Check the cost of living. Don’t just look at the cost of airfare; dig deeper to see which islands are less expensive once you’re there. The Dominican Republic has some of the region’s lowest hotel and resort rates, while a place like St. Barth’s, known for upscale tourism, will be harder on your wallet. Keep in mind that some less developed islands that are a little harder to get to may make up for the higher airfare with lower costs for lodging and food.