don’t plan on staying on Paradise Island, make a point of crossing the bridge for a small price and spending some time on Cabbage Beach. This is one of the most well-known expanses of sand in the world for sure.

Harbour Island

Get on a morning boat from Nassau to Harbour Island, where you’ll find small-island beauty and extensive lengths of soft pink sand. There are several lovely boutique hotels in this area that provide convenient access to the beach. You can also spend some time meandering around the calm lanes, seeking for pastel-hued homes and distinctive traditional Bahamian architecture.

Because Harbour Island is located just off the coast of a much larger island, Eleuthera, you can continue your journey there by water taxi (a short and inexpensive voyage).

According to those native to this island, the Gregory Town pineapple is the sweetest on the earth, and the Bahamas is thought to be the first country to produce it. While you’re here, stop by the Glass Window Bridge, a narrow walkway that connects the wild Atlantic Ocean to the tranquil waters of the Bight of Eleuthera, for some spectacular instagram-worthy opportunities. Return to Nassau by ferry from here.

How adventurous are you? You can either end your adventure in Nassau or continue on to more remote parts of the Bahamas (optional). Take another ferry from Nassau to Georgetown (Exuma Island), or take Bahamasair’s 40-minute flight to Great Exuma.

In any case, the Exumas are famed for swimming pigs, nurse sharks, colorful fish, coral reefs, marine life, boating trips, on-island tours, and kilometers of rarely-visited beaches. There is plenty of activities to keep you busy for days.

Puerto Rico

Still not fully out of the woods (the US) yet! If you’ve been to the Bahamas, or you want immerse yourself in a country with a different language, here’s your best first stop.

Explore the pastel homes, cobblestone streets, and 500-year-old fortification of Castillo San Felipe del Morro in Puerto Rico. Take a tour of the Museum of Contemporary Art, a distillery where you may sample barrel-aged rum, and walk or bike along the beautiful Condado Beach region.

The Small Islands

Speckled across the Eastern side of the Caribbean are the small islands. You will be awash with options regarding culture, food, and language during your Caribbean island hopping adventure.

Because of the superb trade winds, crystal-clear blue water, and complicated coral reef systems, the British Virgin Islands and the United States Virgin Islands are among the best places to sail in the Caribbean. The British Virgin Islands and the United States Virgin Islands are also much closer together than many other island locations, with travel times frequently under an hour. There are lots of fun things to do on every island, regardless of which destinations you choose to include in your yacht charter itinerary.

The British Virgin Islands

The BVI are made up of 32 smaller islands and four bigger islands: Tortola, Virgin Gorda, Jost Van Dyke, and Anegada. The BVI has a total size of 59 square miles. To the northeast of the US Virgin Islands are the British Virgin Islands.

Just north of Puerto Rico is the BVI. Take a ferry from Tortola to Jost Van Dyke to see the naturally frothing Bubbly Pool. At Virgin Gorda Baths, you can swim, snorkel, and explore the stunning rock formations. On a zipline excursion, soar high above the island’s jungle canopy before relaxing on a palm-shaded white sand beach.

US Virgin Islands

The USVI are made up of four main islands: St. Croix, St. Thomas , St. John , and Water Island, as well as 50 smaller islets and cays. The USVI has a total area of 133 square miles.

On St. Thomas, the vibrant, flower-filled Charlotte Amalie is a beautiful cruise port, with incredible snorkeling, sailing, shopping, and sightseeing opportunities. On city excursions, see sights including Bluebeard’s Castle, Villa Botanica, and the 99 Steps. On a culinary tour, sample Caribbean and Creole-influenced cuisine. Drink a Painkiller or a Bushwacker, two popular cocktails on the island.

St. Martin (St. Maarten)

While you’re in the area, why not make a stop? A day-in trip to Philipsburg, St. Maarten, has a dual purpose, allowing visitors to see both the Dutch and French portions of the island. Stroll right off your cruise ship to Great Bay Beach, where a chaise and sun umbrella await you on pristine white sand during your Caribbean island hopping holiday.

Shopping duty-free in Philipsburg and then traveling to Marigot on the French side for refined gastronomic excursions are two of the top things to do in St. Maarten. Spend the day boating the pristine blue waters around the island, snorkeling, or semi-submarining to discover the colorful undersea life.

La Désirade is a little island off the coast of Guadeloupe that embodies everything you love about the Caribbean: palm-fringed beaches, dense vegetation, and laid-back island life. 

Numerous secluded white-sand beaches, including Plage Anse Petite Riviere, benefitting from calm waters due to an offshore reef. The only way to get to La Désirade is by ferry from Grande-Terre, which departs twice daily from St-François.

Dominica, Martinique, and St Lucia are all easily accessible from Guadeloupe, as are Montserrat , St Kitts & Nevis, and Antigua and Barbuda. Let’s zoom in on a few.

The island is covered in silky white sand and surrounded by crystal-clear water. It is the wonderfully luxuriant scenery – particularly the island’s distinctive twin volcanic peaks, Gros and Petit Piton – that elevates the island’s sandy stretches to new heights.

Whether you want to relax in the sand with a book and a beer while admiring the beautiful mountain vistas, or you want to go a little more active on your beach vacation, St. Lucia has you covered. 

Antigua and Barbuda

Many of Antigua’s 365 beaches are flanked by large and small resorts, both modest and extravagant. English Harbour is known for its yachting antics as well as its historic sites. The beautiful Frigate Bird Sanctuary is located on Barbuda, the sister island.

St. Kitts and Nevis

St Kitts, like Nevis, features large hotels and burgeoning condo complexes. It’s just big enough for a day tour across the island, which includes a visit to the massive pirate-era Brimstone Hill Fortress.

The Big Islands

Some islands require more than a day to get a full experience and more than a ferry to travel in between.

The Greater Antilles include Hispaniola (which is now Haiti and the Dominican Republic), as well as Cuba, Jamaica, and Puerto Rico.

Jamaica, one of the Caribbean’s most beautiful islands, is the stuff of tropical fantasies: stunning beaches, lush rainforests, spectacular waterfalls, languid rivers for rafting, and caves to explore. Coffee plantations may thrive because the highlands are high and cool enough, and the West Indian civilization is steeped in history.

Sample the island’s flavors, including everything from jerk chicken to coffee and rums. Explore stately historical sites, relax in the beautiful outdoors, and allow reggae beats to transport you to a state of complete relaxation during you Caribbean island hopping adventure.

Particularly at night, Havana comes to life. There, the Fabrica de Arte Cubano is a converted cooking oil factory that hosts regular electronic music evenings with live DJs, concerts, and photographic and cinematic art exhibitions. Don’t forget to visit Trinidad’s nightclub, which is nestled in a local cave!

The Dominican Republic features almost 1,000 kilometres of beautiful sand beaches with crystal pure blue sea. If you’re seeking for ultra-luxurious resorts with pools and golf courses, some beaches are ideal. If you’re searching for something a little more off the beaten path with less people, you’ll have no trouble finding it! The beaches that encircle the country are all beautiful in their own way. The beaches are beautiful and a nice location to unwind.

Windsurfing, kitesurfing, and normal surfing are all popular on Puerto Plata’s north side “Cabarete Beach.” It’s also a fantastic spot for paragliding.

Specifically in Haiti, three deep blue pools are joined by beautiful waterfalls at the Bassins Bleu Falls. These waterfalls have a unique color due to the minerals found in the water. Water nymphs, according to legend, live in caverns near the waterfalls and enjoy the sun on the rock at Palm Lake. However, they vanish whenever they hear footsteps.

Mainland Caribbean Hopping

We cater to all types of travelers here. You may not be the typical tourist who is enraptured by the eastern Caribbean. Maybe you want a different experience. Ancient ruins and numerous eco-adventures on land and sea can be found on the Caribbean’s western islands. Go island hopping on a Western Caribbean cruise to Mexico, Belize, and Honduras.

Cozumel is known for its fantastic diving locations, conveniently accessible Mayan ruins, and gorgeous blue waters, and it has something to offer everyone. Dive in the Arrecifes de Cozumel National Park to see living reefs, beautiful fish, stingrays, nurse sharks, and marine turtles.

Plan beach time and a swim with playful dolphins, subterranean cave exploration, a submarine tour, or a visit to a sea turtle farm in Cozumel for family-friendly activities. Visit the amazing Mayan remains at San Gervasio on Cozumel, or take a ferry to Tulum to see the ruins.

During airboat adventures, see magnificent native animals and dive in some of Belize’s best beaches. Take a riverboat ride down a lagoon, stopping in Lamanai to see Mayan ceremonial ruins. Trek through the forest before cooling off with a river tubing adventure or floating through an old Mayan cave, lagoon, and waterfall.

When you dock in Costa Maya, you’ll discover that the region’s reputation for stunning beaches and abundant marine life is well-deserved. Banco Chinchorro, the Northern Hemisphere’s largest atoll reef, sits located off the coast and offers snorkeling and diving opportunities.

To get to the Mayan ruins at Chacchoben, take a ride through the rainforest or take a salsa-making class and a salsa-dancing lesson on the beach.

Snorkel the Mesoamerican Reef and witness rainbow starfish at Starfish Alley in Roatan, Honduras, or swim at West Beach. Visit Little French Key to observe sloths and monkeys, and visit the Roatan Rum Company to sample rum straight, in chocolate, or in rum cake.

Does anything tickle your fancy for Caribbean island hopping? The options are overwhelming, but you’re sure to find a package that is perfect for your taste! Are you done packing yet?

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Caribbean Island-Hopping: Why A Cruise is the Way to Go

By Carnival Cruise Line

A vacation planned around Caribbean island-hopping is certainly bound to be a unique, exciting and memorable trip. With so many Caribbean islands so close to one another, island-hopping lets you easily visit multiple destinations in a short period of time. This also allows you to experience the fun, beauty, culture, food and attractions of many different places all in one trip!

While there are many options for planning a Caribbean island-hopping vacation on your own, the best and easiest way to visit many of the islands and really enjoy all they have to offer is with a cruise to the Caribbean . Carnival® offers many options for visiting these amazing tropical locales, and each Carnival cruise ship lets you choose which islands you visit.

Take the time to browse through the choices for Western Caribbean Cruises and Eastern Caribbean Cruises , then read on to discover why Caribbean cruises from Miami, Ft. Lauderdale, Tampa, New York and Galveston are the best way to experience island-hopping in the Caribbean!

No Need to Worry About Transportation

Planning to island-hop in the Caribbean involves lots of travel and transportation plans. Aside from the costs quickly adding up, organizing reliable, quick and safe transportation options can also be quite stressful.

With Carnival ® , however, a Caribbean cruise includes transportation to a number of different islands, so you can simply enjoy your vacation with your friends or family.

And the best part is that while you are at sea, you can enjoy the numerous activities onboard the ship, watch entertaining shows and partake in the delicious dining options offered by Carnival Cruises!

You Get a Lot More For Your Money

Caribbean island-hopping on your own also means booking multiple hotels or resorts. This can be very expensive, and it also means you’ll waste a lot of time packing and unpacking at each destination, not to mention traveling to each accommodation.

A Caribbean cruise, however, is as luxurious as staying at an all-inclusive resort throughout the length of your trip and all for one affordable price. You don’t have to worry about finding accommodations at each island, and you’ll only unpack once when you arrive on your cruise ship!

Flexibility to Choose Your Itinerary

Because Carnival offers cruises to the Caribbean of varying lengths and with different destinations, you’ll have more flexibility in choosing which islands you’d like to visit. You don’t have to worry about one location being too far away to travel to on your own, simply because the cruise ship will take you there.

And, with many shore excursions available at each port of call, you’ll get the chance to enjoy some of the best beaches, attractions, food and scenery each Caribbean island has to offer!

It’s the Best Way to Relax and Enjoy Your Vacation

So the transportation and accommodations are already taken care of, and because you also get to pick and reserve your excursions in advance, all that’s left for you to do is relax and enjoy every minute of your cruise!

That means you get to truly maximize your vacation time and eliminate all the planning and research you’d normally have to do if planning to go Caribbean island hopping on your own.

No rushing to catch flights or boats to the next island, no rushing to pack and leave your hotel before check-out and no time wasted on researching where to go once you reach each island. It’s all taken care of for you!

You Can Truly Immerse Yourself in Each Destination

With more time to spend enjoying each island, you can immerse yourself in the culture of each island. The variety of excursions allows you to pick activities and attractions that cater specifically to you, so you can make the most of each port of call.

Whether you just want to relax on a white sand beach while sipping a cocktail, or if you want to explore an island on an ATV, you’ll find shore excursions let you do all of the above and much more!

In addition to the opportunity to visit multiple islands, you’ll enjoy onboard activities, pools, restaurants and entertainment. And you’ll definitely be bringing home cherished memories, lots of great photos and some unique souvenirs!

Whether you choose to cruise to the Caribbean from New York or from Miami, a cruise is the best way to go Caribbean island-hopping. Skip the stress of planning a vacation featuring multiple destinations and book a Caribbean cruise instead. All you need to do is decide whether you want to visit the Western Caribbean or the Eastern Caribbean, and leave the rest to Carnival!

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How to Go Island Hopping in the Caribbean

Last updated: November 6th, 2023

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Cruising is the easiest, most carefree way to go Caribbean island hopping. It’s the only form of travel that transports you in style in luxuriously appointed staterooms.

As you sail between islands, you can be pampered at onboard spa and fitness centers, be entertained with live theater and musical performances, and dine on world-class cuisine served in beautifully designed venues—all before you ever set foot on an island.

With a cruise, there’s no worrying about booking hotels or finding island-to-island transportation, which is often inconvenient and time consuming.

Here are some Caribbean island-hopping adventures you can embark on during your next vacation.

Southern Caribbean Island Hop

Cruise to the Southern Caribbean and note the diverse cultural and historical backgrounds that give each island its flavor and charm.

Watch: Southern Caribbean Cruises on Celebrity Cruises

St. Maarten’s alluring beaches are as perfect for diving and snorkeling as they are for leisurely sunbathing, making it one of the best Caribbean islands for families . Visit the French side of the island to indulge your senses and create your own scent at a perfume factory, or walk with one of our onboard chefs on a day of culinary discovery.

The Pitons, St. Lucia

A day spent in St. Lucia on the stunning crystal-white Sugar Beach is surpassed only by the sight of the twin peaks of the Pitons visible across the bay. Hike to the summit of Gros Piton, a UNESCO World Heritage Site, or zipline over trees in sight of the twin peaks.

Other exciting things to do in St. Lucia include horseback riding on Cas en Bas Beach or discovering the colorful undersea marine world on scuba, snorkel, or SNUBA excursions.

Harrison’s Cave, Barbados

For a perfect family day in sun-drenched Barbados , board a catamaran and swim with sea turtles. Explore the bubbling streams, stalagmites, and stalactites of Harrison’s Caves. Snorkel through shipwrecks or unwind under the shade of a palm tree while watching the calm blue sea lap the pristine shores.

St. John’s, Antigua

Jerk chicken, pineapple salsa, and coconut tart are on the menu when you visit the seaside home of a local chef in St. John for a hands-on cooking class, garden tour, and rum punch tasting. It’s one of the most exciting things to do in Antigua for a taste of Caribbean culture and hospitality.

Venture into breathtaking areas of the island on a 4×4, traveling through a rainforest on the way to a swim in one of the best beaches in Antigua . Sink your toes in the white sand, parasail, water ski, or have a snack at a beachfront stand.

The islands of St. Kitts and Nevis are small, secluded and charming. Explore rainforests, dormant volcanoes, lush flora and fauna, and beaches with stunning views of the Atlantic and Caribbean coasts.

Ride a double-decker sightseeing train to get a feel for St. Kitts’ charms. Savor West Indian cuisine on Nevis, sample local rum, and relax on the stunning golden sand at some of the best beaches in the Caribbean .

Stroll through Oranjestad , Aruba’s capital, and be charmed by the candy-colored houses and Dutch architecture. Glide along crystalline Caribbean waters on a catamaran cruise and go on a snorkeling adventure, or board a schooner cruise and admire the sunset while sipping on a tropical cocktail.

Read: Best Places to Snorkel in Aruba

At Kralendijk, Bonaire , watch pink flamingos walking on salt flats, tour the island on a bike, board a semi-sub explorer to see tropical fish and marine life, or snorkel the coral reef-ringed island whose coastline is a national marine park.

Curacao liqueur

Bring your dive card for a two-tank, certified dive on Curaçao , one of the best Caribbean islands for diving, or snorkel with stingrays and feed nurse sharks at Sea Aquarium Park.

In colorful Willemstad, one of the most stunning places to visit in the Southern Caribbean islands , browse the outdoor market or sit at a terrace cafe and look out over stunning Mambo Beach while sipping a cocktail made with the island’s famous blue Curaçao liqueur.

Read: Best Caribbean Islands for Couples

Island Hopping in the Eastern Caribbean

Go island hopping in the alluring Eastern Caribbean on a cruise from Fort Lauderdale or Tampa that visits destinations like San Juan, Puerto Rico; Charlotte Amalie, St. Thomas; Tortola, British Virgin Islands; Nassau, Bahamas; St. Kitts and Nevis; Puerto Plato, Dominican Republic; and Key West, Florida.

Read:  Things to Do in Fort Lauderdale With Kids

Watch: Eastern Caribbean Cruise on Celebrity Cruises

In Puerto Rico , explore beautiful Old San Juan’s pastel buildings, cobblestoned streets, and the 500-year-old fortress, Castillo San Felipe del Morro. Visit the Museum of Contemporary Art, taste barrel-aged rum at a distillery, and walk or bike along the stunning Condado Beach area.

Virgin Gorda Baths, British Virgin Islands

On beautiful Tortola , hop a ferry to Jost Van Dyke to view the naturally foaming Bubbly Pool. Swim, snorkel, and explore the breathtaking rock formations at Virgin Gorda Baths. Soar high above the island’s jungle canopy on a zipline adventure, then relax on a palm-shaded white sand beach.

Philipsburg, St. Maarten

A day in port at Philipsburg, St. Maarten does double-duty with time to explore both the Dutch and the French sides of the island. During your Caribbean island-hopping vacation, stroll right off your cruise ship to Great Bay Beach, where a chaise and sun umbrella await on powdery white sand.

Some of the best things to do in St. Maarten include shopping duty-free in Philipsburg, then heading over to Marigot on the French side for sophisticated culinary adventures.

Experience sailing in the Caribbean and explore the clear blue waters around the island or discover the colorful undersea life on snorkeling or semi-submarine adventures.

Charlotte Amalie, St. Thomas

Vibrant, flower-filled Charlotte Amalie on St. Thomas is a dream cruise port, with exceptional opportunities for snorkeling, sailing, shopping, and sightseeing. Discover landmarks like Bluebeard’s Castle, Villa Botanica, and the 99 Steps on city sojourns.

Go shopping in St. Thomas on Main Street for duty-free everything, from souvenirs to spirits. Taste Caribbean- and Creole-influenced food on a culinary tour. Sip a Painkiller or Bushwacker, two of the island’s favorite cocktails.

Puerto Plata, Dominican Republic

Explore the 27 dazzling waterfalls of Damajagua when you island hop to Puerto Plata in the Dominican Republic. Watch rescued squirrel monkeys roam the jungle as you zipline above, visit the Amber Museum, or head to the beach to surf.

Read: Best Beaches in the Dominican Republic

Western Caribbean Island Hop

The western islands of the Caribbean boast ancient ruins and multiple eco-adventures on land and sea. On a Western Caribbean cruise , go island-hopping to places like Cozumel, Mexico; Georgetown, Grand Cayman; Belize; Roatan, Honduras; and Key West.

Watch: Western Caribbean Cruise with Celebrity Cruises

Equally famous for its fabulous diving sites, easily accessible Mayan ruins , and clear turquoise waters, Cozumel offers activities for every kind of traveler. Dive at the Arrecifes de Cozumel National Park to witness incredible underwater sights like living reefs, colorful fish, stingrays, nurse sharks, and sea turtles.

For family-friendly activities in Cozumel , plan beach time and a swim with playful dolphins, explore underground caves, take a submarine tour, or visit a sea turtle farm.

Tulum in Cozumel, Mexico

Explore the fascinating Mayan ruins at San Gervasio on Cozumel, or ferry over to see the ruins of Tulum.

Either way you turn in Belize , to the east for gorgeous Caribbean views or the west for lush jungle, you’ll thoroughly enjoy a day in port.

See amazing native wildlife during airboat adventures and snorkel in some of the best Belize beaches . Board a riverboat for a safari down a lagoon with a stop at Lamanai to explore Mayan ceremonial ruins. Trek through the jungle, then cool off on a river tubing trip, or float through an ancient Mayan cave, lagoon, and waterfall.

Read: Unforgettable Adventures in Belize

Costa Maya, Mexico

Docking in Costa Maya , you’ll find that its reputation for beautiful beaches and vibrant marine life is no exaggeration. Explore the underwater world during snorkeling or diving explorations at Banco Chinchorro, the Northern Hemisphere’s largest atoll reef, just off the coast.

Ride through the rainforest to reach the Mayan ruins at Chacchoben, or take a salsa-making class and a salsa dancing lesson on the beach.

Shipwreck in Mayan Riviera, Mexico

In Roatan, Honduras , snorkel the Mesoamerican Reef and see multicolored starfish at Starfish Alley, or visit West Beach for a swim. Head to Little French Key to see sloths and monkeys, and savor the flavor of rum straight, in chocolate, or in rum cake at the Roatan Rum Company.

Read: Best Caribbean Rum Tours & Tastings

Stingray City in George Town, Grand Cayman

At Grand Cayman’s Seven Mile Beach, swim with gentle Southern stingrays and bottlenose dolphins, scuba or snorkel around shipwrecks, or unwind on a beach chaise with a drink in hand.

Pause for a barbecue lunch or conch chowder, then shop for souvenirs at open-air markets and duty-free boutiques.

Read: Western Caribbean Islands & Destinations Worth Exploring

Duval Street in Key West, Florida

When you cruise to quirky, cool, and colorful Key West , head out into the water on paddleboarding, parasailing, or kayaking tours. Board a catamaran for a swim and snorkel adventure to see the only coral reef in the continental United States.

Bike the length of Duval Street, stopping for a fresh seafood lunch. When you tour Ernest Hemingway’s house, be sure to look for the six-toed cats that live there.

Go Caribbean islands hopping on a luxury cruise vacation with Celebrity Cruises. Browse our Caribbean cruise itineraries and book your next vacation online.

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Caribbean Island Hopping | 7 Islands in 1 week 

By: Author Hannah

Posted on Last updated: 23 May, 2023

There are over 7,000 islands in the Caribbean, of which only 2% are inhabited. One of the best ways to get a taste of a bunch of islands is going on a Caribbean island-hopping cruise.

On our recent classic Caribbean cruise with Windstar Cruises, we visited 7 islands in 1 week. Most Caribbean cruises depart from Florida but our Windstar cruise departed from St. Maarten. This gave us the option to do a little more Caribbean island hopping on and after our cruise.

Each day we’d wake up in a different port to explore a new island. We had an epic week at sea on the Wind Surf cruise ship , here is what our week of Caribbean island hopping looked like.

Caribbean Island Hopping With Windstar Cruises

Our Windstar cruise started and ended in Philipsburg, St. Maarten. We arrived late in the evening and spent the night at Mercure St Martin . The next morning we headed to the port to board our ship the Wind Surf.

We basically just dropped our bags and jumped in a shuttle to Maho Beach for $16 per person round trip. One of the best things to do in St Maarten is head to Maho Beach and watch the planes land. We knew we wanted to spend the afternoon on the beach watching the planes literally land right above our heads and feel the jet blast when they take off.

Make sure to visit Sunset Beach Bar on Maho Beach and check the surfboard with all the arrival times. However, the board doesn’t have all of the flights. If you have access to the internet, the best schedule you can find here at the official SXM airport arrivals page .

Keep in mind the planes often land ahead of schedule, and of course sometimes behind. We probably watched at least 20 planes land. In between landings we hung out at the bar, the drink prices were reasonable at Maho Beach, $4 a beer and $9 daiquiris but happy hour is 2 for 1.

We suggest spending at least one night in Phillipsburg either before or after your Caribbean cruise. There are several excursions in St. Maarten ( click here for a whole bunch bookable online) including some day trips to nearby islands.

• Anguilla Day Trip
• Prickly Pear Sailing Day Trip
• Saba Day Trip
• St. Barts Sailing & Snorkeling

St. Maarten is also a great place to catch a ferry to other nearby Caribbean islands. We jumped on an Anguilla ferry and spent 5 nights continuing our Caribbean island-hopping adventure. If you happen to really enjoy St. Barts you can catch a ferry from St. Maarten to St. Barts, make sure to check out some of the best beaches in St Barts .

• St. Maarten to Anguilla  ferry schedule and  book online here
• St. Maarten to St. Barts ferry schedule and book online here

After our cruise, we took the ferry to Anguilla and spent 5 nights at  CeBlue Villas . If you do head to Anguilla we highly suggest renting a car in Anguilla it’s the best way to explore the island.

We spent most of our days driving to all the different beaches on the island, eating at the best restaurants in Anguilla , relaxing in our private pool, but our favorite day was spent on Sandy Island  where we had the best lobster of our lives. There a ton to do and see in Anguilla .

If you love walking on the beach for miles and miles head to Barbuda. Barbuda has crazy clear water and pink sand beaches that are actually pink! We only spent 5 hours on Barbuda but we literally walked the beach the entire time.

The beaches are deserted we only say one little place that appeared to maybe have some cold beers. There was only one offshore excursion in Barbuda to the Frigate Bird Sanctuary. Which is the world’s largest frigate birds nesting with 2,500+ birds. We did see tons of Frigatebirds but we weren’t bird watching, we were watching out for them when flying our drone . We were after gorgeous aerial shots of Barbuda like this.

NOTE: You can take a ferry from Barbuda to Antigua.

Dominica is known as the nature island in the Caribbean complete with lush rainforest, volcano peaks, hot springs, waterfalls, snorkeling, and much more.

We spent the day hiking in the Morne Trois Pitons National Park. We were high up in the rainforest crossing several rivers with spectacular views (when it’s not raining). There are over 300 miles of hiking trails in Dominica we hope to get back to do some more hiking in Dominica.

NOTE: You can take a ferry from Dominica to Guadeloupe, Martinique, and St. Lucia. 

Our home for the week the Wind Surf anchored in St Lucia.

St. Lucia 

There are tons of offshore excursions in St. Lucia but if you prefer to chill on the beach Windstar sets up a beach BBQ on Pigeon Island. They transform the beach into their own private club for the day complete with beach chairs, umbrella drinks, water sports, jerk chicken, and much more.

We booked a half-day private car to explore the island and got back to Pigeon Island just in time for lunch.

We loved our time in St Lucia and returned a year later and spent a week on the island at Sandals La Toc & Sandals St Lucian Grande. The two properties are way different, make sure to pick the best Sandals Resort for you. We preferred Sandals St. Lucian Grande .

When we were on Pigeon Island we could see the overwater bungalows at Sandals St. Lucian Grande . We were in awe and 3 weeks later we returned to St. Lucia and had the opportunity to stay in them!

We also didn’t have a chance to visit the Piton’s during our cruise so on our return trip we went on Pitons sunset & snorkel cruise. There are also Martinique day trips from St. Lucia, click here for details.

NOTE: You can take a ferry from St. Lucia to  Martinique, Dominica, and St. Lucia.

Les Saintes, Guade loupe

Guadeloupe surprised us the most. We didn’t know much about the island, but we now know we’ll be going back. We spent the day out on a boat exploring the Les Saintes islands. Gorgeous beaches and volcanic hillsides. The water reminded us of our favorite islands, El Nido in the Philippines.

NOTE: You can take a ferry from Guadeloupe to Dominica, Martinique, and St. Lucia.

Basseterre is often referred to as one of the prettiest Caribbean’s capital cities. So we made sure to save a few hours to explore the city. Adam went diving in St. Kitts in the morning while I was being pampered at the spa on the Wind Surf. There are often port day specials in the spa and I highly recommend getting a massage.

NOTE: You can take a ferry from St. Kitts to Nevis.

St. Barts is where the rich & famous come to play. The marina is full of million-dollar yachts and the shopping is top-notch (don’t forget your wallet). We spent the morning on a catamaran tour around St. Barts with a great snorkeling & beach stop at one of the best beaches in St Barts .

After snorkeling, we took the tender into Gustavia. We highly suggest renting a car to explore the island, this is the most affordable option to see most of the island. We opted to walk over to St. Jeans Bay, which was only 20 minutes from Gustavia.

Along the way we literally had the planes landing over our heads just like in St. Maarten at Maho Beach. However, the planes here have a very tricky landing! We recommend walking to the intersection to watch it in front of the runway.

NOTE: You can take a ferry from St. Barts to St. Maarten, click here for schedule & rates. 

Pin me for later!

We had an amazing time on our Windstar cruise and in one week of Caribbean island hopping we covered 7 islands (6 new to us). If you aren’t sure what island you’d like to spend a week vacation at, consider going on a Caribbean cruise first to get an idea of what some islands are like. We now have a few more islands on our bucket list we can’t wait to get back to. 

Thank you to Windstar Cruise Line for hosting us on such an epic Caribbean cruise! As always all opinions are our own.

Saturday 15th of June 2019

Hoping to go island hopping for my 30th and this was SO helpful. Thank you!

Tuesday 25th of June 2019

Have a great trip & birthday!

PHEDRA DUBE

Wednesday 25th of July 2018

Are there any cruises that last longer than 7 days and allows more than a one day, same island visit?

Sunday 29th of July 2018

Generally, most cruises do not have multiple days in the same port. https://www.gettingstamped.com/wp-admin/edit-comments.php#comments-form

Saturday 1st of July 2017

Beautiful places. I bet you have a lot of fun on your trips.

Hannah Lukaszewicz

We visited some amazing places on our Caribbean island hopping cruise with Windstar Cruises. We had a blast!

• A Beginners Guide To Island...

A Beginner's Guide to Island Hopping in the Caribbean

Freelance Caribbean Writer

You can easily take in a string of delicious Caribbean destinations on a single trip by mastering the art of island-hopping. Our guide to small island-hopping shows you how with must-visits and travel tips and learning more about the Caribbean culture.

Did you know you can now travel with Culture Trip? Book now and join one of our premium small-group tours to discover the world like never before.

The close proximity of the Caribbean’s small islands makes them ideal for a hop, skip and a jump from one to the other in a daisy chain of island explorations. Fancy diving down to a shipwreck in Aruba one day and getting up close with flamingos on Guadeloupe the next? Then read on…

Where to visit in the Caribbean

The island of St Martin (or St Maarten) is a great destination to start exploring the eastern side of the Caribbean. It’s divided roughly down the middle between the French Republic and the Kingdom of the Netherlands, and so it offers visitors a two-nation vacation. The Dutch side of the island is known as the party side for hosting the Heineken Regatta, a four-day sailing race with concerts and other festivities. Meanwhile, in true French fashion, the other side of the island features quaint, romantic restaurants , designer boutiques and nude beaches .

From St Martin, journey to the islands of Anguilla and enjoy its secluded coves, before heading to St Barts to do some celebrity spotting and Saba , which is known for its diving site at Saba Marine Park. Puerto Rico, the jewel of the Caribbean, is also a popular choice. The island is known for its cuisine – a mixture of Spanish, African, and Taino – plus its strong rum.

Elsewhere, you can get pretty much anywhere in the Caribbean from San Juan (thanks to regional carriers such as Cape Air and Seaborne), and a number of islands are even closer by ferry and plane, such as Culebra, Vieques, British Virgin Islands and the US Virgin Islands. The Dominican Republic is also only a very short flight away.

You can do all the island-hopping you want in the Guadeloupe Islands and stay within the same territory. This beautiful archipelago has five islands within easy reach by ferry and air from the main island of Grande Terre/Basseterre, each with its own character and flavor, from tiny Terre-de-Haut to beach paradise Marie Galante. From Guadeloupe, you can easily access the islands Dominica , Martinique and St Lucia below and Montserrat , St Kitts and Nevis , and Antigua and Barbuda.

The so-called ‘ABC’ islands of Aruba, Bonaire and Curacao , at the western edge of the Leeward Antilles chain, are also a popular island-hopping loop. Aruba is a popular tourist destination with several big-name beach resorts; Bonaire is best known in scuba-diving circles for its spectacular undersea life; Curacao charms with its Dutch-influenced architecture.

Must-visits on your multi-island trip

St Martin is famed for its white-sand beaches but there’s one that stands out from the rest. Maho Beach, which lies near the airport, is where tourists come to photograph planes passing just feet above their heads as they swoop in to land. If you prefer natural wonders, catch the ferry to Pinel Island in St Martin’s Nature Reserve, where you’ll find palm-fringed sands and shallow waters ideal for snorkeling . To learn about the island’s Dutch heritage, take a trip to Fort Amsterdam near Philipsburg. Here, you can explore the ruins of this former military base and take in sweeping hilltop views.

There’s no shortage of historic sites in Puerto Rico . Start by touring grand La Fortaleza, the governor’s official residence, which was built between 1533 and 1540 to defend the harbor. Continue to the island’s longest-serving settlement, Old San Juan, a National Historic Site filled with 16th-century fortresses, cathedrals and cobbled streets. For a change of pace, you can hike rainforest trails to crashing waterfalls in El Yunque National Forest or relax in hillside thermal hot springs in Coamo. When the sun goes down, marvel at Puerto Rico’s bioluminescent waters in Mosquito Bay, which light up when touched.

If you’re visiting Guadeloupe , don’t miss Jardin Botanique. This seven-acre haven, in the heart of the islands, showcases exotic Caribbean flora and birdlife. Think bamboo forests and pink bougainvillea, flamingos and arboretums. If you can drag yourself away from Guadeloupe’s pristine beaches, spend a day at Carbet Falls in the National Park. These three waterfalls cascade down a mountain surrounded by tropical rainforests and hiking trails. Looking for the perfect sunset? Then head to Pointe des Châteaux, a clifftop peninsula on the eastern end of Grande-Terre where you can watch waves crash onto the rocks.

Divers flock to Aruba to explore its famous Antilla Shipwreck, a German war ship blanketed in coral and tube sponges. Aruba’s other key attraction is swanky Renaissance Island where pink flamingos tip-toe through the shallows. Hop over to Bonaire for more unspoilt Caribbean sands, including 1,000 Steps Beach and Klein Bonaire, a tiny uninhabited islet set in a marine park where turtles nest. Nearby Curacao is the perfect place to get a glimpse into the Caribbean’s Dutch past in its capital Willemstad, Unesco-listed for its colorful colonial architecture. Don’t miss Curacao’s Hato Caves either, which were formed over 300,000 years ago from marine coral limestone and contain Amerindian Arawak cave drawings.

How to travel

There are a few options for island-hopping in the Caribbean. The most popular is booking a cruise, but you can easily go it alone and create your own island-hopping loop by taking advantage of the numerous ferries that go back and forth between all of the islands.

Alternatively, charter a boat – it’s not as expensive as you might think. You don’t even need to know how to sail as many come with skippers included in the price.

Catching a flight should be your last resort. Though traveling by air to the smaller islands in the Caribbean is relatively inexpensive, it’s not environmentally friendly. This option makes sense only in cases where the islands have a significance distance between them.

Safety tips

If you are wondering when is the best time to visit Caribbean, this is what we recommend – it’s best to plan your island-hopping loop in either spring or at the beginning of summer, when the weather is calm. The Atlantic hurricane season starts in early June and runs until the end of November, while most of the storms hit during peak hurricane season between August and October.

Meanwhile, all major Caribbean islands have excellent mobile coverage. But for those islands with a very small population, such as Culebra and Vieques near Puerto Rico, a portable radio might come in handy. Sunscreen, mosquito repellant and bottled water should too always be in your luggage.

Amy Blyth contributed additional reporting to this article.

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A Guide to Island Hopping in the Caribbean

Many Caribbean islands are very close together– so why not visit more than one?

If you just can’t get enough of the Caribbean, perhaps island hopping is for you. It’s all about visiting more than one island during your Caribbean vacation.

The first thing you might think of when you hear the term “island hopping” is embarking on a Caribbean cruise. Many Caribbean cruises allow travelers to visit several islands over the course of a few days.

However, cruising has one huge disadvantage: you can’t create your own schedule. You’ll only be able to spend the allotted amount of time on each island, and you have to adhere to a strict schedule in order to avoid being left behind!

So how can a free-spirited, flexible traveler visit several Caribbean islands without being bunkered down in a luxury liner?

Simple: take a look through our quick guide to island hopping in the Caribbean. We’ll give you an idea as to which Caribbean countries are in close proximity to each other, allowing for easy travel between islands.

From St. Martin

The island of St. Martin is a great place to begin if you’re keen on visiting the eastern Caribbean islands. First of all, the landmass of St. Martin itself is divided into two countries: St. Martin and Sint Maarten. While St. Martin offers French elegance, Sint Maarten presents Dutch charm. After exploring both sides, you can visit the nearby Caribbean island countries of Anguilla , Saba, and St. Barthelemy .

Travel Information for St. Martin–Sint Maarten–Anguilla–Saba–St. Barthelemy

We suggest flying to St. Martin from your home country, since it has a larger airport than the smaller nearby eastern Caribbean countries. Princess Juliana International Airport in Simpson Bay offers direct flights to and from the US, Europe, South America and the Caribbean. As for entry and immigration requirements, citizens of France, Canada, the United States, and several other countries do not need a visa. Consult entry requirements by country here .

Once you have arrived in St. Martin, you can spend some time in one country, and then simply cross over to the other. Since there’s no physical border between the Saint Martin and Sint Maarten, people and goods can travel in and out freely. In fact, the border between these two nations is known for being one of the most peaceful borders in the entire world!

Next, you can travel to the neighboring island of Anguilla via ferry. Public ferries run daily, at 45-minute intervals. You can also book a private ferry boat for a higher price. In addition, you can take ferries to Saba and St. Barts from St. Martin.

See schedules and book ferries from St. Martin to Anguilla, Saba, or St. Barts here .

From Puerto Rico

Puerto Rico is a US commonwealth located in the northeast Caribbean Sea. It consists of one main island and several tiny islands on which several thousand people live.

Travel Information for Puerto Rico–Vieques–Culebra–Dominican Republic–Haiti

You can catch flights from many countries to Puerto Rico’s main airport in San Juan. From there, you can take inexpensive ferry rides to Culebra and Vieques, two gorgeous islands off the coast of this US territory. Then, you can either travel by ferry or by plane to the Dominican Republic. It’s a quick trip and often costs less than $100 for a plane ticket from San Juan to Santo Domingo. Once you’ve explored the Dominican Republic, you can cross the border to Haiti, since these two countries are both located on the island of Hispaniola. (Keep in mind that entry requirements may be different for each country).

Click here to see information about the ferry route from San Juan, Puerto Rico, to Santo Domingo, Dominican Republic.

Other short flights are available from Puerto Rico to many other islands in the Caribbean. Regional carriers like Cape Air and Seaborne make this possible. Some of the closest islands to Puerto Rico, besides the Dominican Republic, are the British Virgin Islands and the US Virgin Islands.

From the ABC Islands

Within the Leeward Antilles chain of islands in the Caribbean lie the ABC islands. Aruba, Bonaire, and Curacao are in close proximity to each other, making island hopping between them easy. Aruba is a laid-back, luxurious island belonging to the Kingdom of the Netherlands. Bonaire is well-known for its coral reefs and marine life, making it a fabulous island for snorkeling and scuba diving. Curacao is a charming Dutch island famous for its quaint European architecture and rich cultural history.

Travel information for the ABC islands

You can visit all three ABC islands in just one trip! To do so, however, you’ll need to charter a boat or buy a plane ticket. If that seems too impractical, don’t lose hope just yet– the minister of transport has announced plans for providing fast ferry service between Aruba, Bonaire, and Curacao in the near future.

From Saint Lucia

Saint Lucia is a gorgeous island with some top-notch resorts, and easy access to various other Caribbean islands. Once you have arrived, you can easily take a ferry boat to Martinique, Guadeloupe, and Dominica!

Travel information for Saint Lucia–Martinique, Guadeloupe, and Dominica

If you’ve arrived in Saint Lucia by plane, head to the city of Castries and take a ferry boat to Fort-de-France, Martinique. Once you’ve explored this beautiful French overseas territory, take another ferry ride from Fort-de-France to Pointe a Pitre, Guadeloupe . Once you’re ready to leave Guadeloupe, you can either take one of various ferries to the smaller islands of Guadeloupe, or head to the country of Dominica.

Ferry Boats for Island Hopping in the Caribbean

Ferries make it incredibly easy and economical to island hop in the Caribbean. Click here to see all available ferries in the Caribbean islands.

Unfortunately, not all Caribbean islands are connected by ferry boat or flight, but as each year passes, more and more means of transportation are being added.

Let us help you make your Caribbean island hopping experience the best it can be! Find incredible Caribbean villas here.

Main image source: FRS Caribbean

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A Journey of Paradise: The Ultimate Guide to Island Hopping in the Caribbean

Introduction: island hopping in the caribbean.

Table of Contents

The allure of the Caribbean

The Caribbean, with its turquoise waters, pristine beaches, and vibrant cultures, has long been a dream destination for travelers seeking a tropical paradise. Each island in the Caribbean boasts its own unique charm, from lush rainforests and hidden coves to lively festivals and mouthwatering cuisines.

Discover the hidden gems of island hopping

While popular destinations like the Bahamas and Jamaica are well-known, the true magic of the Caribbean lies in its lesser-explored islands. Island hopping allows you to uncover these hidden gems and immerse yourself in the authentic Caribbean experience, filled with adventure, relaxation, and cultural wonders.

Choosing Your Caribbean Adventure: Island Hopping in the Caribbean

Exploring the diverse caribbean islands.

The Caribbean archipelago comprises more than 7,000 islands, each with its own distinct character. From the Eastern Caribbean’s lush landscapes to the Western Caribbean’s pristine reefs and the Southern Caribbean’s tranquil havens, there’s an island to suit every traveler’s preferences.

Popular vs. off-the-beaten-path destinations

While some islands attract throngs of tourists, others remain relatively untouched and offer a sense of seclusion and tranquility. Consider whether you prefer the bustling energy of popular hotspots or the serenity of lesser-known destinations.

Factors to consider when planning your trip

When planning your island-hopping adventure, take into account factors such as the best time to visit, visa requirements, transportation options between islands, and the experiences you wish to prioritize.

Essential Tips for Island Hopping in the Caribbean

Understanding transportation options.

Learn about the various transportation modes available for island hopping, including ferries, small planes, and charter boats. Each option offers a different experience and level of flexibility.

Packing wisely for your Caribbean adventure

Pack light, breathable clothing, swimwear, and sun protection essentials. Don’t forget insect repellent and a reusable water bottle to stay hydrated.

Safety precautions to ensure a worry-free experience

Prioritize safety during your journey by staying informed about weather conditions, respecting local customs, and carrying a basic first-aid kit.

The Eastern Caribbean Odyssey: Island Hopping in the Caribbean

Discovering the british virgin islands.

Explore the stunning beaches and vibrant marine life of the British Virgin Islands. Visit the Baths at Virgin Gorda and indulge in world-class sailing.

Exploring the vibrant cultures of St. Kitts and Nevis

Experience the rich history and cultural heritage of St. Kitts and Nevis, known for their historic landmarks and friendly locals.

Uncovering the natural wonders of Dominica

Discover Dominica’s lush rainforests, waterfalls, and hot springs, earning it the title “Nature Island” of the Caribbean.

Experiencing the enchantment of Barbados

Immerse yourself in the lively atmosphere of Barbados, known for its vibrant festivals, flavorful cuisine, and beautiful beaches.

The Western Caribbean Expedition

Unraveling the charm of the cayman islands.

Encounter stunning coral reefs and the famous Stingray City in the Cayman Islands, a diver’s paradise.

Venturing into the untouched beauty of Belize

Embark on an eco-adventure in Belize, home to the Belize Barrier Reef, ancient Mayan ruins, and lush jungles.

Embracing the rhythms of Jamaica

Feel the rhythm of reggae in Jamaica and indulge in its rich cultural heritage, warm hospitality, and breathtaking waterfalls.

Immerse yourself in the vibrancy of Cuba

Experience Cuba’s colorful architecture, lively music, and fascinating history as you explore its charming cities.

The Southern Caribbean Escape

Splendor and serenity in aruba.

Relax on Aruba’s white sandy beaches, indulge in water sports, and savor the island’s laid-back vibe.

Discovering the rich history of Curacao

Uncover the Dutch colonial charm of Curacao, with its vibrant architecture and lively cultural scene.

Unveiling the paradise of Grenada

Explore Grenada’s spice plantations, lush rainforests, and stunning beaches, earning it the nickname “Spice Isle.”

Hidden treasures of Trinidad and Tobago

Immerse yourself in the vibrant culture and natural wonders of Trinidad and Tobago, known for their lively festivals and diverse landscapes.

Island Hopping in the Caribbean Itineraries

One week in paradise: ideal itinerary for first-timers.

Experience the best of the Caribbean in one week, combining a mix of relaxation, exploration, and adventure.

Extended adventures: Suggestions for long-term explorers

For travelers with more time, create an extended island-hopping itinerary that allows for deeper exploration of multiple islands.

Off-the-grid escapes: Exploring lesser-known islands

Embark on a journey to lesser-known islands, offering a sense of seclusion and authenticity for intrepid explorers.

Experiencing the Caribbean Culture

Indulging in local cuisine and culinary delights.

Sample the flavors of the Caribbean, from jerk chicken in Jamaica to conch fritters in the Bahamas.

Discovering the unique arts and crafts of the region

Explore the vibrant art scenes of various islands, from colorful murals to handcrafted souvenirs.

Celebrating vibrant festivals and local traditions

Time your visit to coincide with lively festivals and events, such as Carnival celebrations and reggae festivals.

Unparalleled Caribbean Adventure Activities

Diving into the depths: exploring the coral reefs.

Dive or snorkel in the crystal-clear waters of the Caribbean to witness diverse marine life and vibrant coral reefs.

Trekking through lush rainforests and hiking trails

Embark on hiking trails and nature walks to encounter the Caribbean’s rich biodiversity and stunning vistas.

Engaging in water sports and adrenaline-pumping activities

Try your hand at various water sports, such as windsurfing, kitesurfing, and paddleboarding, for an adrenaline-filled adventure.

The Best Time to Island Hop in the Caribbean

Understanding the climate and weather patterns.

Learn about the Caribbean’s climate and seasonal variations to plan your visit during the most favorable conditions.

Making the most of the off-peak tourist seasons

Consider traveling during the off-peak season to enjoy quieter beaches and potential discounts on accommodations and activities.

Special events and festivals to consider

If you have specific festivals or events in mind, check their dates and plan your island-hopping adventure accordingly.

Planning Your Island Hopping Budget

Accommodation options for every budget.

Explore a range of accommodation options, from luxury resorts to budget-friendly guesthouses and hostels.

Transportation costs and money-saving tips

Plan your transportation budget wisely, and consider purchasing island-hopping passes for cost-efficient travel.

Dining and entertainment expenses to consider

Factor in dining and entertainment costs to savor the best culinary experiences and immerse yourself in local culture.

Essential Island Hopping Dos and Don’ts

Respecting local customs and cultural etiquette.

Be mindful of local customs and traditions, such as appropriate dress codes and respectful behavior.

Being mindful of environmental conservation

Support eco-friendly initiatives and preserve the Caribbean’s natural beauty for generations to come.

Staying safe during your Caribbean adventures

Prioritize safety during your island-hopping journey, whether on land or at sea, and stay informed about potential risks and precautions.

Summary: Embark on a Caribbean Paradise

Recap of the breathtaking islands covered.

Summarize the diverse Caribbean islands and experiences showcased throughout the article.

Highlights of the unique experiences awaiting you

Remind readers of the enchanting experiences and cultural wonders that await them on their Caribbean island-hopping adventure.

Encouragement for readers to begin their island hopping journey

Inspire readers to pack their bags and embark on an unforgettable Caribbean paradise expedition.

FAQs (Frequently Asked Questions)

What are the must-visit caribbean islands for first-time visitors.

Discover the top Caribbean islands that offer a perfect blend of stunning beaches, rich culture, and vibrant activities for first-time visitors.

How can I get around the Caribbean islands efficiently?

Learn about the transportation options available for island hopping in the Caribbean, including ferries, local airlines, and charter boats.

What are the visa requirements for traveling to the Caribbean?

Find out about visa requirements for different Caribbean destinations and tips for smooth travel documentation.

Is island hopping suitable for families with children?

Explore family-friendly Caribbean islands and activities that cater to travelers of all ages.

What is the best time of the year to go on a Caribbean island hopping adventure?

Consider the ideal time to visit the Caribbean based on weather, seasonal events, and tourist crowds.

Are Caribbean island cruises accessible for individuals with mobility restrictions?

Discover the accessibility options and considerations for travelers with mobility challenges on Caribbean cruises.

What kind of onboard amenities can I expect on a Caribbean island cruise ship?

Learn about the facilities, dining options, and entertainment offered on cruise ships exploring the Caribbean islands.

What should I pack for a Caribbean island hopping adventure?

Get packing tips for your Caribbean journey, taking into account the tropical climate and various activities.

How far in advance should I book a Caribbean island cruise?

Understand the best time to book your Caribbean island cruise to secure the best deals and cabin availability.

Are gratuities included in the price of a Caribbean island cruise?

Find out about the cruise lines’ gratuity policies and whether tips are included in the cruise fare.

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Island Hopping The Caribbean—How To + Itinerary Ideas

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This guide to Caribbean island hopping is authored by Leo (with some additions by me, Nina!)

Island hopping in the Caribbean is a great way to visit numerous places in one area on the same vacation. The best part is that Caribbean island hopping is pretty easy to do yourself, so you can forget about sharing space with hundreds (or even thousands) of other people on a giant cruise ship – unless that floats your boat!

There are endless activities, cultures, and coastal vibes to choose from when you go island hopping in the Caribbean. Because this chain of islands sits so close together, it’s the perfect place to pack a lot into a short trip.

The Caribbean lifestyle is ideal if you’re looking for a unique vacation. It has everything from golden pristine beaches and water activities to barefoot restaurants and rum stores, and there are a lot of different itineraries you can choose from.

From budget options to luxurious getaways, relaxing beach trips, and more adventurous escapades, the Caribbean will not disappoint!

Below, we’ve put together a few ideas for a Caribbean island-hopping journey, how to hop from island to island, and some insider tips to make your trip a breeze.

Table of Contents

Public Ferries

Cruise ships, charter or rent a private yacht or boat, harbour island, st. martin/saint maarten, and even further:, resources for your trip:, the british virgin islands, antigua and barbuda, the u.s. virgin islands, caribbean island-hopping travel guide #4: turks and caicos, caribbean island-hopping travel guide #5: montego bay, jamaica, check your visas, when to go island hopping in the caribbean, set up a base, don’t rush, compare quotes, safety first, 15 best beaches in turks and caicos and where to stay nearby, 17+ things to do in turks and caicos for the adventurous, things to do in jamaica: a 2-week itinerary, best things to do in guadeloupe on an adventurous 4 days itinerary, a mini guide to anguilla: things to do, beaches, & more, 5 incredible anguilla resorts and villas to stay in, adventurous things to do in antigua and barbuda + tips, 8 things to do in dominica and how this trip changed my life, how to get around while island hopping the caribbean.

Whether you’re on a backpacker’s budget or hoping to go all out while island hopping the Caribbean, there are a few different ways to get from point A to B.

Many conjure images of massive cruise ships or opulent yachts when they think about island hopping in the Caribbean. While these are both viable options (more info on both below), one of the lesser-known ways to get around this archipelago is via public ferry.

While this may not be the greatest option if you are hoping to travel long distances in a short amount of time, if you are simply hoping to hop over to the nearest island, public ferries are a great way to go. The best part is that the ferries are extremely affordable!

There are many options for traveling via public ferry across the Caribbean, with services available in the Bahamas, various British, French, and Dutch overseas territories, St. Lucia, the Virgin Island, and more!

Note that while services on some islands are extensive, other islands have no ferry service at all. You may need to do a little research in advance if you plan on island hopping via public ferry, but the bucks you’ll save make this option worth it!

Cruises are one of the most tried and true methods of island hopping in the Caribbean. If you want to sit back and relax without worrying about how to get to your next destination, then taking a cruise is a great option. There are many options at various price points, so finding an itinerary that suits your travel needs should be no problem.

If money is no object, you can charter or rent a private boat or yacht for your island hopping extravaganza. Options are endless for sailing around the Caribbean, whether you want to do it yourself or hire someone else to take the wheel.

Another way to bop around while island hopping in the Caribbean is by taking flights between islands. While it’s a cheap and fast approach to Caribbean island hopping, flying should only be done as a last resort or if the distance you are traveling is significant.

While it may seem like the best way to go since it’s so speedy (some flights are only 15 minutes of actual flight time!), the small planes traveling between islands can be downright terrifying. And anyway, who wants to spend their island getaway stuck in airport security lines?

Caribbean Island-Hopping Travel Guide #1: The Bahamas

When daydreaming about a Caribbean getaway, many picture the Bahamas. This chain of islands has all the quintessential attributes you imagine when you think of a vacation in these parts. The islands comprise more than 700 beautiful subtropical islands and many smaller islands called cays.

You can start your trip in Nassau, just 184 miles from Miami, Florida. This thriving country’s capital hub has a good mix of city and island life and many Bahamian traditions and culture.

You can stay in New Providence for a night or two or head over to Paradise Island – home to Atlantis’ gigantic and vast water park.

Even if you don’t stay on Paradise Island, check out Cabbage Beach. You’ll have to pay a small fee to cross the bridge onto the island, but the beach is good enough to justify the minuscule price. This is among the world’s best-known beaches for a good reason.

Visitors can also visit Blue Lagoon Island, which is officially called Salt Cay. It is a beautiful private island with a calm lagoon, great beaches, and lots of water and land-based activities for the whole family to appreciate.

The island is only three miles from Nassau and is easy to get to by boat from Nassau’s historic harbor. It has everything you would expect from a tropical island, like swaying palm trees, white-sand beaches, crystal clear water, verdant natural vegetation, vibrant tropical birds, and colorful coral reefs.

Here you can enjoy snorkeling, scuba diving, water skiing, fishing, and sailing. Blue Lagoon Island is also a sanctuary for the dolphins and sea lions of Dolphin Encounters, where tourists can socialize with dolphins and sea lions in their natural ocean habitat.

→ Book a parasail adventure over Cabbage Beach.

After visiting Nassau, you can catch a morning ferry to Harbour Island. Here you’ll find small island allure and lengthy strips of soft pink sand. There are several fantastic boutique hotels in this area that are very close to the beach, and they’re all excellent.

You will probably spend most of your time at Pink Sands Beach swimming and lying in the sun. It’s heaven on earth. While it would be easy to laze on these scenic sands indefinitely, be sure to walk along the coast, where you can find many other cute boutique hotels, diners, and jaw-dropping homes.

Visitors can also roam through the quiet streets, searching for pastel-colored cottages and unique architecture while having fun with the occasional chickens wandering around.

Next up on your Caribbean island hopping tour is Eleuthera. Harbour Island lies just outside this much larger island, so Eleuthera is a great next stop.

Eleuthera is known as the pineapple center of the world, and residents say that the Gregory Town pineapple is the sweetest on the planet. It is thought that the Bahamas was the first nation to grow the fruit.

While here, visit the Glass Window Bridge – your Instagram feed will thank you! This small bridge connects the rough Atlantic Ocean with the serene waters of the Bight of Eleuthera and seeing them side by side is quite stunning.

You can end your trip back to Nassau or venture to more remote parts of the Bahamas. The Exuma Islands is an excellent option for a more far-flung adventure, and you can get here via ferry or chartered plane.

The Exumas have 365 islands, and they’re known for their swimming pigs , nurse sharks, and other marine life. There are also boating adventures, on-island trips, and miles of hardly ever visited beaches to keep you entertained for days.

Caribbean Island-Hopping Travel Guide #2: The French Caribbean islands

Also known as the French West Indies, the French Caribbean islands boast quintessential island vibes, each with its own flare.

When you get to St. Martin, you’ll be in the middle of a split island between France and the Netherlands. Many choose to stay on the French side because of its intimate restaurants, absolutely adorable shops, and pristine beaches.

On the other hand, the Dutch half of the island is renowned as the party side.

However, even though a lot is going on, St. Martin and St. Maarten still have a stress-free vibe, starting with how easy it is for you to get from one end of the island to the other.

So start your day with a few rays on a quiet Dutch beach. Then, wander down a French-side mountain in the afternoon. Afterward, you’ll be more than ready to sneak back to the border for a night at the casinos.

A quick 15-minute flight will take you to St. Barts, where you’ll land on one of the shortest landing strips in commercial aircraft. You can also take a 45-minute ferry ride from St. Martin instead, which might be preferred for some.

St. Barts (or St. Barths, as the natives call it) is where you can enjoy laid-back luxury and a French touch. This is popular on Caribbean island hopping itineraries because of its delightful tropical weather and numerous idyllic beaches. There are 16 beaches on the island, each with its unique personality.

There are also many chic boutiques and diners. In other words, be prepared to spend a tad more on this portion of the journey.

Guadeloupe is comprised of 12 French islands, featuring lots of deserted beaches and forested hiking trails. Bridges connect Basse-Terre and Grande-Terre (Guadeloupe’s two largest islands), which look like a butterfly from the sky.

Guadeloupe’s mix of extraordinary greenery magnificence and wealthy Creole and French traditions makes it an enchanting place to visit. The archipelago is part of France, and the cuisine, language, and heritage of Guadeloupe show that there is a strong connection.

La Desirade, Les Saintes (also known as Îles des Saintes), and Marie-Galante are three smaller islands of Guadeloupe. All three have beautiful beaches and small, charming towns.

Guadeloupe’s islands are great places to go birdwatching, take photos, hike, and do water sports like scuba diving, swimming, and snorkeling. (If you go on any of these activities, don’t forget to bring an action camera or go pro to capture unforgettable moments!)

Guadeloupe also has a lot of fun carnivals and festivals, like the five-day Mardi-Gras Carnival that ends on Ash Wednesday.

Depending on how long you have, from Guadeloupe, you can get to other islands like Martinique, St. Lucia , Antigua , and even St. Kitts beaches by taking one-way flights from LIAT and Caribbean Airlines.

RELATED: Best Things to Do in Guadeloupe On An Adventurous 4 Days Itinerary

Although it’s now a sovereign state, St. Lucia was colonized by the French and retains some of the culture to this day. Add St. Lucia to your Caribbean island-hopping itinerary, and you won’t be sorry.

This island boasts all the classic Caribbean flare, with gorgeous beaches and bright blue waters. But it also has some unique things to offer visits, including two massive mountain peaks that make the island’s topography unlike anywhere else in the Caribbean.

Thanks to these two towering peaks (called pitons), there are plenty of adventurous things to do in St. Lucia . The true daredevils can attempt to ascend both peaks (warning – this is not for the faint of heart), while more realistic adventurers can hike a nearby trail for some epic views.

You could also visit Sulphur Springs Park to enjoy a mud bath and then check out the geothermal activity of the active volcano nearby.

Those who want a mix of adventure and history can explore the trails in Pigeon Island National Park and Fort Rodney. There are excellent views of the coast and some cool information about the remains of the military fort.

Food and Culture

For a hefty dose of both food and culture, don’t miss the Gros Islet Street Party! Both locals and tourists turn out en masse to enjoy rum, street food, and the vibrant Caribbean ambiance every Friday night on the island’s northern tip.

For a more relaxing meal, check out the Jambe de Bois Restuarant for some delicious local grub.

St. Lucia also has its fair share of scenic beaches. The locals love Soufriere Beach, with its uncrowded shores and incredible views of the pitons.

Sugar Beach is perhaps the most famous beach in all of St. Lucia. If you’re looking for a scenic spot to kick it for the afternoon, you’d be hard-pressed to find a better stretch of sand. You can also snorkel right off the beach!

If you’re searching for a more secluded spot to spend the day, check out Anse Chastanet or the beaches around Pigeon Island National Park.

READ MORE: 15 Things To Do in St. Lucia—Best Beaches and Adventures!

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Caribbean Island-Hopping Travel Guide #3: The Virgin Islands

The British Virgin Islands and U.S. Virgin Islands are among the best spots to sail in the Caribbean, thanks to trade wind gusts, crystal-clear blue water, and sophisticated coral reef structures. Whether you’re taking advantage of the winds, there’s plenty to see and do along this Caribbean island chain.

Both the British and the U.S. Virgin Islands have a lot of natural beauty and a combination of old-world elegance and luxury resorts that make them very appealing.

Virgin Gorda (the biggest island in the British Virgin Islands) and Jost Van Dyke (a beach party island) are both must-sees while island hopping in the Caribbean.

