Anguilla

Anguilla is a Caribbean British overseas territory. It's one of the Lesser Antilles' most northerly Leeward Islands, located east of Puerto Rico and the Virgin Islands and straight north of Saint Martin. The main island of Anguilla, which is roughly 16 miles (26 kilometers) long and 3 miles (5 kilometers) broad at its widest point, is part of the territory, as are a number of many smaller islands and cays with no permanent population.

On Anguilla, you'll discover something a little more authentic than on some Caribbean islands masquerading as tourist traps. Cruise ships, casinos, and high-rise hotels are prohibited, but there are plenty of beautiful, coral-filled waterways, unmarked and gravel roads, and low-key beachside houses. From extravagant resorts to smart outdoor eating, pampering is in high demand. The days here are long because there isn't much to do but rest. However, as the sun sets, you'll be treated to one of the greatest live music scenes in the Western Hemisphere. Quincy Jones, Bankie Banx, and Jimmy Buffett have all performed on Anguilla's pristine beaches.