In winter, the idea of escaping to a Caribbean island probably occurs to each of us at least once a day—and thanks to increased seasonal flights to the region, it’s never been easier to put that plan into action. The only challenge is deciding where to go. With more than 7,000 individual islands (and 28 different countries), there are lots of wide beaches and shimmering waters to choose from. Here, we do some match-making to help you out.