When people find out that I'm one of the main Caribbean editors here at Fodor's, the one thing almost everyone wants to know is which island in the Caribbean is the "best." It's one of the most common question posted in our Caribbean user forums. The truth is there is no "best." Each Caribbean island is unique, and everything depends on what you're looking for.
If you know yourself and know what you want, you can come pretty close to perfection in the Caribbean. But that's often easier said that done. To help you jump-start your winter or spring vacation planning, here are some suggestions for all kinds of travelers. See which of these major interests best describes you; perhaps these questions will help you narrow down your choices.
I love beautiful beaches
Well, who doesn't want a beautiful beach on a tropical vacation? You'll find at least one beautiful beach on almost every Caribbean destination you can imagine. I'd ask you to dig a little deeper to find something else that will help make your choice a bit clearer. If you aren't interested in digging deeper, then take a look at Anguilla, the Turks & Caicos, Aruba, Grenada, the U.S. Virgin Islands, and Grand Cayman, all renowned for their beautiful beaches.
Avoid: A handful of islands, including Dominica, Bonaire, Montserrat, Saba, St. Eustatius, Trinidad, are not known for their beaches.
I love fine dining
If you want great food, you're in luck. Virtually every island has at least a few excellent restaurants, though food in the Caribbean is comparatively expensive because most of it has to be imported. But several islands excel in their dining offerings. Three islands in particular—Anguilla, St. Barthélemy, and Barbados—have a wide variety of excellent restaurants; just be prepared with your platinum card when you get the bill. St. Maarten/St. Martin has a wide variety of restaurants in every price range, though many of the best can be found on the French side in Grand Case.
Avoid: Montserrat, St. Eustatius, St. Vincent, and the Dominican Republic; the first three islands have few upscale restaurants, and in the D.R. the prevalence of all-inclusive resorts means few off-site opportunities except in Santo Domingo and a handful of other places.
I love scuba diving
If you are more interested in what's below the waves than what's above, there are some islands that will definitely appeal to you. Bonaire is one of the best dive destinations in the world, let alone the Caribbean. The Turks & Caicos, Cayman Islands, St. Lucia, and Saba are also renowned for their diving. Dominica is an often overlooked dive destination, as is St. Eustatius, though the latter has some of the best wreck-diving you'll find. And if you like wrecks, the British Virgin Islands has one of the most popular wreck dives in the world, the RMS Rhone.
Avoid: Anguilla, Antigua, Barbados; almost every island has some nearby reef, but these three destinations aren't the best for serious divers.
I love snorkeling
If you're not a diver, you may still have an interest in what's below the waves. Bonaire is great for both since its reefs are just offshore. And the Grenadines (especially the Tobago Cays) and Turks & Caicos are also great for both divers and snorkelers. Other islands, such as Virgin Gorda and St. John, are better for snorkelers.
Avoid: The north coasts of Puerto Rico and Dominican Republic (and also Punta Cana); with no barrier reefs, these waters aren't conducive to clear views or a lot of brightly colored fish.
I love golf
One of the great joys of golf in the Caribbean is the chance to play under the palm trees with a view of the ocean. Some of the best resort courses you'll find at in the Caribbean. Barbados has some excellent (albeit pricey) courses. The Dominican Republic has so many great courses that they are hard to count; so does Jamaica. Nevis has but one golf course (at the Four Seasons), but it's one of the Caribbean's best; the same is true for Palm Island in the Grenadines. Puerto Rico has a wide range of courses, both great and not so great.
Avoid: Bonaire, the British Virgin Islands, Dominica, Saba, St. Barthélemy, St. Eustatius, St. Vincent. Why? No courses. And forget about St. Maarten, too; yes, there's one course, but it's not well-maintained and not really worth your time.
I love nightlife
For those who want to drink and dance the night away, Aruba, St. Maarten, and Puerto Rico are good choices, and all three of these islands also have great casinos. While it has no big casinos, Jamaica does have great nightlife, especially in Negril and Montego Bay. But Trinidad is another island with great nightlife, and Grand Cayman is surprisingly lively after dark. There's a lot to do in the Dominican Republic after dark, especially if you're in the busy capital, Santo Domingo.
Avoid: Montserrat, St. Kits, Saba, and St. Vincent & the Grenadines; every island has something to do after dark, but true night owls will want to look elsewhere.
I love big, all-inclusive resorts
If you like everything in one package, then the two best values in the Caribbean are Jamaica and the Dominican Republic. No other island excels at the AI-resort game quite as well as these two. But St. Lucia has a lot to offer, as does Antigua. But you can't exclude Mexico from your search if you are looking for AI resorts. Cancún, Cozumel, and the Riviera Maya have some of the best and biggest resorts, and the prices there can't be beat.
Avoid: Many islands, including Anguilla, Bonaire, the U.S. Virgin Islands, Puerto Rico, the Cayman Islands, Dominica, St. Barthélemy, and others, simply do not have any all-inclusive resorts.
If you still aren't sure what island is best for you, try out our Travel Planner. Enter all your likes and dislikes and see what destinations show up as your Best Match.