There is a beautiful beach on Virgin Gorda called The Baths. Here visitors can take a dip, snorkel, and experience the world until they get hungry. Nearby Jost Van Dyke is where you’ll find the best nightclubs and musical performances you’ll see all along your trip.

Between these two main islands are many other interesting ones, like Norman Island, Salt Island, and Cooper Island, to mention a few. Their appeal comes down to a few simple things: miles of beautiful, clean sand beaches, dive sites unlike anywhere else, and a gentle breeze that blows all the time.

You should also make Tortola one of your Caribbean island-hopping stops. Tortola is an island that is a British Virgin Island full of color. That doesn’t just mean the evergreen forest at higher elevations; it also implies the houses, flowers, food, and even the clothes.

The beaches on the northern shore of Tortola are the best. Snorkelers and divers will enjoy the rich sea life, hikers will enjoy the national parks and botanical gardens, and art enthusiasts will be amazed by the vibrantly colored street art and painters’ studios .

There are also many cafes, bars, stores, and food outlets in the marina in Tortola.

→ Book a private art and culture tour in Tortola.

If you have some extra time in the British Virgin Islands, hop over to the nearby Antigua and Barbuda . While these islands have been independent since the 1980s, they were once ruled by Great Britain and retain many of its traditions.

Like most of the neighboring islands, there’s plenty of relaxing to do here. For those who want a little more action out of their Caribbean island-hopping excursion, there are also tons of adventurous things to do in Antigua and Barbuda .

READ MORE: Adventurous Things to Do in Antigua and Barbuda + Tips

Known as the gateway to the U.S. Virgin Islands, St. Thomas is a great spot to kick off your Caribbean island hopping adventure. The island is known for its epic beaches, snorkeling spots, and historic watchtower and fort. There’s a little something for everyone on St. Thomas!

Although the smallest of the three U.S. Virgin Islands, St. John packs a big punch. St. John’s Virgin Islands National Park covers almost the whole island, with a lot of beautiful scenery. You can hike trails through old plantations, visit one of the many serene beaches, or snorkel the sheltered bays .

The famous Trunk Bay is home to the Coral Reef Underwater Park Trail, where snorkelers will find underwater signs that depict the types of fish and other sea creatures you might see. In addition to the national park, St. John’s has plenty of lovely shops for gifts and high-end restaurants.

The U.S. Virgin Islands and the British Virgin Islands are relatively close to each other compared to other island vacation spots, with transit times often less than one hour.

RELATED: Best Places to Visit in the Dominican Republic

The Turks and Caicos Islands are a group of islands comprised of eight main islands and many smaller islands called cays. Each island is indeed unique in its way, and each can be a tourist attraction in itself.

Even though you might be interested in different things, island hopping the Turks and Caicos Islands will be an experience that you’ll never forget. Your idea of a good time will help you decide where to visit the Turks and Caicos.

While it is known for its scenic white sand beaches, there are plenty of adrenaline-inducing activities to experience in Turks and Caicos as well. You can jet s ki out to an old shipwreck, kayak through stunning cays around Providenciales, or explore caves in Middle Caicos.

Because the Turks and Caicos Islands are at the crossroads of year-round trade winds, they are a popular spot to go kiteboarding. Long Bay Beach on Providenciales is a great place to do the sport because of the shallow waters and reliable conditions.

There are also tons of great diving spots on all the islands, but some of the best can be found on Provo, Grand Turk, and Salt Cay.

History buffs might be keener on the Middle Caicos island, where you can see the old plantations and salt flats.

→ Book a private kiteboarding lesson on Long Bay Beach.

There are plenty of places to get your weight’s worth in fresh seafood around Turks and Caicos, but perhaps the best is the Thursday Fish Fry.

You’ll find grilled lobster, conch, and other seafood served up fresh from some of the island’s best restaurants in a casual setting at Stubbs Diamond Plaza every Thursday night. There are also stands selling homemade trinkets, a band, and plenty of opportunities for dancing and people-watching.

→ Book a Turks and Caicos food tour .

Make sure you set aside some time for some seriously white sand when you’re island hopping in the Caribbean. Providenciales Island (Provo) is home to Grace Bay Beach , voted one of the best beaches in the world.

There are miles and miles of beaches in Turks and Caicos. Most gently slope into some of the most beautiful blue waters you’ve ever seen, making this island chain one of the best for swimming. You might not know what genuine turquoise looks like until you’ve been here!

Turks and Caicos also have some of the most luxurious all-inclusive resorts in the Caribbean, perfect for planning your dream holiday!

READ MORE: 17+ Things To Do in Turks and Caicos Clear Kayaking to Iguana Island in Turks and Caicos Where to Stay in Turks and Caicos : 13 Resorts and Hotels 15 Best Beaches in Turks and Caicos

As the third-largest city in Jamaica, Montego Bay has many things to do and see for everyone.

Visitors can go on a spectacular eco-adventure with Cockpit Country Adventure Tours. You’ll voyage through breathtaking caverns glistening with marvelous geographical treasures that were once a secret base for Maroon warriors.

You could also take the whole family or group of friends to Paintball Jamaica for a fun-filled day of play in a secluded area with many trees and lots of shade.

Jamaica’s only natural nighttime attraction is its bioluminescent bay, which you can see by going to the Glistening Waters Hotel before sundown and taking a tour of the Luminous Lagoon . The tour boats leave the hotel and go to a quiet part of the lagoon where tiny sea creatures light up when moved.

It’s cool to watch the effect when the boat travels through the water, but it’s even cooler to jump in and see how moving your hands and feet makes glowing swirls and eddies.

Another one of the best things to do in Montego Bay is to enjoy the Martha Brae River. You can do so by taking a bamboo raft down the river, surrounded by greenery and the sound of the wind, flowing streams, and birds chirping.

→ Book a Martha Brae River bamboo rafting adventure .

Visit Sam Sharpe Square, a local hangout with a cobblestone plaza and historical landmarks. This is the site of the Montego Bay Cultural Center, where you can go to learn about the unique town’s history. You can also learn about Sam Sharpe Square and what it means to locals.

If you’re a fan of Usain Bolt, check out his sports bar and do your “to di world” pose right in front of the statue of the fastest man on earth.

There are a lot of restaurants in this city. It’s an excellent place for a foodie who wants to try some of the best food in Jamaica.

Pro tip: Talk to your local tour guide about their favorite place to eat so you can try some of the best home-cooked food with authentic Jamaican flavor.

→ Book a private Jamaican food tasting tour.

You’ll also discover a variety of both exciting and relaxing beaches in Montego Bay. In addition, most beaches have diners serving Jamaican food to keep you fueled through the day.

Doctor’s Cave Beach is right on the “Hip Strip,” which is excellent for families. You can get a great tan here because the beach is expansive, with only a few palm trees to shade you. There are lounge chairs with umbrellas for those wanting a break from the sun.

Aqua-Sol Theme Park has a lot of fun things to do right on the beach with go-karts, water slides, and entertainment for the whole family to keep everyone happy.

Another beach near the city is the 876 Beach Club. The party is always going on at this place, with live music and entertainment, a vast floating water park for endless fun, a sizzling jerk pan for lunch and snacks, a filled bar, and well-kept grounds.

If you want to stay in Montego Bay, you will find some luxury options here. You can stay at one of the best Sandals resorts called Royal Caribbean.

RELATED: Things to Do in Jamaica: A 2-Week Itinerary

Tips for Island-Hopping in the Caribbean

There are a few things to remember when planning a Caribbean island-hopping trip.

You should check to see if the islands you want to visit are all in the same country. If not, you’ll need visas for every one of them. For most Americans and Europeans, visas are not required for stays shorter than 90 days, but it’s always good to double-check before you arrive.

You should also check the entry restrictions for each country you visit. While COVID restrictions have largely been lifted in the Caribbean, each island has the right to require negative tests and/or proof of vaccine.

While the islands of the Caribbean are renowned for their year-round tropical weather, some seasons are better for visiting than others. December through April are the best for balmy temperatures and little rain.

However, this is no secret, and many tourists flock to the islands during this time to escape the cold winter weather back at home.

You should also look out for hurricane season (July through November) and plan to avoid this time if possible. For the best mix of good weather and sparse crowds, plan your Caribbean island hopping vacation for a shoulder season, either May or October.

Be ready to pack light. If you’re traveling by plane, you can save time by only taking a carry-on bag with you. Similarly, if you’re on a ferry, it’s not fun to be weighed down with luggage.

That being said, don’t pack too light. While the weather is generally warm during the day, it can cool down at night. You may want to have at least one light jacket and a pair of pants along with you, no matter the season.

RELATED: The Essential Beach Packing List (+ Fun Items and Tips!)

For people who don’t like leaving home for more than one or two days with only what they can fit in a carry-on bag, think about using one island as a starting point for your trip.

You can book a hotel or villa for the whole trip, and then go on day trips or overnight trips to other islands while leaving your belongings.

When you plan your Caribbean island-hopping trip, stay at least two nights in every place. You’ll miss the entire point if you try to cross off as many places and Instagram posts as possible. The goal of a Caribbean vacation is to have fun and relax!

When you get a price estimate for a tour or private transfer, it’s worth it to call around and get a few more prices. Don’t forget to ask about additional dock fees, airport costs, and taking off fees.

In general, the Caribbean is a highly safe vacation destination. However, there are a few things that every traveler should keep in mind.

Many flights between islands could be done in a small plane, such as a prop plane. Ask about safety when you ride in a prop plane. Any reputable and reliable operator should have safety information on hand and be willing to answer questions about their pilots.

While most are famed for their idyllic disposition, there are some Caribbean beaches that experience rip tides and rowdy waves. Always keep an eye out for flags posted, and don’t swim out too far if the currents are strong.

Petty theft is also a thing to be aware of while island hopping in the Caribbean. Don’t leave valuable belongings alone on the beach or in the rental car!

There’s a lot more to island hopping in the Caribbean but we hope this guide helped you plan a bit better!

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My name is Leandro (Leo for short). I am a digital marketer who one day discovered that I love blogging, SEO, and ways to make money online. Traveling and exploring cultures is another of my passions.

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Island Hopping the Caribbean – 13 AMAZING Islands

After six months spent in West and Central Africa, we were ready for some sun, beach and some visa-free countries.

Naturally, island hopping the Caribbean seemed like the perfect idea.

Hi, we’re Rach & Marty!

We’ve visited every country in the world and want to help you get the most out of your travels!

Whether you need an expertly planned itinerary , some experienced hints and tips , or just craving a delicious food adventure , we’ve got you covered!

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Over 7,000 islands surrounded by turquoise waters and home to pristine white beaches just waiting to be discovered – yes, please.

It was a perfect time as well. March and April are great months to go, it is the end of the high season, so the weather is still nice but you will most likely find an empty beach too.

The Caribbean is a unique part of the world where most of the visitors come on pre-arranged packages, resort stays and of course as part of the ever-expanding cruising industry. Independent travellers keen on island hopping are quite rare.

As expected, the islands do cater mostly for cruisers and resort stayers.

But with a bit of planning and knowledge, island-hopping across all 13 independent countries is possible. And if you are lucky you might visit a few islands that despite being overseas territories, they’re also worth visiting.

But most importantly, some islands offer much more than just a beach.

In this article, we provide some information on our experience in the Caribbean in April 2019 and ALL updated information on airlines and ferries in 2024..

Table of Contents

How many countries are there in the Caribbean?

There are 13 sovereign countries in the Caribbean, and it is possible to visit them all in just one longer trip.

Antigua and Barbuda

The bahamas, dominican republic, saint kitts and nevis, saint lucia, saint vincent and the grenadines, trinidad and tobago.

Additionally, these are the overseas territories in the Caribean:

• British overseas territory: Anguilla, British Virgin Islands (Tortola, Virgin Gorda, Anegada, Jost Van Dyke), Cayman Islands, Montserrat, Turks and Caicos Islands
• France overseas territories:  Guadeloupe, Martinique, Saint Barthélemy, Saint Martin
• USA overseas territories:  Puerto Rico, United States Virgin Islands (Saint Croix, Saint John, Saint Thomas)
• Overseas territories of the Netherlands: Bonaire, Sint Eustatius, Saba, Aruba, Curaçao, Sint Maarten

By the way, did you know the Caribbean is part of the North American continent? Find out more about it here:  How Many Countries in North America? Why 3 is The Wrong Answer!

How to plan your island-hopping Caribbean itinerary?

Getting to the Caribbean is not particularly hard, there are plenty of direct flights from Europe and North America to get you there. If you are travelling on a budget, the best option is to search for European charter flights to Barbados, Guadeloupe, or Martinique and start your travels from there.

We use Skyscanner  to book the best deals on flights anywhere in the world and great to create the most cost-effective Caribbean island-hopping itinerary.

Are you coming from Canada or the USA? Well, you are spoilt for choices of flights and can possibly do your Caribbean Island hopping in a few segments. If you are aiming to visit all of them, a good idea might be to start in the south (ie Trinidad or Barbados ) and hop your way north.

Or start in the Bahamas and make your way south. 

I know  how to find and book cheap flights  and I can also help you choose the right luggage: Backpack Vs Suitcase – which one should you choose? 

Island hopping the Caribbean as an independent traveller – What is it really like?

I admit it, island hopping the Caribbean can be lonely at times. It’s harder to meet other travellers and hopping from island to island can be costly as there are simply no cheap flights (minimum of $100-$150).

There are not that many ferries (mostly in the Eastern Caribbean) and you could possibly help out on a boat to catch a ride to the next island but that does require more time and waiting around.

Island hopping the Caribbean – Ferry vs Flights vs Cruise

Cruises around the caribbean.

I am personally not a big fan of cruises. You have limited time on each island, the whole concept of cruise enriches the people who own them and little goes to the actual islands. It’s also very bad for the environment.

Locals in the Bahamas said to me that according to the statistics, cruise visitors only spent 10 USD on the island, as they eat and drink on the cruise ship and organise trips through the cruise as well.

But I know many people are simply short on time, and cruises can offer fantastic value.

For those with a fear of flying, this can be the perfect option to visit the Caribbean. If you do choose to book a Caribbean Cruise , try to contribute to the local economy, rather than booking excursions from the cruise company.

Make sure you get Travel Insurance before hitting the road. We recommend Heymondo & SafetyWing Travel Insurance.

Click here and get 5% off Heymondo from us!

How to fly around the Caribbean?

There are two options here. You can either fly in and out of most of the islands from Miami . Or you can connect them with small Caribbean Airlines, but this requires some planning as flights are not daily and a few were cancelled during the pandemic.

Here are a few airlines to look at, and again, the best way to search for prices is on Skyscanner .

InterCaribbean Airways , Ltd. is a passenger airline based in the Turks and Caicos Islands  flying to Antigua, The Bahamas, The British Virgin Islands, Cuba, Dominica, Dominican Republic, Haiti, Jamaica, Puerto Rico, St. Lucia, Barbados, Grenada, St. Vincent and the Grenadines, and St. Maarten. You can find the current schedule here.

LIAT (Leeward Islands Air Transport) has its headquarters in Antigua,  and it is the best airline to use for island-hopping the Caribbean as it connects many islands.

We used LIAT the most. Click here for the current flight schedule with LIAT .

Caribbean Airlines – The Trinidad Tobago-based carrier flies to 14 island destinations St. Maarten, Antigua, St. Lucia, St. Vincent , and Nassau, Bahamas to name a few.

Air Caraibes  based on the French island Guadeloupe, mainly services the French Caribbean islands: St. Barts, Martinique, and 14 other island airports across the region.

Cayman Airways  flies from all three Cayman Islands to Cuba (Havana) and Jamaica (Kingston and Montego Bay) . Click here for the current flight schedule for Cayman Airways .

Bahamas Air  is based in Nassau Bahamas and connects several cities in Florida , but also connects  Turks and Caicos, Havana, Kingston, and Santo Domingo, Dominican Republic.

Caribbean Ferry between 4 Islands

If you plan to island-hop the Caribbean with ferries, I have bad news. These are not really the Greek islands, and a majority of the Caribbean islands don’t have standard passenger ferries.

I mean, there are small ferries, like in St Vincent and the Grenadines where you can take a ferry to the next islands, but when it comes to international crossing, there aren’t many.

There is one ferry that connects 4 different islands:  L’Express des Iles (translates to the express of the Islands).

L’Express des Iles offers a dependable, inexpensive, and pleasant ferry service between the islands of Martinique, Guadeloupe, Dominica, and St.Lucia (and Marie Galante and Les Saintes). You can book your ticket online easily and see the cost and schedule. The website is in French only, however. 

Our Island Hopping the Caribbean in 2019:

To give you a better insight, here is a little recap of each island. Yes, things have changed since the pandemic, but the cost or vibe of these islands will be the same. Our island-hopping Caribbean itinerary started in Barbados and finished in Haiti .

Our island hopping started in Barbados, and we really liked it here. We spent almost a week here and found the island big enough to entertain ourselves.

The beaches are beautiful with white sand, and despite the package holidaymakers, you can still find your private spot like on the Miami beach.

Bridgetown, the capital, didn’t seem to win us over at all. Yes, we admit it is expensive to eat or drink out, but we only went to Oistins for the fish market to treat ourselves and otherwise, we found enough local eats to get by. In some way, we also had a fantastic stay due to our Airbnb host.

Find more details about our accommodation in our blog post How to visit Barbados on a Budget .

Trinidad & Tobago is known for its festival, but we were too late for the party. Instead, we were keen to try some of its food, which is quite unique in the Caribbean due to the influence of Indian immigrants.

We tried doubles, roti filled with Indian curries, plus bake and shark, too. If you head to the north side, you’ll find the nicest beach at Maracas Bay.

Or you can check out the many waterfalls inland – Maracas Waterfall was our favourite.

Oh, Grenada, you had us at your views of the harbour. We arrived in the middle of the night and woke up to stunning views of St George, the capital of Grenada .

We went exploring the town and did a food tour to learn and taste some of the food on the island.

Grand Anse beach is where you want to go. A beautiful white sand beach with crystal clear waters and lined with almond trees. This is an island we would definitely like to return to.

Here are our top  10 things you shouldn’t miss in Grenada.

We considered travelling to St Vincent on a boat from Grenada, but it would take a few islands to hop and a few ferries/boats. But if you have time, this is an excellent option as you would get to see a few other islands, such as Carriacou and Union Island.

We arrived in St Vincent and took the public bus to the top of the green hills where we stayed in our Airbnb. Everyone told us we must go to Bequia island which is accessible by daily ferry. We were promised some of the best beaches in the Caribbean and the island really delivered.

This island was gorgeous, and there are a bunch of amazing things to do here .

We were all beached out when we arrived in Saint Lucia , so we decided to stay close to Gros Islet and Rodney Bay. Our Airbnb place was super cosy and gave us a chance to catch up on some blogging and planning the upcoming island hopping.

We knew St Lucia was a popular stop for yachties, and walking around the harbour we could see why it’s beautiful here. 

Gros Islet is known for its Friday street party; we ended up walking the colourful streets mid-week as we were leaving on Friday morning on a ferry.

Caribbean island hopping by boat would be the best way to see the islands. There is only one ferry that links 4 islands. 

Yes, St Lucia is linked with 3 islands: Martinique, Dominica, and Guadeloupe.

The other thing to see or do here is Pitons – the volcanic peaks south of the island. Check out the great range of Pitons hikes and day tours available.

Don’t miss our recommendations for the Top 5 Amazing Hotels in Saint Lucia . Some of these properties must be seen to be believed.

Dominica turned out to be a paradise! Its mountainous landscape offers insane views, there are waterfalls, beaches, great food and hot springs! Nicknamed “The Nature Isle”, it really lives up to its name! If you love adventure, you will love Dominica.

We hiked up to Trafalgar Falls as well as Middleham Falls. We were also set to hike up to the boiling lake, but unfortunately, due to the heavy rain, we had to change our plans.

The capital, Roseau offers markets and streets with many small eateries where you can try local cuisine and mix with locals. You’ll find many great eco-friendly places on the islands.

This is definitely the best island for independent travellers in the Eastern Caribbean with a range of great things to do .

We were warned that the beaches in Antigua (pronounced An-tee-ga ) are some of the finest. We rented a car here for a few days to see what the island offers. Our road trip started with a flat tyre within ten minutes. They say there are 365 beaches in Antigua, and we think there might be 3650 potholes on this island, too.

We stayed for a few days and enjoyed the beaches and turquoise water here.

If you’re in Antigua for just the day as part of a cruise, then this Shore Excursion to explore the whole island. The tour includes pick-up and drop-off from the port, and you’re guaranteed to be back in good time before your ship sets sail again. 

