Road Bay, Anguilla
Thirty-three gorgeous white-sand beaches fringe the shores of Anguilla, a British Overseas Territory and northernmost of the Leeward Islands in the Lesser Antilles chain. Anguilla was first settled around 3,500 years ago by Amerindians, including the Arawak (or Taino) and Carib peoples; British colonists claimed it for the Crown in 1650, growing tobacco and cotton before bringing enslaved Africans to cultivate sugarcane on vast estates. Today, the island’s economy relies mostly on tourists lured by those silky sands and year-round temps averaging 84 degrees Fahrenheit. Road Bay — Anguilla’s main port and harbor — shelters the small village of Sandy Ground and its wide beach lined with colorful bar shacks and restaurants. You could spend the whole day here, snorkeling with sea turtles or catching the boat tender to Sandy Island, an idyllic little islet located just off shore. Head a few miles inland to visit Wallblake House, a well-preserved plantation home from the late-1700s; or further north to Shoal Bay to explore Fountain Cavern National Park with its ancient Arawak rock art and relax on one of the top-ranked beaches in the entire Caribbean.