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Caribbean 101

The definitive guide to choosing an island

By ShermansTravel Editorial Staff

Updated on April 2nd, 2013

When winter gets underway, many of us start dreaming of a Caribbean vacation. The region's appeal is undeniable: Swaying palm trees, swaths of beach, turquoise waters, and great nightlife are just some of the islands' draws. But knowing you want to hit the beach and choosing which island to visit are two different matters. Considering the region is home to hundreds of islands, many with incredibly different personalities and offerings, first-timers are easily confounded by the array of choices, and even return visitors can make mistakes. Our Caribbean 101 Spotlight is meant to help you decide which island suits you best – whether you're heading south for the first time, or the hundredth.

We've reviewed 23 of the most popular islands below, and broken them down into seven categories so you can most easily browse based on your interests. After all, if all you want is a beach vacation, there's no point considering islands that don't have any (indeed, while it may come as a surprise to some, many Caribbean islands lack beaches of note). Some of our top islands fall into several categories (their varied offerings usually make up a large part of their appeal).

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