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Another flight took us to our country, number 159 St Kitts & Nevis. This dual-island nation is one of the smallest in the Caribbean, and we were almost at the end of our Eastern Caribbean island-hopping trip. This was a popular place for family vacations for North Americans and Brits.

We checked out the Atlantic and the Caribbean sides, which are only a short walk away from each other, but overall, we thought it was very quiet as it seems most people spent their day in their resorts.

Are you island-hopping the Caribbean on a cruise ship or only got the day to explore Saint Kitts? I recommend this great valued  Shore Excursion of Saint Kitts island .

The tour includes visiting famous landmarks such as Independence Square and Romney Manor, and you will have free time to swim or shop before being transferred back to the ship before departure.

The next country on our list was the Bahamas . We chose a flight that took us via the Turks and Caicos Islands. We stayed for 24 hours, and we’re so glad we stopped here. Grace Bay Beach might be up there with some of the best beaches we’ve ever seen! It was hard to leave as we love beach time!

Our flight from Providenciales (Turks & Caicos) to the Bahamas was quite a surprise. We didn’t expect to be chauffeured there in a small 16-seater ex-private jet of a retired rockstar from the 80s. Well, that’s what it felt like for us. The only thing missing was a bottle of whiskey and some canapes. It was cool.

The Bahamas is a coral-based archipelago that has over 700 islands! We stayed on the main island of Grand Bahama, although everyone will tell you that you must visit the smaller so-called family islands to see the real Bahamas.

To try and keep costs down, we stayed with a local woman in a beautiful Bahamian Airbnb house, as this country is super expensive.

The Bahamas are a popular tourist destination … here it’s all about the sun, beach, and vacation! The incredibly popular excursion to Rose Island to swim with pigs might be for you.

Due to its proximity to the USA (the island Bimini is only 50 miles from Miami), this nation caters mainly to US visitors. You can take this day trip to Bimini from Miami  or the  Bimini Express Ferry and Beach Day Pass from Miami too.

We beach-hopped, explored on foot, and explored the area in search of the 10 best foods in the Bahamas . We gave it a solid effort; the seafood, in particular is fantastic and fresh.

Jamaica was next. We hired a car and set ourselves a very busy itinerary here. We wanted to see as much as we could in the time we had. Our favourite place was Negril for the fabulous beaches, and it didn’t feel too touristy.

We spent a night at Treasure Beach, which is more aimed at independent travellers; however, Negril had a much nicer beach and vibe.

The jerk chicken and rum tasted great in Jamaica and reggae music can be heard everywhere. We swam in the Blue Hole, visited the Bob Marley museum, enjoyed cold ‘Red Stripe’ beers on white sandy beaches and met some very friendly Jamaicans.

Did you know there are  2 Jamaica languages?

This country has been on our bucket list for quite some time, so we were excited to arrive.

We booked a charming little hotel located in the historical centre in the capital city of Santo Domingo and we instantly loved the vibes here—a few reasons why we love the Dominican Republic .

It’s much more affordable than other Caribbean islands. Our hotel in Santo Domingo was $35 p/n, including breakfast, and the location was terrific! Good food and great coffee are everywhere, Uber is available, and everything feels affordable. We took buses to explore this island, different cities, beaches and areas, and we loved it!

The northern part of the Dominican Republic – Las Terrenas was our favourite. We’ll be back to eat more of the fantastic food in the Dominican Republic , too.

The Dominican Republic and Haiti share the same island – so why are they so different?

Only two more countries left to see on this leg. Next, we took a bus over the border from the Dominican Republic to enter  Haiti .

This was country number 164 and our last country in the Caribbean. We enjoyed exploring the colourful city and things to do in Cap Haitien . Our highlight was visiting the Citadelle Laferrière , what an adventure!

We really enjoyed the many flavours of Haitian cuisine, and we almost made it through these 10 best foods you should try in Haiti.  This country is fascinating, and we learned quite a few surprising things we didn’t know about Haiti .

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Tips For Travel in the Caribbean

You might also enjoy reading our post about the  11 Caribbean Islands Best Beaches to visit.

We travelled through many countries in 2019, around forty of them to be exact. We visited many Caribbean Island nations that year, and you can read our  recap of the Caribbean islands and countries visited in 2019.

Before we visited all of the island nations, we had no idea that the food would be so good! Our favourite foods in the Caribbean include these  10 popular foods in the Bahamas,  and  10 delicious dishes in Haiti that you must try!

For future travels, don’t miss our  Top 6 Travel Hacks to Save You Money  and this  Ultimate Packing List for Travellers.

And you may learn a few great tips after reading our Expert Travel Tips After 20+ Years Of Travel.

Please find our best travel tips, advice, and things we use and recommend to travel the world on our  Travel Resources Page .

Travel Planning Resources

✈️ Flights : We use Skyscanner to book cheap flights worldwide.

🏨 Accommodation :  Booking.com is our preferred platform for booking hotels and accommodation.

🏥 Travel Insurance : We recommend Heymondo ( Get 5% off Heymondo)  & SafetyWing

🚌 Transportation : Trainline is the best website to reserve trains. We use Omio to book transport worldwide. For travel in Asia, we use 12Go.  

🚘 Car Rental : We use DiscoverCars to book rental cars worldwide.

👫 Group Tours :  G Adventures OR compare multi-day tours worldwide with Tourradar .

📸 Day Tours & Trips :  GetYourGuide  & Viator are the only two platforms you need.

📚 Lonely Planet: The Best Range of Travel Guides & Ebooks , and FREE Shipping! (use code RACHELDAVEY10 for a 10% discount)

🎒 Luggage :  Osprey Farpoint 40L Backpack  or  Samsonite Luggage Range.

🛄 What to Pack:  Don’t forget your Universal charger and a good  power bank .  To help you pack the essentials, here is our ULTIMATE Packing List for all Travellers .

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20 comments . leave new.

I had no idea there was so many countries and territories in the Caribbean. Absolutely amazing facts. Always love images of Cuba with old cars. I must get there to have a look one day. Thanks for the great information. I must print it all out.

Cheers Sharon…

Thanks, Sharon. 🙂 Did you make it to the Caribbean or Cuba?

What fun to read. I am going this winter and getting ideas. I too adore Cuba though Trinidad was a bit touristy.

By the way this might interest you. http://pvewood.blogspot.com/2013/04/25-reasons-why-i-love-living-in-romania.html

Hey, I am actually going to do this starting from dom republic, I am hoping to go to Haiti after and then to Jamaica followed by Barbados and all of the island backwards. How do you recommend I should do this? I couldn’t find any flights from Haiti to Jamaica

Hi Alan, thanks for your comment. There are no direct flights between Haiti and Jamaica so you would have to either transit via Turks and Caicos or The Bahamas, but not sure if those flights connect well. Maybe you could visit the Bahamas first and then fly to Jamaica? Of course, there are usually flights via the USA (Miami often) it just means you’d have to transit there. Check out this website to find the flight connection, then you can book them online. https://www.flightconnections.com . Have fun.

Thts a fantastic idea I will go to Bahamas and then go to Jamaica after which I can do the tour as you did but backwards perfect, do you think I should be ok to cross the Dominican Republic Haiti border or I should just book the flights I am in Venezuela now and absolutely loving it

Hi Alan, we just had a friend who visited Cap-Haitien in Haiti from the Dominican Republic and had no problems. We have pretty detailed blogs on Haiti, especially on how to cross the border and what to do and eat there:

https://www.veryhungrynomads.com/border-dominican-republic-to-haiti/ https://www.veryhungrynomads.com/what-to-eat-in-haiti/ https://www.veryhungrynomads.com/things-to-do-in-haiti-cap-haitien/

Did you take flights for all of ’em? or ferries too?

We took A ferry between St Lucia and Dominica. That’s the only international ferry I believe. I have just updated the blog post with additional practical information on flights as well as on the ferry. Enjoy and happy travels.

Hi! I am also interested in traveling all the Caribbean countries. How long did it take for you to visit all of them and how many days did you need on each island?

Hi Rachel, we spent 8 weeks across these islands mentioned in the blog. On some smaller islands we spent 3-4 days, we had a week in Barbados and we spent more time in the Dominican Republic and Haiti as there was more to see. We visited Cuba a few years back, where we spent 3 weeks.

It also depends on the flight schedule as some islands are only connected with limited flights. Hope that helps.

This was so helpful!!! Can you let me know your 2 favorite islands? Because I know asking for 1 is not fair haha

Great to hear that you found the post helpful 🙂 It’s hard to choose just 2, so here are 3! We LOVE Cuba, Dominica, and Grenada.

Hi Marty, I’m planning on going and exploring the Caribbean islands in January I’m going on my own and was hoping to add Cuba, Aruba and Belize into the mix I was also considering Panama. I’m giving myself 6 months to go and see the beauties these islands have to offer. I was hoping to use ferries a lot and just book hotels before I went to each island as I don’t want to give myself any time restrictions in one place. If I like somewhere and want to spend more time there I want to be free to do so. As a solo woman is there anything you feel I should be wary of? Did you need visa to get into any of the countries? I’ve made appointments for the jabs I’ll need. I was also wondering about phone signal and internet coverage. I have to say your blog was insightful and has given me lots of ideas on what to see. And I’m sure I’ll be using it as I travel as a little guide Im hoping the locals will have lots of suggestions of things I need to see. And I get to take part in some of the festivals and carnivals. Thank you for all the advice you have given in this blog…

Hi Derri, I ma happy to hear you found the blog useful. 6 months for the Caribbean sounds awesome and yes you could probably easily add Panama as there are many flights with COPA connecting the Caribbean too. We travelled as 2 women and found the Caribbean safe, the only tip where to avoid is Santa Lucia at night at the Friday party (we didn’t go but have been warned) and if you go to Haiti read our blog on where to go and what to see. It always helps to ask a local for advice on safety.

As for hotel bookings, this is how we travelled as well: we only bought flights and hotels a few days before to allow us to go with the flow. We probably most loved (and you might like to spend some time there) Dominican Rep., Cuba, and Grenada and we really liked Dominica island as it’s very green. We spent 3 weeks in Cuba (sorry no blogs this was a few years back) and really loved it there.

You might also look into staying at Airbnb as often the host can recommend what to do and see. All the best.

Hi girls! Love your blog and your adventures! Awesome spirit! I am at 71 countries myself and shooting for 100. And a dream of mine is the southern Caribbean or Windward islands. I would love to work myself from Antigua to Trinidad (or vice versa). Your blog is super inspiring so I am really getting into planning mode here. But what I am trying to figure out and can’t really find is a realistic itinerary and reasonable logistics for someone who (unfortunately) can not be back packing for several months. I am trying to get my head around is how long travel is between the islands (unless flying) and how long to stay on each one. In your expert opinion – what is a minimum, and a realistic, time frame – if not staying one week on each island? And logistically, is there one country/island that is too complicated, and the one to cut out if necessary? Again, I am thinking Antigua/St Kitts/Dominica + Barbados/St Lucia/Grenada/St Vincent + possibly Trinidad Tobago. Would love your quick thoughts on this. Thank you so much! Daniel

Hi Daniel, you could visit those islands in a month easily. The flights are usually just over an hour but as mentioned they are not connected by ferries so flying is the best way to get around. Overall 2-3 days can be enough to get a good taste of each island… laying on the beach for a week can be done on most of them but one of the best ways is to rent a car and explore the island for a day and then spend the next day doing something unique. Maybe check the website flight connections.com to see all current flight routes and try to piece your puzzle – it’s part of the fun. Hope this helps.:)

Great blog, helped me understand better as I’m also planning to hit the 13 countries. However, I’m a digital Nomad and am depending on internet. How was the connection there? Was it easy to get sim cards with good data? Perhaps you have some info about pricing? Thanks alot

Hi Jeff, We’re glad you have found the blog to be helpful. We relied heavily on internet/Wifi in our accommodation providers during our travels in the Caribbean, as we found local SIM cards quite expensive. Suppose we had to do it all again. In that case, we’d probably buy this Airalo Regional eSIM for the Caribbean to stay connected and then perhaps source a local SIM once you arrive on an island that you’d like to stay longer on, to get access to more data.

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Are shimmering turquoise waters and white sandy beaches calling your name? When you embark on a Holland America Line cruise to the Eastern, Southern, or Western Caribbean, you’re sure to discover the enchanting beauty of the islands. From historical sites to family-friendly activities, here’s a preview of some of the things you could do as you island hop on a Caribbean cruise .

Get ready for the ultimate beach day at Half Moon Cay , our award-winning private island in the Bahamas. Though you’ll find beauty on many beaches in the Caribbean, there’s nothing like a day at Half Moon Cay. Relax to the sounds of the sea, unwind with a massage near the shore, savor Caribbean flavors, indulge in horseback riding through crystal-clear waters, or wade with stingrays as they gently swim by. Whether you’re traveling with a plus one or the whole family, here’s how to make the most of your day at Half Moon Cay .

Fun Fact: More than 700 islands make up the Bahamas, and many of them are uninhabited.

Go horseback riding through crystal-clear water at Half Moon Cay.

U.s. virgin islands: st. thomas .

You’ll be in awe of the beauty of St. Thomas in the Eastern Caribbean . Beyond the sandy beaches and crystal-clear waters, you may be intrigued by the island’s historic sites. They include Charlotte Amalie’s Fort Christian, which was built during the 17 th century, and the captivating sight of Blackbeard’s Castle.

Fun Fact: Charlotte Amalie is the largest city in the U.S. Virgin Islands, and it’s built on three volcanic spurs, known as Frenchman Hill, Berg Hill and Government Hill.

Explore beautiful beaches and historical sites at St. Thomas in the U.S. Virgin Islands.

Grand turk, turks and caicos.

Discover the charm and culture of the Turks and Caicos islands as you journey across the Caribbean. One of the sites you may want to visit is the Turks & Caicos National Museum. Housed in a historic colonial building, you’ll find artifacts from the Molasses Reef Wreck from the early 1500s, which is considered the oldest European shipwreck in the Western Hemisphere. You can also kick back and relax on a shore excursion in a Margaritaville Cabana for fun in the sun.

Fun Fact: Salt has been exported from Turks and Caicos for centuries due to accumulations of natural sea salt.

Kick back and relax as you soak up the sun at Grand Turk, Turks and Caicos.

Abc islands: aruba, bonaire, and curacao.

Prepare for paradise in the Southern Caribbean . Enjoy scuba diving in Aruba. Embark on snorkeling adventures in Bonaire at the Bonaire National Marine Park. Explore the UNESCO-listed waterfront in Curacao. Experience some of the Caribbean’s most breathtaking coral reefs, colorful street art and colonial architecture. No matter where you go, you’ll discover the wonder and beauty of the ABC Islands.

Fun Fact: The ABC Islands are just outside the hurricane belt, which means they see fewer storms than other Caribbean islands.

Immerse yourself in the beauty of the ABC Islands, including breathtaking beaches near caves in Curacao.

Considered the birthplace of reggae and home to some of the most stunning waterfalls in the Caribbean, there’s nothing quite like a cruise to Jamaica. From horseback riding and ziplining in Montego Bay to hiking the waterfalls in Ocho Rios , you’re sure to make unforgettable memories with loved ones. One of its most famous waterfalls is Dunn’s River Falls in Ocho Rios. Thousands of visitors flock to the site to explore its stair-like terrain, often with a tour guide for added safety. It’s 180 feet high and can take up to 1.5 hours to climb, but fortunately it’s surrounded by a lush green landscape, helping keep climbers cool. The falls pour out at Little Dunn’s River Beach, making it one of the few waterfalls to empty directly into the ocean.

Fun Fact: Almost half of Jamaica is 1,000 feet or more above sea level. The island is actually located at the tip of a mountain that’s mostly underwater.

Experience awe-inspiring waterfalls in Jamaica.

Calling all scuba divers, snorkelers and fun-in-the-sun seekers. Cozumel is a popular island in the Western Caribbean , attracting thrill seekers and beach goers. This cruise destination has unique attractions as well, like underwater sculpture gardens and a submarine excursion. You can also experience the world-famous ruins of the walled city of Tulum on a shore excursion.

Fun Fact: Cozumel is the largest of Mexico’s inhabited islands, covered by a tropical jungle with several archaeological sites from the Mayan period.

Snorkel above coral reefs and spot incredible sea creatures in Cozumel.

Are you ready to experience paradise in the Caribbean? Check out our YouTube video highlighting some of our 2025-2026 Caribbean cruises. Then contact one of our Personal Cruise Consultants  to begin planning your unforgettable journey.

Which Caribbean islands would you like to visit? Share in the comments below.

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Our Island Girls are fully-crewed and feature air-conditioned cabins, private bathrooms, portholes, and all modern comforts.

Your Captain sets the course. Each day is a new adventure. Free your mind from schedules, and savor each moment as the crew hoists the sails, the trade winds fill the canvas, and you set off to your next secret island destination.

There’s no rush. You’ll have plenty of time ashore to explore vibrant villages, sip rum at quirky beach bars, or laze the days away on pristine beaches.

Even the nights are magical. Shipmates gather on deck to dance, share a joke or tell tales of the day’s adventures. Lean on the rail, and steal a kiss under a canopy of stars.

Live in the now, and breathe it all in. This is island life--and you’re living it!

ALWAYS ON ISLAND TIME

2 Weeks in the Caribbean Island Hopping

DISCLAIMER: This post might have links to travel services and products that we enjoy. We might make a commission from it at no extra cost to you.

The Caribbean is a subregion of The Americas, including the Caribbean Sea and its islands. It is a large haven with over 7,000 islands, but you could visit many islands and countries through cruises and island hopping.

The West region is your best bet if you are looking for an affordable trip. It comprises Guatemala, Nicaragua, Honduras, Panama, and Colombia.

For those looking for a more lavish, high-end vacation, head to the East region, where you’ll find Turks and Caicos. British Virgin Islands, Antigua and Barbuda, Barbados, Rihanna’s birthplace, Grenada, and Aruba.

ALSO READ: 2 weeks in Costa Rica and 2 weeks in South America itineraries

BASIC TRAVEL INFORMATION FOR THE CARIBBEAN ISLAND

Planning an itinerary for 2 weeks in the Caribbean Island hopping can be a bit more complicated since transportation and visas might be challenging. Here are some tips and information to help you create your ideal travel plan.

When is the best time to travel to the Caribbean Islands

The best time to visit the Caribbean Islands is from December to April , during the dry season, when the weather is sunny and warm, making it the peak tourist season. However, December is a really high season, so the prices

The rainy season , which also coincides with the hurricane season, stretches from June to November, with September and October being the most prone to storms .

The shoulder seasons, May and November , offer a sweet spot with fewer crowds, lower prices , and relatively good weather, despite the occasional rain.

May is particularly pleasant as it’s just after the peak season and before the onset of the heavier rains, offering a balance of good weather and affordability.

Are 2 weeks enough for the Caribbean Island Hopping

Fourteen days are sufficient to explore the Caribbean Islands, offering a taste of their diverse beauty and culture. Depending on travel style and preferences, you can comfortably visit 2 to 4 islands in this timeframe.

Focusing on a specific group of islands, like the Virgin Islands, the Grenadines, or the Bahamas, allows for deeper exploration without rushing. Opting for nearby islands minimizes travel time.

Prioritise destinations with direct flights or short ferry rides to maximise your time enjoying the beaches, cuisine, and unique island cultures rather than in transit.

How to get around

The best way to get around the Caribbean Island s, especially when visiting multiple islands or countries, is through a combination of flights and ferries .

Regional airlines offer quick and efficient connections between islands, ideal for covering longer distances or when islands do not have direct ferry services.

For shorter distances or when exploring island groups like the Grenadines or the Virgin Islands, ferries provide a scenic and cost-effective option .

Chartering a private yacht or joining a cruise are luxurious alternatives that offer the freedom to explore multiple islands at a leisurely pace.

Beyond Uber, ride-sharing options in the Caribbean include local apps like BimRide in Barbados and Easy Taxi, with availability varying by island and region.

Language and currency

The main languages in the Caribbean Islands include English, Spanish, French, and Dutch, reflecting the region’s diverse colonial history.

English is widely spoken , especially in tourist areas, making it relatively easy for English-speaking tourists to get around, communicate, and access services.

In islands where English is not the primary language, such as those in the French or Spanish Caribbean , English is still commonly spoken in tourist-centric locations.

