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You can’t really blame Americans for not knowing one Caribbean island from another. Our first exposure to them was likely the animatronic pirates firing fake canons at Disneyland. Or, if you’re a little younger, Johnny Depp! Either way, “the Caribbean” to many Americans is simply a collection of islands somewhere south of Florida; and you’d be hard-pressed to find somebody who knows the difference between the Greater and Lesser Antilles, much less where they are located. And it’s a shame, really. Because while every island down there boasts turquoise water, white sand beaches, and a lot of rum, that’s pretty much where the similarities end. Which is why, in the name of education, civic duty, and better vacation planning, we’ve put together this handy guide to what makes each of the 29 islands special.

NOTE: Round-trip airfare is calculated from JFK for a random week in May.


British Overseas Territory
Capital: The Valley
Average RT airfare from US: $552
Why visit? Every bit as beautiful as its Leeward Island neighbors, Anguilla has remained relatively untouched by mega-resorts and casinos – meaning the vast stretches of perfect beach aren’t too crowded, and you’ll enjoy a more remote Caribbean experience.

Antigua and Barbuda

Independent (UK, 1981)
Capital: St. John’s, Antigua
Average RT airfare from US: $350
Why visit? There are two distinct experiences you can have on these islands: Antigua is more of the traditional Caribbean paradise complete with tropical rainforest; Barbuda, on the other hand, is all about the fantastic wildlife, including a bird sanctuary, native deer, and deep-sea fishing.


Sovereign State, Kingdom of the Netherlands
Capital: Oranjestad
Average RT airfare from US: $440
Why visit? Nature is the main draw here. The perpetual sunshine and lack of precipitation creates some spectacular inland desertscapes to complement the over seven miles of white sand beaches — including Palm Beach, one of the best beaches in the Caribbean.

The Bahamas

Independent (UK, 1973)
Capital: Nassau
Average RT airfare from the US: $350
Islands included: There of 700 of them in this flat-island chain; the most visited are Abaco, Bimini, Eleuthera, Exuma, Grand Bahama, Nassau, New Providence, and Inagua.
Why visit? It’s the closest Caribbean country to the United States and a key stop on a lot of cruises. But past the straw markets and hair braiders, the Bahamas boast one of the best pink sand beaches in the world at Harbour Island, swimming with feral pigs, and the Atlantis resort if you’re looking for a little bit of Vegas in the Caribbean.


Independent (UK, 1966)
Capital: Bridgetown
Average RT airfare from US: $443
Why visit? Carnival, done to celebrate the end of Crop-Over, is sort of like the Bajan Thanksgiving. Except instead of stuffing themselves with food and laying on a couch, people dress up in colorful costumes and dance in parades throughout the island. Check it out from June until the first week of August.


Special Municipality of the Netherlands
Capital: Kralendijk
Average RT airfare from US: $575
Islands included: Bonaire and Klein Bonaire
Why visit: Bonaire is a quirky little island in between its two better-known cousins. The night diving is some of best in the world; using UV lights, you’ll spy spectacular underwater marine life.

British Virgin Islands

British Overseas Territory
Capital: Road Town, Tortola
Average RT airfare from US: $618
Islands included: The BVI comprises 60 islands, including Anegada, Jost Van Dyke, Tortola, and Virgin Gorda
Why visit? Even if you’re not going for Yacht Week, the BVI are a top destination for boaters from around the globe. And that kind of money lends itself to some spectacular private-island resorts, like the Bitter End Yacht Club and Cooper Island.

Cayman Islands

British Overseas Territory
Capital: George Town, Grand Cayman
Average RT airfare from US: $400
Island included: Grand Cayman, Little Cayman, and Cayman Brac
Why visit? Though technically the Cayman Islands aren’t part of the Greater Antilles, they lie in the same geographic region. The islands’ reputation as a hub for offshore banking has helped lure a lot of big-time chefs drawn to big-time money. Miami’s Cindy Hutson and New York’s Eric Ripert of Le Bernadin have both opened restaurants in the past few years, and other big names in food are following.


Sovereign State of the Netherlands
Capital: Willemstad
Average RT airfare from US: $460
Why visit? Curacao offers some of the most diverse culture in the Caribbean, including the oldest synagogue in the Western Hemisphere. The main harbor is also a UNESCO World Heritage Site.

Dominican Republic

Independent (1863, Spain)
Capital: Santo Domingo
Average RT airfare from US: $325
Why visit? The beaches in the Dominican Republic have become the big draw in the past decade. But it’s also a country of over ten million people and the capital city of Santo Domingo is a vibrant, exciting, historic spot to visit when the sand gets old. The cigars are as good as any in Cuba, and you can pretty much see a future MLB player if you catch a Dominican League baseball game while you’re there.


Independent (1974, UK)
Capital: St. George’s
Average RT airfare from US: $530
Islands included: Grenada, Carriacou, Petit Martinique, Ronde Island, Caille Island, Diamond Island, Large Island, Saline Island, and Frigate Island
Why visit? Though many people know it only as “that place we invaded in 1983” and “where British Airways accidentally sends people trying to go to Granada,” the more-traditional nickname is the “Spice Islands.” That name comes mostly from Grenada’s abundance of nutmeg, which is best sampled in its famous sweet potato pudding.


Independent (1962, UK)
Capital: Kingston
Average RT airfare from US: $435
Why visit? Obviously, if you’re into reggae music; but even if Bob Marley isn’t your jam, there are the beaches of Negril and their famous cliff divers. Also, two spots in Jamaica fall on our list of cheapest Caribbean paradises.

Puerto Rico

U.S. Territory
Capital: San Juan
Average RT airfare from US: $469
Islands included: Vieques, Culebra, Mona, Desecheo, and Caja de Muertos are also part of Puerto Rico
Why visit? Traveling to Puerto Rico is like visiting a foreign country, but without leaving the US. Experiencing the country’s Spanish Caribbean culture, food, and music is an easy way to dip your toes into Latin America if you’ve never been, and the beaches at Vieques and Culebra are some of the region’s hottest new destinations of the past ten years.

Saint-Barthélemy (aka St. Bart’s or Saint-Barth)

Destination Wedding Honeymoon Destination St. BarthOverseas Collectivity of France
Capital: Gustavia, Saint Barthelemy
Average RT airfare from US: $900
Islands included: Saint Barthelemy, Île Chevreau, Île Frégate, Île Toc Vers, Île Tortue, Gros Îlets, and Île Fourchue
Why visit? It’s known as “The Hamptons of the Caribbean,” mostly because it’s a weekend escape for wealthy New Yorkers and celebrities. Who knows, on some Fridays it’s probably even quicker to get to.

Saint Kitts & Nevis

Independent (UK, 1983)
Capital: Basseterre, Saint Kitts
Average RT airfare from US: $625
Why visit? The black sand beaches at St. Kitts — both islands are volcanic mountains and the ancient eruptions gave the island one of the largest concentrations of them in the world.

Saint Lucia

Independent (UK, 1979)
Capital: Castries
Average RT airfare from US: $450
Why visit? The Piton Mountains, where you can not only visit seemingly-remote villages, but also drive right up an active volcano.

Saint Martin/Sint Maarten

Destination Wedding Honeymoon Destination St. Martin Sint MaartenOverseas collectivity of France/ Constituent country of The Netherlands
Capitals: Marigot/Philipsburg
Average RT airfare from US: $488
Why visit? Aside from taking videos of yourself getting blown back by a 747 while you lie on the beach? Plenty. This island is controlled by the French and the Dutch, so you’ll experience both cultures without having to go more than a few miles. Much less across an ocean.

Saint Vincent and the Grenadines

Independent (UK, 1979)
Capital: Kingstown, St. Vincent
Average RT airfare from US: $530
Islands included: St. Vincent and the Grenadines comprises 32 islands, nine of which are populated
Why visit? Next to the BVI, St. Vincent is the Caribbean’s top destination for yachters. Also, medical students — it’s home to three medical schools with direct ties to the States.

Turks & Caicos Islands

British Overseas Territory
Capital: Cockburn Town, Grand Turk
Average RT airfare from US: $475
Islands included: There are 300 islands between the Turks & Caicos. The most populated ones include Grand Turk and Salt Cay in the Turks Islands, and Providenciales, Parrot Cay, North, East, South, West and Middle Caicos in the Caicos.
Why visit? It might offer the most turquoise water of any spot in the Caribbean, and the snorkeling at Coral Gardens in Providenciales is top notch. Also, if you hit the Da Conch Shack in Provo, the staff will actually dive in the water and catch your conch fritters.

US Virgin Islands

US Territory
Capital: Charlotte Amalie, St. Thomas
Average RT airfare from US: $380
Islands included: St. Croix, St. John, and St. Thomas
Why visit? It’s the most Caribbean place you can go without needing a passport. You get the natural beauty and exotic feel of the islands, but with American infrastructure and nonstop flights. Somehow, though, the culture remains relatively untouched by America — so all the better.