There are thousands of islands in the Caribbean. But even if you're a regular to the region, some of its most secluded beaches and waterfront establishments might still remain secret. So we embarked on a fact-finding mission, combing every beach and islet from Anguilla to Tobago, and soliciting every style-savvy Caribbean expert we know. Here, our favorites: 50 must-see spots on your next island getaway.
Little Bay Beach, Anguilla To reach this remote cove, you'll need to hire a boat or climb down 66 feet on the fishnet ladder carefully tied to the bluff's top. The difficult approach is worth the work; you're rewarded with 80 yards of talcum sand, walled in by high cliffs on three sides.
Curtain Bluff, Antigua The wide, golden beach is fringed with palms and mangrove wetlands on one side, water clear enough to see your feet in on the other. The only way to set up camp under one of the private waterfront palapas, though, is to spend a night at the luxurious Curtain Bluff Hotel.
Dos Playa, Aruba Fronting a jagged, limestone coast that's perpetually awash in salty surf, this isolated sliver of sand has rolling dunes and Dr. Seuss—like cacti burrowed into the rocks. Leave your snorkel at the hotel—the waves are too wild for swimming—and watch the wind surfers from the safety of a picnic blanket.
Anegada, British Virgin Islands More than 300 ships have crashed into the sharp reefs surrounding this deceptively tiny islet. The part you see is only 15 miles around. But on the north end's Loblolly Bay, the reef is so close to the crescent-shaped shore that waves are reduced to lapping white foam.
La Sagesse, