Anguilla

At the top of the Leeward Islands, Anguilla embodies a particular vision of the Caribbean. The caliber of its sun-kissed beaches, and the fact that the island (and its associated cays) hasn’t been completely ransacked by development, draw the rich and famous—musicians, movie stars, politicians, corporate bigwigs—here in numbers disproportionate to the unassuming size of this British overseas territory. While Anguilla’s a pricey destination, some of its richest attractions don’t cost an arm and a leg to enjoy.

The 30-odd beaches of Anguilla well represent the Caribbean ideal, and as swanky as the resorts can be that edge them, all are open to the public. The azure waters are soothing enough simply to appreciate, drowsily, from a beach towel or a seaside bar stool, but it’s unlikely you’ll be able to resist getting a little wet here. Snorkelers get an easy and accessible taste for Anguilla’s undersea life in sheltered waters such as Crocus Bay and Junk’s Hole, while divers can explore deeper reefs and a host of shipwrecks—including the 18th-century ruins of the Spanish galleon El Buen Consejo in the Stoney Bay Marine Park. The island’s also a premier spot for sailing, kitesurfing, and saltwater fishing.

An Anguillan escape completely devoted to beachfront R&R is all well and good, but there's a fascinating cultural heritage to appreciate, too. Some of the Caribbean’s standout archaeological sites, including the amazing Taino petroglyphs and stalagmite carvings of Fountain Cavern, offer insight into the island’s long-vanished Amerindian lifeways. More recent history dominated by European colonialism—mostly a British story—is revealed at landmarks such as the Wallblake House (a 1787 plantation home in Anguilla’s capital, The Valley) and the Old Salt Factory and Pump House at Sandy Ground. Anguilla’s also a fantastic place to eat on account of its strikingly multicultural cuisine—with West Indian, African, and European influences all knotting together—and a plethora of international restaurants catering to the luxury-tourism market.

An escape to Anguilla makes for one sort of archetypal Caribbean experience if you want to compete with the superstars and spend an awful lot of money. But—if you’re savvy—you can also soak up some of the territory's Antillean magic without breaking the bank.