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Island Hopping The Caribbean—How To + Itinerary Ideas

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.

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.

Public Ferries

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.

Riding a boat to Anguilla
Ferries are an affordable option for Caribbean island hopping.

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!

Cruise Ships

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.

Charter or Rent a Private Yacht or Boat

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.

Flights

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.

Plane flying over palm trees Caribbean island hopping
Flying between islands can be quick but not always convenient

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.

Nassau

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.

Lighthouse in Nassau Bahamas Caribbean island hopping
Nassau Harbour Lighthouse

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.

Aerial view of lagoons on Long Island, Bahamas, Caribbean island hopping
The Bahamas is home to amazing blue lagoons.

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.

Harbour Island

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.

Pink Sand Beach on Harbour Island Bahamas Caribbean island hopping
Soft pink sand awaits you on Harbour Island.

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.

Eleuthera

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 Island Bahamas Caribbean island hopping
Two oceans collide at the Bight of Eleuthera.

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.

Exuma

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.

St. Martin/Saint Maarten

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.

Great Salt Pond St Maarten Caribbean island hopping
Philipsburg, on the Dutch side of the island.

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.

St. Barts

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.

Beach at St Barths Caribbean island hopping
Get ready to spend some cash on St Barths.

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

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.

La Datcha Beach Guadeloupe Caribbean island hopping
La Datcha Beach in Guadeloupe

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.

Turtle on dive wreck Caribbean island hopping
Don’t forget to pack your GoPro.

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.

And even further:

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

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

St. Lucia

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.

Adventure

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.

Woman at Sulphur Springs mud baths things to do in St Lucia
Why not add a mud bath to your Caribbean island hopping adventure?

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

Stairs to lookout at Pigeon Island National Park things to do in St Lucia
See the coast of St. Lucia from Pigeon Island National Park.

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.

Food at Jambe de Boi restaurant best beaches in St. Lucia
Local Caribbean food at Jambe de Bois, St. Lucia

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

Beaches

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.

Soufriere Beach things to do in St Lucia
Views of the Pitons from Soufriere Beach

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!

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.

The Baths on Virgin Gorda Caribbean island hopping
The Baths on Virgin Gorda

The British Virgin Islands

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.

Tortola British Virgin Islands Caribbean island hopping
Make Tortola one of your Caribbean island-hopping stops.

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.

Antigua and Barbuda

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.

Antigua Shirley heights
Shirley Heights in Antigua

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

The U.S. Virgin Islands

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.

Cable car over St Thomas Caribbean island hopping
Cable cars over St Thomas

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

Caribbean Island-Hopping Travel Guide #4: Turks and Caicos

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.

Turks and Caicos Islands Caribbean island hopping
The blue waters around Turks and Caicos Islands

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.

Adventure

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 jetski out to an old shipwreck, kayak through stunning cays around Providenciales, or explore caves in Middle Caicos.

Jet ski at La Famille Shipwreck things to do in Turks and Caicos
La Famille shipwreck on Turks and 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.

Kiteboarding on Long Beach things to do in Turks and Caicos
Kiteboarding off Long Bay Beach

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.

Food and Culture

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.

Selection of food and drink things to do in Turks and Caicos
Fresh cooked seafood on Turks and Caicos

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.

Beaches

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.

Swimming at Grace Bay Beach best beaches in Turks and Caicos
Don’t miss Grace Bay Beach when island hopping in the Caribbean.

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 for the Adventurous

Caribbean Island-Hopping Travel Guide #5: Montego Bay, Jamaica

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

Adventure

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.

Montego Bay Jamaica Caribbean island hopping
Picturesque Montego Bay

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.

Food and Culture

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.

Cooking street food on the beach Caribbean island hopping
Jamaica has great restaurants, but don’t skip the street food!

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.

Beaches

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.

Beach at Montego Bay Jamaica Caribbean island hopping
Caribbean island hopping is all about beaches.

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.

Check Your Visas

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.

Boat at Half Moon Cay Bahamas Caribbean island hopping
Check the visa before you get on a boat

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.

When to Go Island Hopping in The Caribbean

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.

Pack Light

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.

Woman with drybag Caribbean island hopping
Pack light for your Caribbean island hopping trip

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!)

Set Up a Base

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.

Don’t Rush

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!

Beach bungalows in Eleuthera Caribbean island hopping
Make sure your Caribbean island-hopping adventure includes time for chilling.

Compare Quotes

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.

Safety First

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.

Plane over Philipsburg St Maarten Caribbean island hopping
Smaller planes make for easy trips between islands.

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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