How to Plan a Seamless Caribbean Island-Hopping Vacation

There are more than 7,000 islands in the Caribbean — so why limit a vacation to just one?

Each destination in the Caribbean has its own unique charm, of course, and there are many reasons to stay put on just one island. But travelers looking to mix things up and broaden their experiences can find an array of exciting possibilities when planning a multi-island trip.

“The real trick is knowing which islands have manageable connections,” said Lee Friedman, founder of Washington, D.C.-based Mango Tree Travel, an affiliate of Jetset World Travel and a Virtuoso member. “A lot of Caribbean islands can be easily clustered together based on proximity, but also on national affiliation.” 

Indeed, picking destinations that complement one another is important when it comes to planning a multi-destination getaway. Some travelers may want to contrast a larger island with a smaller one, or a Dutch-speaking island with an English one, for example. Some might prefer a laid-back ferry ride to travel between islands, while others might prefer the convenience of a plane or private charter. 

And connectivity is improving in some parts of the Caribbean, making it easier to combine certain destinations. Earlier this year, InterCaribbean Airways launched new nonstop flights linking St. Kitts and Barbados and also upgraded its flights between Grenada and Barbados from Embraer 120 to larger ATR-42 aircraft. 

Even some hoteliers are helping vacationers realize their island-hopping dreams. Sandals, for one, offers a Honeymoon Hop program for couples that includes custom-designed itineraries with flights between islands such as Antigua, Grenada and Barbados, with romantic activities and accommodations at Sandals properties at each stop. 

Friedman recommends several Caribbean island combinations, including the ABC islands (Aruba, Bonaire and Curacao); the many islands of the Bahamas; and St. Lucia, Martinique, Guadeloupe and Dominica, all of which are connected by ferry service L’Express des Iles. 

Here are some other possibilities for combining multiple destinations in one Caribbean vacation. 

Anguilla and St. Martin 

Belmond is among the hoteliers making it easier to create multi-stop vacations. Guests staying at its Cap Juluca property in Anguilla and La Samanna hotel in St. Martin can make use of the brand’s semi-private 25-minute boat transfer service. Also worth noting in Anguilla: This year, a new, 18,336-square-foot ferry terminal debuted at the port of Blowing Point, complete with a VIP reception area and six immigration stations. 

Barbados, St. Lucia and the Grenadines

In the Grenadines, Bequia Beach Hotel offers its own flight service, Bequia Air, which links the island with Barbados and St. Lucia. The service is operated with a 9-seat King Air B200 and is part of the hotel’s VIP Transfer add-on package. 

St. Maarten and Saba

St. Maarten-based Winair recently increased its daily service to the Dutch Caribbean island of Saba, and also launched a new daytrip fare of $140 roundtrip for vacationers hankering to spend just a few hours on the picturesque, 5-square-mile island. 

U.S. Virgin Islands and Various Destinations 

The U.S. Virgin Islands, which itself is made up of three large islands and many smaller ones, is also well-positioned for Caribbean exploration. In February, Cape Air launched new nonstop service from St. Thomas to Nevis, whisking travelers to the nearby island in just over an hour. Those looking to explore the British Virgin Islands, meanwhile, can hop aboard a scheduled, 50-minute ferry service operated by Road Town Fast Ferry from Charlotte Amalie, St. Thomas, to Road Town, Tortola. 

It's even possible to island hop without a passport. U.S. citizens and permanent residents can travel with nothing more than a driver’s license between the U.S. Virgin Islands and Puerto Rico. Cape Air links St. Thomas and St. Croix with multiple Puerto Rican destinations, including San Juan, Vieques, Mayaguez and Culebra.