Anguilla

Anguilla is one of the premier vacation spots in the Caribbean. A British overseas territory east of Puerto Rico and the U.S. and British Virgin Islands, the island encompasses a total of 35 square miles and has a population of just over 14,000. The average temperature in Anguilla is 80 degrees and northeastern trade winds keep the island cool and dry. September and October tend to be rainier than other months while February and March are generally drier

The most exciting thing about Antigua and Barbuda isn't its geography; it's the fact that you can visit Mt. Obama—a mountain named after former president Barack Obama—and take in some breathtaking views of this tropical paradise. If that isn't enough, there's also Princess Diana Beach on Antigua (named in honor of Princess Diana’s visit to the beach shortly before her tragic passing).