The Caribbean Islands use a variety of currencies, with the Eastern Caribbean dollar, Bahamian dollar , and the currencies of their respective colonial countries (e.g., Euro, British Pound ) being common. W hile USD is widely accepted across tourist areas , smaller establishments should carry some local currency.

Card payments are commonly accepted in hotels, restaurants, and larger shops, but cash is preferred for small purchases , local markets, and in more remote areas for convenience and ease of transactions.

The visa depends on which islands you are visiting . Most of them offer free visas to citizens with passports from Europe, North America, Latin America, Australia, New Zealand, Singapore, Japan, and South Korea.

When planning your 2 weeks in the Caribbean Island hopping, you must check each country’s visa policy to make sure you are putting together an itinerary that allows you to travel there with the passport that you hold.

Cost of 2 weeks in the Caribbean Island

Costs fluctuate significantly based on the island, season, and how far in advance you book. The peak season (December to April) sees higher prices across the board, while the off-season (May to November) offers more affordability, albeit with the risk of hurricanes.

Planning and booking ahead can secure better rates, especially for flights and accommodations. Regardless of budget, the Caribbean offers a range of options to suit different travel preferences, from serene beaches to vibrant cultural experiences.

• Affordable: Budget travellers can expect costs around $50-$100 per day, utilizing guesthouses, public transportation, and self-catering.
• Mid-Range: For those seeking comfort without extravagance, daily expenses range from $150-$300. This includes standard hotels, restaurant meals, and some activities.
• Luxury: Luxury travel starts at $300 and can go upwards of $1000 per day, featuring top-tier resorts, gourmet dining, private tours, and exclusive experiences.

Travel arrangement tips

Map of top sites and activities in the caribbean island.

Click the icon on the top right to enlarge the map. Credit: map data: Google

2 WEEKS IN THE CARIBBEAN ISLAND HOPPING ITINERARY

With the vast Caribbean, you’ll learn about different cultures, experience numerous activities, taste varied cuisines, and see diverse landscapes. You’ll get to maximize your stay here if you spend at least 2 weeks in the Caribbean Island Hopping.

With that being said, I curated different itineraries depending on your preference. If you are the type who wants slow travel or a vacation filled with jam-packed activities, or if you prefer seeing historical sites over nature and vice versa, don’t worry because I got you covered.

Itinerary #1: Barbados, Grenada, Trinidad and Tobago, and Panama

Barbados is an English-speaking country with a British vibe, so sports like cricket, polo, and horse racing are famous here. They also have high tea, so you can do so here for those who want to experience living luxuriously. It also has plantations, wildlife reserves, caves, and pristine beaches, a haven for nature lovers.

Meanwhile, there’s more to Grenada than basking in the warmth of its sun-kissed sands. It also has colourful seaside villages, rainforests, and lushly cloaked mountains. They even grow cinnamon, nutmeg, vanilla, cloves, and cocoa, which earned the country its moniker, The Spice Island.

Trinidad and Tobago is perfect for those who like dramatic topographies with unpretentious ambience, as the landscapes here are all natural. The islands are perfect for birdwatching because avian species are abundant there.

Bocas del Toro is a backpacker town with a fun atmosphere, a relaxed vibe, and an affordable cost of living. But don’t worry because you’ll always have things to try here. This will be a memorable trip from ocean-deep diving to seeing incredible wildlife.

As you might have noticed, this itinerary contains a perfect balance of expensive destinations and affordable ones. Aside from that, you’ll also get to visit 4 countries, therefore making the most of your holiday time. As there are 4 countries to see, this is a pretty busy itinerary, so planning is vital.

Barbados for 3 days

Barbados is the birthplace of rum, its caves, and beaches. It is an island country in the Caribbean region’s Lesser Antilles of the West Indies. Five places here are nominated to be considered UNESCO World Heritage sites.

Barbados is a perfect starting point as it is more developed for tourism than its nearby countries. Hence, you can buy everything you need here before starting your journey.

A must-visit locations include The Beaches of Carlisle Bay, Bridgetown Old City Center, Barbados Museum, Hunte’s Gardens, Animal Flower Cave, Barbados Wildlife Reserve, Farley Hill National Park, and more.

Grenada for 3 days

Grenada, also known as The Spice Island, is an island nation in the West Indies in the Eastern Caribbean Sea. It is famous for its harbour views, particularly St George, Grenada’s capital. Aside from that, it is also well-known for its chocolate, underwater sculptures, and historical forts.

You could do a few things here, including joining a food tour, driving around the island, taking a sunset and champagne cruise, experiencing Fish Friday, and more. Grand Anse Beach, Mt Carmel Waterfalls, and St. George City are other places to visit.

The distance from Barbados to Grenada is 171 miles, with more than two hours of travel time. You would need to fly to reach Grenada, so that is the primary mode of transport to reach your destination.

Trinidad and Tobago for 4 days

Trinidad and Tobago is the southernmost country in the Caribbean. It comprises the two largest islands, Trinidad and Tobago, and a few smaller islands. It is famous for hiking, street food, and its carnivals.

Trinidad is a busier island with impressive colonial and Renaissance-style architecture. At the same time, Tobago is a less-developed island filled with rainforests, reefs, and waterfalls and is famous for activities such as snorkelling and diving.

Top-rated tourist attractions include Port of Spain, Nylon Pool, Argyle Falls, Caroni Bird Sanctuary, Main Ridge Forest Reserve, Maracas Bay, and more. The only way to reach Trinidad and Tobago if you are coming from Grenada is by plane via Maurice Bishop International Airport to Piarco International Airport.

The travel time is more or less an hour, and tickets cost anywhere between $136 and $304, depending on the season.

Bocas del Toro, Panama for 4 days

Bocas del Toro is a province in Panama that is abundant in banana plantations and is well-known for their two national parks. Aside from that, Christopher Colombus also visited the area in 1502. It is famous for its wildlife and beaches.

Some places to visit are Starfish Beach, Red Frog Beach, Plastic Bottle Village, and Isla Zapatillas.

Like the countries listed above, the only way to reach Bocas del Toro from Trinidad and Tobago is by plane. Fortunately, there’s a direct flight from Trinidad and Tobago via Piarco International Airport to Tocumen International Airport Panama.

It’s a perfect place to end the trip because it’s more affordable, and there are many flights from Panama City to North America, Latin America, Europe, and even Asia. Check our travel itinerary for 2 weeks in Panama.

Itinerary #2: Budget-friendly (Colombia, Panama, Cuba)

The perfect 2 weeks in the Caribbean Island has to include these three countries. They offer scenic locations, balanced cost, and uniqueness.

Barranquilla has a colourful history that can be explored through its landmarks, local cuisine, and museums. Cartagena’s walled city is amazingly restored, making you feel like you’ve been transported back in time. Aside from that, it is also a well-known destination for kitesurfing.

Bocas del Toro is a perfect reprieve from the hustle and bustle of Panama City, as it is a small backpacker town. Aside from the numerous activities here, they offer many day trips to Isla Colon, Isla Carenero, Isla Bastimentos, and more.

Lastly is the city of Havana. You might’ve heard of the song Havana by Camilla Cabello. However, that’s only some of what Havana is famous for.

People also know this place for its well-preserved establishments such as Baroque buildings, museums, historic forts, public squares, and more. This second itinerary is perfect for budget travellers who want to experience historical immersion, nature trips, and adventure.

Barranquilla and Cartagena, Colombia for 5 days

The first country under this two-week Caribbean Island Hopping itinerary is Colombia. It is located mainly in South America, with insular regions in North America. It is well-known for its carnival, the Amazon rainforest, home to the world’s tallest palm trees, coffee, exotic fruits, and diverse culture.

It is the perfect starting point as it’s also close to the US and Europe, so if you want to visit these countries/continents, it would be easier. This portion of the article will focus on Barranquilla and Cartagena. Barranquilla’s charm is its colourful history and vibrant nightlife.

After all, it hosts the second-largest carnival on earth. Some places to visit here are Caribe Museum, Plaza de San Nicolas, Zoologico de Barranquilla, and more. While in Cartagena, you’ll see Old Town, Castillo San Felipe de Barajas, Getsemani, Playa el Laguito, and other beaches.

We also have an itinerary specificically for 2 weeks in Colombia .

Bocas del Toro, Panama for 5 days

Bocas del Toro is also included in this itinerary, as there are many places to visit. It is divided into two: a continental side and its archipelago in the Caribbean Sea.

Its continental side is filled with greenery and indigenous communities you can visit. At the same time, the archipelago has nine islands and thousands of islets surrounded by crystal clear waters and contains world-class surf spots.

A must-visit locations include Drago Beach, Playa Bluff, Black Rock, Isla Zapatillas, Bocas Brewery, and more. There are flights directly from Barranquilla to Panama City, with the fastest travel duration of more than an hour and the least expensive at $199.

From there, there’s a domestic flight from Panama City to Bocas del Toro with a travel time of 50 minutes and tickets starting at $70. Another option is to ride a bus followed by a water taxi.

Havana, Cuba for 4 days

Havana is the largest and the capital city of Cuba. It is also the country’s principal port and commercial centre. It is well-known for its exceptional architecture and historic centre. It is also filled with vintage cars and Volkswagens, both preserved and customized. They use these as taxis here, which is fascinating.

Some must-see attractions include Malecon, Necropolis Cristobal Colon, and Castillo de Los Tres Santos Reyes Magnos del Morro. It is the perfect place to end your trip, as there’s a direct flight from Panama City to Havana.

It’s also easy to get to Miami for those planning to extend their trip or return to North America or Europe.

Itinerary #3: Turks and Caicos, Dominican Republic, British Virgin Islands

This third itinerary I created for 14 days in the Caribbean Island Hopping is expensive but perfect for couples celebrating anniversaries, honeymooners, or a romantic trip.

Turks and Caicos comprises 40 islands where you’ll find nature trails, abundant marine life, and water sports. You’ll also get to experience lavish treatment with their luxurious resorts.

The Dominican Republic has beaches that look straight out of a movie scene, perfectly coexisting with semi-deserts. This country is the tropical escape people have been dreaming about.

The British Virgin Islands has more than 60 islands and is famous for its dive sites and natural parks, perfect for strolling with your special someone.

Turks and Caicos for 4 days

Turks and Caicos are a group of islands with eight main islands and numerous smaller islands, also called cays. It is well-known for its white sand beaches, turquoise waters, coral reefs, underground caves, and luxury resorts.

It is the perfect place to start your trip because it offers numerous watersports and relaxing places to stay, so you can both let your hair down here and unwind before starting your journey to another country.

Some must-visit tourist spots include Grace Bay Beach, Bight Reef, Chalk Sound National Park, Grand Turk Lighthouse, Mudjin Harbor, and more.

Dominican Republic for 5 days

The Dominican Republic is on the island of Hispaniola in the Greater Antilles, a part of the archipelago of the Caribbean Sea. Aside from its beaches, lush forests, and mountains, it is also well-known as a coffee, cocoa, tobacco, sugar, bananas, and mangos producer, so this is a haven for coffee and cocoa enthusiasts.

Some of the Dominican Republic’s tourist attractions are Playa Dorada, Cabarete, Las Galeras, and Samana Bay, where you can watch whales, Jarabacoa, and more.

A direct flight from Turks and Caicos via Providenciales International Airport to the Dominican Republic SDQ International Airport is the only way to reach your destination. Tickets cost between $230 and $440 with more than an hour of travel time.

British Virgin Islands for 4 days

British Virgin Islands is a British Overseas Territory in the Caribbean. It’s less popular than Jamaica, Barbados, and US Virgin Islands, but it’s definitely worth being included in your 2 weeks in the Caribbean Island hopping itinerary.

It consists of the main islands Virgin Gorda, Tortola, Anegada, and Jost Van Dyke, along with 50 smaller islands and cays. This group of islands is famous for its water sports, cruises, island hopping, and nightlife.

A must-visit locations include Fallen Jerusalem National Park, Cane Garden Bay, The Baths, Smuggler’s Cove, Brewers Bay, White Bay, and more. They offer yachting, sailing, and boat tours for those willing to splurge.

There is a direct flight from SDQ International Airport to the British Virgin Islands via Terrance B. Lettsome Airport. The travel time is more than 4 hours, and tickets cost anywhere between $55 to $410.

This is the perfect place to end your trip because you might like this place too much as it has so much to offer, and it would be easier to extend it should you wish to do so.

WHAT TO DO AND SEE IN THE CARIBBEAN ISLAND (per city)

Trinidad and tobago, turks and caicos, dominican republic, british virgin islands, local caribbean dishes and drinks to try.

Food in various Caribbean Islands is quite similar, but each has its own unique ingredients and taste. This means that if you’re visiting more than one island or country, you must try the same dishes and see which version you like best.

• Jerk Chicken (Jamaica) – Spicy, smoked chicken marinated in a mix of local spices.
• Cou-Cou and Flying Fish (Barbados) – A national dish made with cornmeal and okra, served with flying fish.
• Conch Fritters (Bahamas) – Deep-fried conch meat, seasoned and served with dipping sauces.
• Roti (Trinidad and Tobago) – A wrap filled with curried meat, vegetables, and potatoes.
• Callaloo (Various Islands) – A leafy green stew made with local greens, often cooked with coconut milk.
• Pepperpot (Guyana) – A hearty stew made with beef, pork, aubergine, and okra, spiced with cinnamon and cassareep.
• Goat Curry (Jamaica) – Slow-cooked goat meat in a rich, spicy curry sauce.
• Ropa Vieja (Cuba) – Shredded beef stewed in a tomato-based sauce, served with rice.
• Rum Cake (Various Islands) – A moist cake infused with rum, often decorated with dried fruit.
• Tres Leches Cake (Various Islands) – A sponge cake soaked in three kinds of milk, topped with whipped cream.
• Guava Duff (Bahamas) – A dessert roll filled with guava and served with a sweet, buttery sauce.
• Rum Punch (Various Islands) – A sweet cocktail made with rum, citrus juice, and grenadine.
• Pina Colada (Puerto Rico) – A tropical blend of pineapple juice, coconut cream, and rum.
• Ting with a Sting (Jamaica) – A refreshing mix of Ting (grapefruit soda) and white rum.

BEST PLACES TO STAY IN THE CARIBBEAN ISLAND HOPPING

• Affordable:

SUMMARY OF 2 WEEKS IN THE CARIBBEAN ISLAND

The Caribbean is a must-visit destination as there are activities suitable for everyone. It offers numerous activities such as diving and snorkelling for those who are adventurous and sailing and cruising for those who want a relaxing vacation instead.

Aside from various bodies of water, the countries here are also filled with forests, national parks for nature lovers, and various well-preserved archaeological sites and museums for history buffs.

Planning 2 weeks in the Caribbean Island hopping is an exciting adventure and perfect for those looking at adventure, relaxing trip, and tasty exploration.

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Ultimate Guide: Caribbean Island Hopping the Leeward Islands

Turquoise blue waters, palm fringed cabanas as you sip a coconut? Sound like a slice of heaven? During my decade plus of world travels, I’ve visited some of the world’s smallest and most remote island nations —I’ve explored more of the Pacific islands nations than most people—but there’s perhaps nowhere more fun to plan an island hopping adventure than in the Caribbean —it’s here that the island nations are close together, many are well-developed for tourism while others offer unspoiled sandy beaches and few souls in sight. 

My Caribbean island itinerary is not using a cruise ship (it’s possible!) and instead basically works south through the Lesser Antilles using a combination of short flights (often very short flights) and public ferries.

The Leeward Islands are a natural starting point and I’ll specifically share how I planned my island-hopping vacation through the Leeward Islands’ islands, before moving on to Windward Islands.

What are the Leeward Islands’ islands?

St. Thomas (USVI)

• Tortola (BVI)
• Virgin Gorda (BVI)
• St. Martin (Dutch)
• St. Martin (French)
• St. Eustatius

Each of the links above goes to a specific guide about travel on that specific island, including things to do, transportation, and more. 

Table of Contents

Transportation

Actually hopping between the islands is by far the most logistically challenging aspect of a Caribbean vacation among the Leeward Islands. Although many islands are close, the Leeward Islands are spread all over the place, meaning there is no “logical” route you can plan through the islands—this is in comparison to the fairly linear Windward Islands.

Why visit some of the smaller islands? Many of these small Caribbean islands get lumped together in people’s minds—my goal was to learn what makes each island different. In some ways they are similar (climate, geography, and history) yet in other ways they are very different (Dutch islands versus French territories versus British colonies ). Plus, the beaches, nightlife, and food is different in each place. Let’s dive into what it will take to navigate to multiple islands in Leeward Islands and Lesser Antilles.

Best Base for Island Hopping

Given the layout of the Leeward Islands’ islands, plan to base yourself in St. Martin has your hub , then you can visit about half of the key islands from there. The rest of the best spots in the Caribbean will have to be cobbled together via short flights. St. Martin works well as your base because it’s well developed and the best connected of the islands—that means you can find a gorgeous beachside place to stay, good food every night, and easy to navigate. 

If you’re starting south and island-hopping north from the Windward Islands into the Leeward Islands, or simply around that region, then St. Vincent makes a good starting point given the new Argyle International Airport, which offers great international flight connections (this could be also be a great place for island-hoppers to stop on their southerly route given the strong flight connections).

Navigating Customs on Each Island

Almost every very island you visit, unless it’s part of the same territory, requires a passport and new customs forms each time. Given how small the islands are, this bureaucracy is a huge costs the islands impose upon themselves. The region is just begging for a Caribbean Schengen-type zone, where people can travel freely between islands.

That doesn’t yet exist though, so even if you go between territories that are in theory controlled by the same country, you need a passport. Going from the Dutch side of St. Martin to either Saba or St. Eustatius requires a passport, even though they are both in theory part of the Kingdom of the Netherlands . Likewise, traveling between the French side of St. Martin and St. Bart’s similarly requires a passport check. Be prepared every time you leave your base to bring your passport, documents, and debit cards (since you’ll be changing currencies a few times as you island hop, more on that below).

Taking Ferries & Flights Between Caribbean Islands

Ferries do not run everywhere in the Caribbean islands. You can reach some groups of islands via ferry, but they will often stop at a specific island, even though another island is only a few more miles away. This means you will have to take occasional flights between islands if you want to island hop the region. The flights are very expensive considering how long they are. A 20-minute flight from Antigua to Guadeloupe cost me over $200. Approximately half the cost of any ticket in the region is taxes and fees.

So consider this: There is a ferry from the USVI to the BVI , but from the BVI to Anguilla—which is only 40 miles—you have to fly. Some of this has to do with distances, some of it has to do with the conditions of the seas between islands, and some of it has to do with economics and popularity of island-hopping routes. Some of the routes are simply plied by cruise ships and don’t receive enough independent travelers to justify ferry routes or more puddle-jumper flights.

It’s this element that makes planning a Caribbean island-hopping vacation difficult. Once you leave your base in St. Martin, you’ll need some flexibility in your timing because a one-day delay on one island will have a ripple effect through the rest of your schedule.

Island Groups Connected by Ferry:

• Puerto Rico , USVI, BVI,
• St. Martin , Anguilla , Saba , St. Bart’s ,  St. Eustatius  
• St. Kitts and Nevis
• Antigua and Barbuda , Montserrat

Additional Ferries : A ferry from Nevis to Montserrat runs two times a week, as well, so you could—in theory—travel from St. Kitts to Antigua by boat. Also, a round-trip ferry now runs two-to-three times a month from Guadeloupe to Antigua—however, the trips are only designed for people going shopping, and they don’t sell tickets if you want to go one way from Antigua to Guadeloupe.

The U.S. Dollar can be used everywhere in the region except for Guadeloupe. Technically, the Euro is in use in St. Bart’s and French St. Martin, but the proximity to the other islands means these islands commonly accept U.S. Dollars.

In theory, the Dutch territories use Antilles Guilders, but in practice, everything is in dollars. In Dutch St. Martin, items in stores were priced in both currencies, but most businesses seemed to price everything in U.S. dollars. In Saba and St. Eustatius, everything was priced in U.S. dollars.

The U.S. Dollar is pegged to the Eastern Caribbean Dollar at a ratio of 1 : 2.7, so anywhere that uses EC dollars will accept U.S. dollars. St. Kitts & Nevis and Antigua both use EC dollars in everyday usage. Anguilla uses EC dollars in theory, but everything I saw was priced in U.S. dollars.

In terms of how much it will cost to island-hop independently rather than on a cruise—this region is rather expensive.

