The Ultimate Guide to Caribbean Island Hopping

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

A view of Cane Garden Bay on Tortola in 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.

St. Lucia

The World Heritage Petit Piton framed by beautiful infinity-pool. View from the famous resort Jade Mountain.

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?

About The Author
Jim is the founder of He loves the Caribbean and wants to share it with everyone he can. He has been traveling in the Caribbean since he was just 18 months old and has seen most of its beautiful beaches and turquoise waters.

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