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 travellers looking to mix things up and broaden their experiences can find an array of exciting possibilities when planning a multi-island trip.

“he real trick is knowing which islands have manageable connections.  A lot of Caribbean islands can be easily clustered together based on proximity, but also on national affiliation.


There is new air service from Nevis to St. Thomas.
Credit: 2023 Nevis Tourism Authority

Indeed, picking destinations that complement one another is important when it comes to planning a multi-destination getaway. Some travellers 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. 

I recommend 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 nine seat King Air B200 and is part of the hotel’s VIP Transfer add-on package. 


Bequia Beach Hotel offers its own flight service.
Credit: 2023 Bequia Beach Hotel

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, five square-mile island. *subject to change.

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 travellers 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. 

Canadian travellers need a passport valid six months after their trip return.

I’m ready to work with you to create a unique travel experience based on your travel destination, style, and interests. Please touch base so I may answer any questions you have and provide you with expert travel advice.

Disclaimer: Current travel rules and restrictions can change without notice. The decision to travel is ultimately your responsibility. Contact your consulate and/or local authorities to confirm your nationality’s entry and/or any changes to travel requirements before travelling.