Why go: Anguilla’s silvery sands are legendary. Even though the island only stretches across 16 miles, it’s home to 33 beaches. Shoal Bay East is a traveler favorite thanks to the convenient on-site equipment rental, but if you’re hoping to avoid the crowds, head to Rendezvous Bay instead.
Why go: Choices, choices. These British isles have gorgeous shores to hike on (The Baths), sleep on (Smuggler’s Cove), eat on (Cane Garden Bay) and party on (Jost Van Dyke’s Great Harbour during Old Year’s Night). Plan your beach visits around your mood.
Why go: Grace Bay on Providenciales is one of those “do-everything” beaches, complete with crystalline water, powdery sand, a colorful coral reef and a variety of restaurants. If you can’t secure an umbrella here, try Governor’s Beach or Pillory Beach.
Why go: If you travel to the U.S. Virgin Islands, you can’t skip a visit to Magens Bay. St. Thomas’ most famous shore is too beautiful for words, but be prepared to share the scenery with dozens of fellow tourists. To avoid the crowds, sail to the quieter St. John, home to Trunk Bay
Why go: It’s hard to top Grand Cayman’s Seven Mile Beach — the chalky sand and warm waves are nothing short of spectacular. There are other enviable banks along the Cayman Islands, but why bother going somewhere else when this stretch is so good?
The charming Cayman Islands continue to be a coveted Caribbean getaway for both adventurous and more immobile travelers. Gorgeous barrier reefs call to divers as the rum punch calls to the beach bums. Honeymooners hike through the 200-year-old Mastic Trailas parents take their children for interactive swims at Stingray City. Whichever way you choose to mellow out, the Cayman Islands can oblige.
The Cayman Islands are an archipelago of three islands, lying 90 miles south of Cuba. The largest, Grand Cayman, is full of gargantuan resorts with all-inclusive options, perfect for those who prefer pre-planned itineraries and don’t mind sharing the sights with cruise crowds. For freewheeling vacationers, the less-traveled Cayman Brac and Little Cayman offer some of the best diving in the Caribbean.
Why go: You can pack light for St. Martin-St. Maarten: Along some shores, you may only need sunglasses. Ravishing Orient Bay and Cupecoy Beach are popular with nude sunbathers. For a more modest experience, watch planes land at Maho Bay or attend a bonfire at Friar’s Bay.