The Ultimate Guide to Caribbean Island-Hopping

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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, 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 Viceroy 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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