With no real town and little in the way of nightlife, the Caribbean island of Anguilla—which is just 17 miles long and 3 miles wide—generally attracts those looking to lie low. However, those interested in a bit more action can find it on the island in August, at the conclusion of months of sailing competitions—an Anguillan sporting tradition that dates to the early 1900s. During the races’ final legs, from July 28 through August 11, parties and beachside celebrations are held all over the island. After the day races are finished, nighttime activities such as calypso and soca band competitions, as well as talent and other contests, take place at night.
Some of the best vantage points for watching the races are at the villas at the Viceroy Anguilla. All of the 31 blufftop, oceanfront, and beachfront villas (nightly rates start at $2,250 during July and August) are terraced along the beach to offer stunning views of the ocean. Each of the four- and five-bedroom homes features interiors by Kelly Wearstler, as well as outdoor showers and private plunge pools. Additionally, the resort offers shuttle service to Sandy Ground for the Champion of Champions boat race on Sunday, August 11, and it hosts a boat-race reception on the property’s Ocean Terrace so that guests can enjoy the view while the boats sail by.
Viceroy Anguilla, 264.497.7000, www.viceroyhotelsandresorts.com