The keys to a good weekend getaway destination in the Caribbean are simple:
Location: You don't want to spend half of your weekend getaway on a plane, so the best weekend getaways are either close to the U.S. or have quick flight connections -- ideally, three hours or less by air.
Transportation: The more airlines serving your destination, the more flight options you'll have. Popular destinations also have more nonstop service, meaning quicker flight times.
Cost: More competition among airlines usually equals cheaper airfares, especially in markets serviced by low-cost carriers. Ditto for destinations that have multiple resorts vying for your business. You don't want to break the bank for a few days away, even if they are spent basking in the Caribbean sun.