• Gasoline prices ranged from US$6 to US$7.50 per gallon ($1.58 to $1.98/liter).
• Food prices were high, with normal meals in restaurants going for $20 on average (I never found a simple hamburger for less than US$10 at a non-fast food restaurant).
• Accommodation will add up too—there is only one youth hostel in the entire region, Butterfly Hostel in Guadeloupe, where I stayed for three nights. In the offseason, you can usually find lower end hostels for $80-$100/night, but most cost well above that figure.

Islands Culture

English is commonly spoken on all of the islands in the region except for Guadeloupe. This includes French St. Martin, St. Bart’s, and all of the Dutch islands. (More on them below).

There is certainly a common Caribbean culture seen on every island, but there are also obvious differences between each island. Many of the differences seem to be shaped by geography and colonial history. A good example is cricket, which is incredibly popular on some islands (former British colonies) and nonexistent on others.

English accents on the islands all have a similar Caribbean lilt to them, but all are slightly different. Some people have accents so thick that I had difficulties understanding them—almost as if they were a different language entirely. Many working in the tourism sector will apply a more traditional English accent when talking to tourists, and use a regional dialect when talking to friends and co-workers.

Best Caribbean Island Hopping Spots

Let’s dive into a bit about each island you’ll be visiting when you plan an island-hopping vacation of the region—this should help you decide which islands to put in your itinerary, and which are better saved for a future trip. I visited every island in both the Leeward Islands and the Windward Islands, so it’s more than possible to also hit every island—you’ll just need more time and a more meticulous plan to hop to some of the lesser-visited islands.

St. Maarten, Dutch

As with all of the Dutch islands in the Caribbean, very little seems very is Dutch about this side of the island. English is spoken as the primary language at home for locals, and you only see signage in Dutch on governmental buildings. The Dutch side of Saint Martin island is much more developed and touristy—this is where you’ll find the island’s primary international airport—Princess Juliana International Airport—and also where cruise ships dock. The Dutch side has a much more touristy feel all around than the French side.

The highlight of the Dutch side for me was the airport itself, especially the runway. The runway ends at a place called Maho Beach, where you can swim while planes fly low over your head when they land. You can also position yourself when the big jets talk off so you can be blown backward by the jet blast.

Other top things to do include water sports in Rendezvous Bay, and quick access to nearby getaways such as Little Cay or Prickly Pears Cays . You should also absolutely reserve time to explore the French side of the island.

3 Best Things to Do : 

• Small-Group Day Sail in St Maarten
• Captain Bob’s Most Popular Speed Boat, Snorkeling and Beach Tour
• Flavors of St Maarten Food Tour

Where to Stay :

• Sonesta Maho Beach Resort : This is where I stayed and it’s the closest hotel to Maho Beach. If you want to take photos or videos of the planes, this is an ideal place to stay on the Dutch side since it’s only a short walk to the runway. Just be sure to be on the beach at least 20-minutes before the scheduled arrival of a flight as most flights arrive early.
• El Zafiro Boutique Hotel : If you’re more charmed by the beach and blue waters on the Dutch side of St. Martin then this boutique hotel offers sparkling views of the Caribbean and the best spot to relax.

Other Considerations :

Take special note of using Euros on the Dutch side. While Euros are usually accepted, they’re often only accepted on par value with U.S. dollars—this is a horrible deal. Don’t use Euros on the Dutch side unless absolutely necessary.

Island Hopping To and From St. Maarten : 

If you’re making this your base (as you should) then you’ve likely arrived via an international flight, or another nearby island. From St. Maarten, ferries are generally under two hours to easily visit Anguilla , Saba , St. Bart’s , and St. Eustatius . 

Plan Your Time on St. Maarten>>

St. Martin, French

The French side of the island has a more laid back feel and it’s also the least French territory I’ve ever visited. France goes out of its way to really impose French culture on most French overseas territories . This is the only French territory I’ve visited where French wasn’t the dominant language. In smaller villages, most of the signage was in actually English. It’s only in Marigot, the capital, and other expat areas where you’ll see significant French in use.

There are a few key things to see on the French side. In addition to the capital city, Phillipsburg is the next most popular city for tourists. There is a historical fort to see, an old prison in Marigot, and an old and significant stone bridge.

• Self-Drive Boat Tour and Snorkel from Simpson Bay
• Private Sunset Cruise in St Martin
• St. Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island

Many travelers will just plan a day trip to the French side of the island—that’s likely enough unless you’re keen to really explore more deeply. 

• Villa by Hotel Les Ondines : Offers gorgeous accommodation in Marigot—it’s on the high end of the pricing spectrum.
• Sonesta Maho Beach Resort : This is where I stayed on the Dutch side and it’s a well-located base for your time on the island no matter where you want to explore.

Island Hopping To and From St. Martin : 

The two sides of the island are totally open—there are no border controls or checkpoints. That means you’ll likely arrive either by a ferry to St. Maarten or via plane. There is a small airport on the French side, but it’s only used for small planes and usually only for flights to other French islands. Most island hoppers arrive on the Dutch side and then travel to the French side of St. Martin.

Other Considerations : 

Prices are predominantly listed in Euros on the French side, although U.S. dollars are usually accepted.

The main complaint island hoppers have about St. Thomas is that is it too “developed.” Compared to other Caribbean islands, this might be true, but I still found the development level to be less than the Dutch side of St. Martin, Guadeloupe, and of course, Puerto Rico. Once you get out of the city, that feeling of over-development entirely disappears.

From Magens Bay to the Virgin Islands National Park (which takes up 60 percent of St. John island) to Blackbeard’s Castle, there are some really unique things to see when you hopping around these Caribbean islands—they are unlike others in the region! And, Trunk Bay is arguably one of the most popular beaches in the Caribbean, so you know it’s going to be a gorgeous stop on your itinerary.

3 Best Things to Do :

• Turtle Cove Snorkel and Sail Adventure at Buck Island National Wildlife Refuge
• Parasail Experience in St Thomas
• St. Thomas Mangrove Lagoon Kayak and Snorkel Tour
• Bolongo Bay Beach Resort : This is where I stayed, and while it’s not a 5-star resort, it offers solid value for a mid-level, family-owned hotel right on the beach with a great beach bar on the property. I highly recommend it. 
• The Mafolie Hotel : A good budget option that while not right on the beach, is well-priced and well-located if you are looking for a more affordable option while on St. Thomas.
• Bluebeard’s Castle Resort : Talk about rooms with views. And well priced, too!

Tortola/Virgin Gorda (BVI)

Most of the British Virgin Islands has a high end feel to it, and you’ll be hard pressed to find any area that’s truly budget or truly “undiscovered.” For perspective, Richard Branson and Larry Page have private islands nearby. That said, the level of development means it’s pretty easy to organize your island hopping around the U.S. and British Virgin Islands.

3 Best Things to Do:

You might want to plan a multi-day cruise of the islands in this group to fully explore, otherwise organize fun day trips and excursions from your base hotel. The hands-down best multi-day cruise is with G Adventures ( my favorite small-group tour company ): Sailing The British Virgin Islands – Tortola To Tortola  

• Magic Mangrove Paddle in Beef Island Lagoon
• BVI SNUBA – Go Beyond Snorkeling
• Full Day Boat Charter and Snorkel Trip

Where to Stay : 

This is not a budget area of the Leeward Islands, so you’ll likely need to splash out more cash here than you might on other islands, even for basic accommodation. I found my favorite hotel in the Caribbean here, but there appeared to be some budget options near Trellis Bay, near the airport on Tortola, if you’re on a budget (this areas also has full moon parties similar to what you might see in Thailand ).

• Bitter End Yacht Club : I stayed at this high-end resort, which caters to sailors. The Bitter End was easily my favorite hotel in the Leeward Islands. Rooms are breezy and comfortable and give a sense of privacy. I also got to go sailing on a small boat for the first time. 
• Lambert Beach Resort : One of the better budget options near the airport but still offering a gorgeous beachside resort experience.

Island Hopping To and From the BVI :

The ferry from St. Thomas to BVI is fairly easy to catch, but passport control in Road Town was far more intensive than I expected. I was told there has been drug smuggling issues on the ferry in the past, so they make you jump through more hoops on the ferry than they do if you arrive by plane. Keep that in mind when timing your day when you’re hopping between these Caribbean islands. Also note that once you arrive you can organize private transfers to get straight to your beach and resort of choice.

Plan Your Time in the British Virgin Islands>>

If you want white sand beaches, Anguilla unquestionably has the best beaches of any island I’ve visited anywhere in the world. Anguilla is the only island in the region that isn’t a volcanic island—it’s a raised coral reef. That means it’s completely made of limestone, which is the one of the key ingredients of the prettiest white sand beaches in the world.

• Prickly Pear Lobster Lunch Day Sail
• Anguilla Half-Day Sail and Snorkel Adventure to Little Bay
• Anguilla Day Trip from St Maarten: Catamaran Sail with Snorkeling at Shoal Bay

Given the super-close proximity to St. Martin, most travelers will stay there (that’s what I did) and then organize day trips to explore the best things to do in Anguilla.

• Shoal Bay Villas : An excellent option if you want to wake up to the beauty of Anguilla’s best white-sand beaches.
• The Manoah Boutique Hotel : Winning on location and the free breakfast included, this makes an excellent option at mid-range prices.

Island Hopping To and From Anguilla :

Despite having the best beaches in the Caribbean, Anguilla doesn’t see nearly as much tourism as other islands. Few large planes land in Anguilla and most visitors have to fly into St. Martin. The ferry ride from St. Marin is quick and easy—it’s a mere 15 min trip and the ferry terminal less than a 5 minute drive from the airport.

Plan Your Time in Anguilla>>

I am amazed that people are able to live on the island of Saba. Saba is one large mountain that extrudes from the sea. All of the dwellings are on top of the mountain and it seems you spend more time going up and down than you do going across the island. The island’s unique geography makes everything difficult—the airport runway is the shortest commercial runway in the world. Only small propeller planes can land, and only with specially trained pilots. There is only one road on the island (called ‘The Road’) and it wasn’t completed until the 1980’s.

Since 2010, Saba and St. Eustatius are officially part of the Netherlands . Formerly, they were part of the Netherlands Antilles, which was a constituent country of the Kingdom of the Netherlands. Despite being Dutch territory, English is the dominant language and the Saba accent is like nothing I’ve ever heard. In addition to having the smallest population of any of the Caribbean territories, it’s also the most diverse. In addition to Afro-Caribbean people, you see a higher percentage of Europeans on Saba island, as well as some Asians—many of whom attend or teach at the medical school.

Saba might be a fascinating island I’ve visited on this trip because the geography and culture of the island are so unique. It is difficult to get to, but worth the effort! Because of the topography, even though there are some great hidden beaches all over the island, hiking is one of the top activities and you can find some great routes—most hotels will offer ample advice on the best nearby trails.

What to Do : Saba Day Trip from St. Maarten —if you’re staying overnight to go hiking or experience the island culture, then it’s easy to visit on a day trip from your base in St. Maarten.

Where to Stay : Selera Dunia Boutique Hotel : Hands-down your best option on the island. It’s well priced, well located, and offers a fantastic base for exploring.

Plan Your Time in Saba>>

St. Eustatius (‘Statia’)

Like Saba, St. Eustatius (nicknamed Statia) is now officially part of the Netherlands proper. It’s unlike Saba is almost every other way.

Statia used to be the most important port in the Caribbean and was known as the Golden Rock. It changed hands 22 times in its history finally landing with the Dutch. The rich history of the island is still evident. Fort Orange is still standing and was the first place to ever acknowledge the independent United States—in November 1776 the fort fired a cannon salute to the USS Andrew Doria . You can see the stone ruins of waterfront warehouse buildings on the beach in the town of Oranjestad.

Island Hopping To and From Statia : Despite being closer to St. Kitts than any other island, the only access to Statia, by air or ferry, is via St. Martin.

Plan Your Time in St. Eustatius>>

Saint Barthélemy (St. Bart’s)

St. Bart’s is not only the most expensive island in the Caribbean, but it might be the most expensive in the world. I visited St. Bart’s on a day trip because I couldn’t justify spending over $300 per night on a hotel room (and that was during the low season!). The island was formerly a Swedish colony and was sold to France in 1878, hence the name “Gustavia” for the capitol.

Best Things to Do : 

• St Maarten Sailing and Snorkeling to St Barts
• Private St Barth Day Trip from St Maarten

The island has been thoroughly taken over by ultra-high-end boutique resorts and doesn’t really have any budget options—you’re going to have to stay in St. Maarten for budget choices. Otherwise, if you’re keen to splurge a bit your best two options include: 

• Les Ilets De La Plage : Arguably one of the most beautiful options on the island—if you’re going to splurge, go for something memorable!
• Le Barthélemy Hotel & Spa : A top-rated option in Gustavia that puts you right in the heart of all the best the island offers.

Island Hopping To and From St Bart’s :

A day trip from St. Martin is very easy to organize via ferry, with ticket prices around €80 . If you visit as a day trip, I strongly recommend not going on a Sunday—everything in Gustavia is closed save for a few cafes.

Plan Your Time in St. Bart’s>>

St. Christopher (‘St. Kitts’)

St. Kitts is the mother colony for all of the Lesser Antilles. It’s the location of both the first English and first French colony in the Caribbean.

The biggest attraction on the island is the Brimstone Hill Fortress which also happens to be the only UNESCO World Heritage Site in the Leeward Islands.

4 Things to Do : 

• Full Island Panoramic Tour of St Kitts
• ATV Tour of St Kitts
• Basseterre Food and Walking Tour
• St Kitts Deluxe Catamaran Snorkeling Tour With Lunch
• St. Kitts Marriott : I stayed here and enjoyed my time—it also has to be the largest building in the country.
• Timothy Beach Resort : This is also on Frigate Bay and may offer slightly better deals than the Marriott if you’re on a budget.

Island Hopping To and From St. Kitts:  

The island is not accessible via ferry from any other island save for nearby Nevis. If you want to visit, you will almost certainly have to fly.

Plan Your Time in St. Kitts and Nevis>>

Despite the country being called “St. Kitts and Nevis”, the country is actually a federation of the two islands and each has a very independent identity. Nevis is the much smaller of the two islands and the people seem to take a great deal of pride in being Nevisians. In 1998 Nevis had a referendum to secede from St. Kitts. The measure received 61.8% of the vote but required 2/3 to pass—they were only 197 votes away from becoming an independent country!

3 Things to Do : 

• St Kitts Shore Excursion: Nevis Beach Getaway
• Biking Round The Nevis Island
• Nevis Plantation and Beach Experience from St Kitts

Island Hopping To and From Nevis:  

I visited Nevis on a day trip from St. Kitts, which is plenty of time to see the island. Oddly enough, even though Nevis is much smaller than St. Kitts, it seems to have more high-end hotels.

There is a ferry which goes between Nevis – Montserrat – Nevis each Thursday. This is only regular means of getting to St. Kitts or Nevis by sea unless you book one of the many available day tours, that will include a chance to see top sights, snorkel, etc.

Antigua and Barbuda is an independent country, and 98% of the population lives on the island of Antigua. The geography of the island is much flatter than some other islands, which means there is more habitable land. The irregular coastline made it an important location for British harbors and today it provides many great beaches.

Because of its (relatively) larger population and geography, Antigua is a more popular tourist destination than most other islands in the Leeward Islands group, save for St. Martin.

• Southern Stingray Marine Animal Interaction and Snorkel
• Antigua Shore Excursion: Round Island Tour
• Bike, Kayak, Hike Tours Antigua
• Nicole’s Table – All about Jerk
• Antigua Yacht Club Marina Resort : This spot offers the best combination of location near the water, amenities, and a mid-range to budget price.
• Starfish Jolly Beach Resort : This all-inclusive offers a great way to relax in style and organize some of the more popular nearby snorkeling and outdoor activities.

Island Hopping To and From Antigua:  

The only ferry service to the island is to Montserrat which runs four to seven days a week, depending on the season. The airport, however, accommodates flights from all over and serves as a regional hub for Liat Airlines.

Plan Your Time in Antigua>>

Prior to the volcanic eruption of 1997, Montserrat boasted a population of approximately 12,000 people. Since the eruption—which destroyed the capital of Plymouth—two-thirds of the population has left the island, and half the landmass of the island is off limits to people.

There’s only one proper hotel on the island, which doesn’t take reservations through the major booking sites. All other accommodations are guest houses, which also have to be contacted directly.

Because of the eruptions, many of the buildings you’ll see in Montserrat are new after people rebuilt their homes and businesses on the other side of the island. The island nation is currently in the process of rebuilding a new capital in the north part of the island.

Things to Do : Full-Day Guided Tour of Montserrat

The primary attraction on the island is the volcano itself: It’s still a very active volcano, with lava having been emitted as late as May 2013. The Montserrat Volcano Observatory is open to the public, where you can learn more about the volcano and get a prime view of it. The ruins of Plymouth are off limits but can be seen either by helicopter or from boats which offer tours along the coast. 

Island Hopping To and From Montserrat:  

The airport in Montserrat is quite small and only accepts planes from nearby islands—mostly from Antigua. As mentioned above, the regular ferry service runs from Antigua, with a weekly ferry running from Nevis island.

Guadeloupe is by far the largest and most populous island in the Leeward Islands. It’s also culturally the most different, being a region of France. Guadeloupe is technically part of France in the same way that Hawaii is part of the U.S., not just a territory.

I wish I could say more about Guadeloupe, but the truth is I didn’t really go anywhere beyond my hostel. I stayed at the E Gwada hostel which, believe it or not, was the only real hostel I found in all of the Leeward Islands—that has changed (and the hostel has since closed), but hostels are few and far between when you’re island hopping the Caribbean!

Final Thoughts & Tips for Island Hopping the Caribbean

The idea of island hopping in the Caribbean is much easier in theory than in practice—the region just isn’t set up for it.

Inter-island flights are expensive. You can often fly to Miami for less than the price of a flight to an island located a mere 30 miles away. You also can’t visit every island by ferry, which adds to the expense and the hassle of getting to the islands. In many cases, you can use day tours for a moderately budget option, or private catamarans and charters if you’re keen for a direct and faster route between some of the less well-connected islands in the Leeward Islands.

In hindsight, for my own trip, it might have been smarter to attack the Caribbean in smaller units, rather than trying to do everything at once.

Nonetheless, what’s done is done. After making my way through all of the Leeward Islands, I ventured into the Windward Islands—a story for another day.

Book Your Trip

Book Your Accommodation Booking.com is hands-down the best way to book accommodation—it offers the lowest rates, and the massive community of user reviews helps you decide on the exact right place to stay, from high end hotels to budget hostels.

Find Interesting Things to Do Viator , a TripAdvisor property, offers tours all over the world. I also love GetYourGuide , a scrappy booking engine with great prices and a wide selection of tours on every corner of the earth. If you’re keen to take a multi-day tour, I’ve been on more than a dozen G Adventures tours and highly recommend the company .

Protect Yourself With Travel Insurance Travel insurance is the single best way to protect yourself and your trip from unforeseen complications, illness, theft, and more. Book travel insurance with a trusted company for your international adventure. World Nomads is the best for adventurous trips and budget travelers. International Medical Group (IMG) offers great prices for families and seniors traveling the world. The EE team has used both for more than a decade and highly recommends choosing the one that best fits your next trip.

Pack the Necessities I carry a lot of travel gear , but I never leave without my travel adapters. This Glamfield one is my favorite: It features three USB chargers, USB-C, and adapts to most plugs anywhere in the world! If you’re looking for a lower profile adapter, however, you can’t go wrong with this one (I carry both!).

31 thoughts on “Ultimate Guide: Caribbean Island Hopping the Leeward Islands”

Did you finish your Windward island hopping trip? I was trying to find it on your website, but was unable… My friends and me are off to Caribbean next weekend for 2.5 weeks, flying to Martinique, and planning to do some trek in Dominica and Guadalupe and probably St. Lucia, but don’t know if it’s worth it. What was your experience of these islands? Thanks, Alex

Will be there in 30 days, your post give me great Ideas. Thanks

Wow! After reading this post my next destination is Caribbean region for sure! Thank you for it!

Island hopping in the caribbean really isn’t easy for my part I decided to do it like the “old” folks ;-) on a cruise ship. This gives you a good overview of the different islands in a short amount of time and without spending to much money. So you can then decide later on which island you really want to spent some time on. Personally, I really liked Barbados.

Ohhh!!! When I see this photos I want to be in these places!!! :)

Love how you spent the time to write such a detailed and comprehensive post. I hope your readers take everything in instead of skim reading! Monsterrat sounds amazing, I would love to go see the volcano.

That is kind of disappointing. Like you said, it looks perfect for a Eurozone type grouping. Given how many tourists come, I am surprised the ferry system doesnt go everywhere. BTW do you ever post the logistics of your expenses? Not that I am nosy, but I wanna think about what I am looking at if I plan a trip there.

The great detailed post

Such a detailed post.

Enjoying traveling vicariously with you through the Caribbean! St John is one of my favorite islands!

I’m really enjoying following along, can’t wait to read more. The Caribbean is one our favorite travel destinations so you have our attention for sure! Happy Travels!

This is a great overview. I’d love to island hop sometime. So far I have only visited Grenada and it definitely whetted my appetite.

Your Carribean island hopping adventure is so awesome! I have experienced island hopping but not cool as yours. We only visited I think 3 small islands and it’s only 15 minutes away from each other. I agree with you that island hopping in the Caribbean is much easier in theory than in practice. It’s not like the movie Pirates of the Caribbean that uses the Black Pearl to sail the different islands for free. ha ha ha..

I salute you on this experience, Gary.

Thanks for the great detailed post! Ive been wanting to do this before we left for Costa Rica last year! …still in Costa Rica lol haha but this is definitely something we will do… thanks a bunch for the great post!

Thanks for such a detailed post. I’d heard it is difficult and expensive getting to a few islands. Seems like transport could use a bit of an upgrade.

You know that “most interesting man in the world” guy? He’s got nothing on you. Wow!

Looks like great fun on the beach. Nice to know that US currency is acceptable on some of the islands.

Guess the best way to visit the whole Caribbean would be on a sailing boat.

Awesome, would love to go island hopping one day!

Glad to see I can use the USD when/if we ever make it to the Caribbean Islands. Thanks for the very useful information but I dont know when I would have a chance to ever island hop. Maybe just one hop every now and then. They are expensive thats a lot of money for gas.

What an amazing trip! Seems rather expensive, however, going from island to island.

Wow, I’ve been to a few Caribbean islands in short bursts but I think the way you’re doing it is great. Even if it is a bit more challenging. I think I’d be pretending I was a pirate, island hopping! Love that the islands you’re going to are a bit out of the ordinary too!

This is very neat what you are doing! I’d like to island hop the in the Caribbean one day! I look forward to your future posts about your experiences there! Are you considering Curacao? I really enjoyed that island!

I am so jealous. I would change cloudy London for (even rainy) Caribbean right now.

Amazing! I wanna go there right now!

Nice post with complete information . Like the way you categorize post Transport , culture , money …Really looking forward for your other blog post .

Just read your post on Antigua, here is what you need before you visit Barbuda!

This is all great information! Very informative. I feel like I learned something new. :)

Amazing! I understand the struggle and annoyance trying to get from island to island but what an incredible experience. I’m very jealous

Hey Gary: How about that take-off and landing on Saba, think it’s the shortest runway in the world, requires a STOL aircraft and a shot of Jack Daniels. Stay well my friend, JSC

Comments are closed.

Reader's Digest

The Best Caribbean Cruise for Every Type of Vacationer

Posted: July 29, 2023 | Last updated: July 29, 2023

Get ready to set sail in the Caribbean

It's no wonder cruising in and around the Caribbean is so popular. But with so many ships—50,000 yearly—offering up exciting itineraries from a variety of departure ports, not to mention the number of islands the ships call on, finding the best Caribbean cruise can seem downright overwhelming! We're here to help by breaking down the options with all the best Caribbean cruises. Whether you want an affordable warm-weather family cruise, a luxury couples getaway or a solo cruise to meet new people, we've got the scoop.

If you're in the market for the best deal on a Caribbean cruise, there are two seasons to be aware of. Between January and March is what's known as "wave season." This is when the cruise lines promote deeply discounted fares for the best Caribbean cruises. Or you can choose to shop around for sailings during the fall, when prices tend to be low because of hurricane season. Don't worry, though—the captains of the ships are well-versed in avoiding stormy weather.

How we chose the best Caribbean cruises

Not only did I rely on my own personal experiences at sea (I've taken eight cruises in the past year alone, and I've been cruising for about a decade), but I also scoured websites to find the  best cruise lines based on the many different types of travelers, from those who want to snorkel every day to cruisers who want nothing more than a sunny deck chair by the pool. Now, all you need to do is brush up on all the things you can't do on cruises , discover the many hidden cruise features , decide if you want to add on a stay at one of the most glamorous all-inclusive Caribbean resorts before or after your cruise , and then book your vacation!

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Best overall

Celebrity cruises.

With a breathtaking mix of elegant ship design, gorgeous cabins, delicious restaurants and luxurious outdoor spaces—including a rooftop garden, martini-glass hot tubs seemingly floating in mid-air, the adults-only Solarium and the thrilling Magic Carpet lounge jutting out over the water on the Edge-class ships (Beyond, Edge, Apex and the forthcoming Ascent)— Celebrity is our choice for the overall best Caribbean cruise. Plus, the Edge-class ships feature a unique main dining room concept that not only soars above other cruise lines' complimentary dining options but also the majority of the fee-based specialty restaurants that I've dined at. Each of the four main dining destinations has stunning, regional-specific design elements, shared and individualized menus and top-notch service.

Additionally, the Celebrity spa and its thermal suite are the best at sea for affordable luxury and ultimate relaxation while island-hopping. If you're looking for the best cruises for couples in the Caribbean, it's hard to beat the affordable elegance and sheer class of these ships.

• 11-day southern Caribbean itineraries with a port of call in Cartegena, Colombia
• Three top-notch complimentary main dining rooms
• Eden, the live entertainment venue that's home to more than 5,000 live plants
• The spa's SEA Thermal Suite is the apex of relaxation
• Lack of outdoor activities like waterslides and rides for families
• The theatrical stage shows sometimes disappoint

Best budget

Carnival cruises.

For decades, Carnival "fun ships" have been the premier choice for cruisers looking for ways to travel on a budget . Carnival is still competitively priced, still hosts hairy-chest contests and a St. Jude charity dance party, and still ranks as one of the best Caribbean cruises you can book for less. Better yet, the newest ships in the fleet have added a touch of class thanks to the Brass Magnolia, a cool, new jazz club. Overall, we love the fact that you can have a ton of fun on board Carnival cruise ships in the Caribbean, not just in the most exciting ports, like Nassau in the Bahamas, Ocho Rios in Jamaica, and Cozumel, Mexico. On the ships, you'll find colorful water parks with twisty waterslides, the Bolt roller coaster and the Red Frog brew pub. While the ideal time of year to cruise the Caribbean is usually from January to April during the Caribbean's dry season, Carnival makes visiting the islands fun any time of year.

• Affordable prices starting at under $500 per person for a week in the Caribbean
• Guy's Burger Joint and Smokehouse offer some of the best free food at sea
• Superb live music and theatrical entertainment
• Exciting kids camp partnership with the Kennedy Space Center on Carnival Celebration
• Low prices make Carnival one of the best cruise lines for kids as well, which means couples and seniors may find these ships too loud and busy

Best for kids

Disney cruises.

The best cruises for kids and families will naturally be focused on the joys of childhood and the unique needs of children from start to finish. That's definitely true on Disney cruises , which pay as much attention to the bright and fun design of the staterooms as they do to the interactive restaurants, bars and lounge experiences that call on Marvel,  Star Wars and Disney's famous animated characters. (These are all exclusively on Disney Wish.) In my experience, the kids clubs—with Marvel superhero school, Jedi training camp and never-ending arts and crafts—are where Disney truly excels. In fact, your elementary-school-aged kids may never want to leave!

Another high point are the Broadway-caliber shows, including Aladdin , Frozen and The Little Mermaid . So put on your mouse ears or grab your lightsaber, check out these  Disney cruise tips , and book a magical Caribbean cruise with Disney.

• Character meet-and-greets and multiple interactive dining experiences
• Themed sailings for Marvel, Pixar and Star Wars fans
• First-run Disney films premiering in the onboard movie theaters (think: the live-action Little Mermaid )
• Access to Castaway Cay, a private Caribbean island
• Cost-prohibitive for many families

Best for luxury lovers

Scenic cruises.

The world's first discovery yacht, the Scenic Eclipse , which spends part of the year exploring the Arctic and Antarctica, is now bringing guests to some of the most exotic small ports of the Caribbean. Scenic is one of the best Caribbean cruises for the traveler who wants to experience remote escapes for a more culturally authentic vacation in well-traveled waters. You will visit ports such as Darby Island, Egg Island and Long Island in the Bahamas, Puerto Rico's Isla de Culebra, Grenadine's Mayreau and Colombia's Isla de Providencia, as well as have the opportunity to make a full Panama Canal voyage.

And the joy of cruising the Caribbean on this luxury small ship isn't limited to the destinations—you'll enjoy extraordinary onboard experiences too. Let's start with the fact that there are private butlers for each cabin and suite, and just 228 guest maximum on any given sailing, with almost a 1:1 crew-to-guest ratio. You'll also find 10 dining options, premium beverages and all airport transfers and gratuities included in the price. Plus, once-in-a-lifetime immersive excursions and enrichment experiences, like floating through mangroves and small caves in glass-bottom kayaks, are all complimentary. With everything covered and handled on a Scenic Caribbean cruise, the only thing you'll need to worry about is figuring out what to pack .

• Private butlers and a nearly 1:1 guest-to-crew ratio
• Remote ports of call accessible only on a small ship
• Truly all-inclusive , with even excursions included in the price
• Lack of diverse activities and entertainment on board

Best for LGBTQIA+ travelers

Virgin voyages.

Virgin took to the Caribbean Sea a few years ago with the aim of disrupting the cruise industry. Its cruises feature cabins that convert to social spaces thanks to beds that become seating areas, and swing hammock chairs on private balconies, and nearly everything is rolled into the main price—including restaurants, Wi-Fi, group exercise classes and gratuities. In short, Virgin comes the closest to offering affordable all-inclusive cruises . With no kids under 18 allowed onboard, the upstart cruise line was and still is a breath of fresh air for cruisers looking for adults-only cruises .

The most exciting thing about Virgin Voyages, however, just may be the "come as you are" vibe on their cruise ships. Crew members are allowed to show off their tattoos and piercings, and the ships have unisex bathrooms, sexy shows, raucous parties and a genuinely welcoming atmosphere for LGBTQIA+ cruisers, making them feel safe and seen in the sunshine of the Caribbean.

• A "come as you are" vibe
• Sexy, adult-oriented entertainment, dances and parties
• Private Bahamian beach experiences and parties that go late into the night
• All food, many beverages, Wi-Fi and gratuities included in the cost
• Vegan dining at Razzle Dazzle
• Families, even those with worldly teens, aren't able to cruise on Virgin Voyages

Best for Texans

Norwegian cruise line.

The brand-new Norwegian Prima is an amazing Caribbean cruise for families—both because of its features and its accessibility to different parts of the country. Those family-friendly features include go-kart tracks spanning multiple decks, virtual reality games, an escape room, thrilling dry and wet slides hanging off the edge of the ship, and a neon sports area featuring mini golf, dart rooms, pickleball courts and so much more. And thanks to departures from both Galveston, Texas, and New York City, the Caribbean has never been more accessible to so much of the country. From Texas's south coast, Prima easily reaches southern Caribbean ports like Roatán and Belize, while travelers departing from New York can cruise all the way down to St. Kitts, the Dominican Republic and the British Virgin Islands, with a stop in Bermuda on the way back, without having to get on a plane first. Whether your family is in the Midwest or the Northeast, Norwegian puts the Caribbean right at your doorstep.

• Departs from Galveston, Texas, and New York City
• Access to a private Caribbean island for exclusive beach time
• A go-kart track spanning three whole decks, and a massive virtual reality gaming room
• Studio staterooms for solo travelers
• Go-kart drivers must be under a set weight, which means some family members may not be able to drive

Best for action lovers

Royal caribbean oasis class cruises.

Like a thriving city at sea, Royal Caribbean's Oasis Class ships offer up more fun, entertainment and activities than most people can even see and do during a typical weeklong cruise! It is nearly impossible to be bored on an Oasis-class ship. That's why these vessels are the best Caribbean cruises for anyone who wants to try new things like ziplining or simulated surfing, feel nostalgic riding a carousel on a boardwalk, or see Broadway-caliber theatrical shows inside and out.

While they are some of the biggest cruise ships at sea, these vessels were cleverly designed to make it not feel like you are surrounded by upwards of 6,000 other passengers. There's so much to see and do on Royal Caribbean in the Caribbean, you may not even have time to ponder those strange white balls on cruise ships , but if for some reason you do get bored, know that you've got Perfect Day at Coco Cay to visit. This is arguably the best private island in the Caribbean, and you can spend a day here ziplining, riding in a hot-air balloon, chilling out by one of many pools or playing in an incredible waterpark that features North America's tallest waterslide.

• Multipurpose deck that serves up ice skating and ice shows, then transforms into a laser-tag arena
• The tree-lined Central Park neighborhood in the center of the ship is literally a breath of fresh air at sea
• Interior rooms have balconies and views of "Central Park"
• Every itinerary includes a trip to Perfect Day at Coco Cay, a private island paradise
• Oasis-class ships may feel too big for some cruisers

Best for cultural explorers

Windstar cruises.

Thanks to departures from Caribbean ports like San Juan, Puerto Rico , and Bridgetown, Barbados, Windstar allows you to spend less time in transit and more quality time in places like St. Barts, Montserrat, St. Maarten, Barbados and the British Virgin Islands. Not only are these budget-friendly luxury smaller ships fabulous, but the excursions also offer the opportunity for you to make deep dives into the history and traditions of some of the most culturally rich islands in the Caribbean. You'll meet locals who will invite you into their homes, teach you to cook with their herbs and spices, and provide you with experiences that showcase why travel is so important in the first place.

There are itineraries covering two distinct sides of the Caribbean: Eastern and Western. The Eastern side is where you'll find more cultural and historical ports of call, with some great shopping too. The Western side is better known for water sports and fun in the sun on white-sand beaches.

• Intimate excursions that explore the culture and traditions of each island
• Option for a 35-day grand Caribbean adventure
• Windstar's Signature Beach Party on a secluded beach with a buffet lunch and free water sports
• Onboard poolside barbecues
• Not a robust selection of onboard activities or entertainment

Best for seniors

Princess cruises.

If you're of a certain vintage that fondly recalls the TV show  The Love Boat , then Princess Cruises is the best Caribbean cruise for you! It was a Princess ship featured in that classic show, and they still call it The Love Boat, so nostalgic seniors will think that Princess Cruise Line ships are the bee's knees! But Princess is one of the best Caribbean cruise options because the ships have a retro elegance about them, an old-fashioned level of class with shiny brass decorative elements, elaborate chandeliers, familiar tasty food, upscale wine tastings, cultural enrichment programs, Deal or No Deal games on the main stage, Broadway-style entertainment, and The Love Boat Piazza Party on one of your formal nights.

Additionally, seniors will enjoy knowing that on every Princess ship cruising the Caribbean, there are many ADA cabins with full wheelchair-turning space, roll-in showers with grab bars and a fold-down bench seat, as well as closets and desks that are both cleverly designed and highly accessible. Princess Cruises also offers one of the best Alaska cruise itineraries.

• Numerous ADA-accessible staterooms across all cabin types (from suites to interior rooms)
• Old-school elegance
• May feel too old-timey for some travelers

Best for sailors

Star clippers.

These classic clipper ships have sails that aren't just for show—they are actually powered by the wind whenever possible! When it's time to sail away to a new island, the ceremonious hoisting of the sails, which is accompanied by the epic strains of "Conquest of Paradise" from the movie 1492,  is a truly breathtaking sight to behold. And here's an interesting fact : Star Clippers holds the Guinness World Record as the world's largest full-rigged sailing ship. The five-masted vessel is a beauty and a throwback to another era of seafaring. While the big ships may have ziplines and ice-skating rinks, on a Star Clippers cruise you can lounge in a net suspended high above the sea and kayak or stand-up paddleboard off the marina platform at the rear of the ship.

• A working sailing ship that transports you to another era
• Sailings start and end in the Caribbean
• Access to small islands like St. Lucia and Martinique and Virgin Gorda
• "Treasure Island" itinerary visits a host of small, intriguing Caribbean islands that you won't get to experience on the bigger cruise ships
• Pirates don't mind the rough seas on a sailboat, but you might on a Star Clippers cruise
• Pirates also don't need a lot of entertainment options on board, so don't expect Broadway productions on these ships

Best for LEGO fans

Msc cruises.

While we love the F1 simulators and the full-size bowling alley on MSC cruises , spending a week at sea on this Caribbean cruise is really all about LEGO for us. MSC and the LEGO Group have an exclusive entertainment partnership that gives kids the chance to play and build with LEGO bricks in colorful areas of the ship designed just for them in the Mini and Juniors clubs. But the LEGO (and Duplo) fun isn't confined to the kids clubs. Once during every Caribbean cruise, there's an entire day dedicated to LEGO activities for kids of all ages to enjoy, LEGO diplomas to earn, and parades to watch.

But, of course, it's not really  all about LEGO. For environmentalists and cruisers looking for a relaxing private island escape with miles of white-sand beaches with chairs, umbrellas and cabanas calling your name, MSC's Ocean Cay MSC Marine Reserve is a sheer delight. It's a biodiverse and sustainable environment with coral reefs being relocated and saved, and you get to explore it on your trip.

• LEGO fun for kids, with loads of play areas and activities
• MSC Meraviglia departs for the Caribbean from Brooklyn, New York
• Late-night and overnight stays on MSC's exclusive private island in the Bahamas, Ocean Cay MSC Marine Reserve
• Not as many onboard activities for families as the other big cruise ships

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I went on 2 of Royal Caribbean's largest and newest cruise ships. I enjoyed them, but they're not for everyone.

• I've sailed on Royal Caribbean's largest cruise ships , Wonder of the Seas and Icon of the Seas.
• Both megaships are jam-packed with people, amenities, and dining options.
• But if you want a quiet cruise to unique destinations, they might not be for you.

Before booking a vacation at sea, travelers should always research the best cruise line and ship for their needs.

If you're looking for a cheap and fast trip, try Margaritaville at Sea . Craving something more upscale? Consider Oceania Cruises.

But if you're looking for high-end sailing to unique destinations, I'd suggest avoiding Royal Caribbean's megaships .

Royal Caribbean has become synonymous with giant, family-friendly cruise ships

By 2028, Royal Caribbean wants one-third of its fleet to be megaships.

The latest addition, the 1,196-foot-long and 248,663-gross-ton Icon of the Seas, entered service in January, unseating Wonder of the Seas as the world's largest cruise liner.

Together, the two vessels can fit over 19,000 people — about 4,500 crew and 14,500 guests. Each ship has eight neighborhoods and there are 29 bars and 48 eateries between them.

I've attended complimentary sailings on both Wonder and Icon, the longest of which was three nights on the latter. From their colorful pool decks to the inescapable crowds, as a solo-adult traveler, I was equal parts entertained, overwhelmed, and overstimulated.

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But admittedly, I had fun. I do love a good waterslide; Wonder has three of them and Icon has six.

If you want to go on a cruise with your children — and if they, like me, love activities like rock climbing and mini golf — Royal Caribbean's megaships could be your best option.

Wonder and Icon are jam-packed with activity spaces like ice-skating rinks and ziplines.

But don't expect a peaceful retreat. The rowdy, bar-hopping adults and screaming children at the water playground aren't conducive to a relaxing vacation.

Megavessels might not be for you if you want a quiet cruise

If you want a relaxing vacation — maybe one that doesn't involve crowds of children — you shouldn't stay on either Royal Caribbean yacht.

There are many ways to have a luxury vacation on Icon of the Seas . But unless you want to pay for upcharged amenities at every turn, you'd be better off spending more upfront to reserve a premium cruise line — especially if you're interested in cruising for the destinations, not the ships.

After all, like most of Royal Caribbean's largest vessels, Icon and Wonder exclusively sail in the Caribbean.

Some destinations, such as French Polynesia, have set restrictions on which cruises can travel there amid concerns about pollution and overcrowding.

If stopping at these ports — or, really, anywhere outside the Caribbean — is at the top of your vacation wish list, you'll have to travel on a smaller Royal Caribbean ship or go with a different cruise line like Oceania , Silversea, and Regent Seven Seas.

You might not get a waterpark, but you'll get a quieter vacation to locations no megaship will likely be allowed to visit.

Watch: Inside the world's biggest cruise ship that just set sail

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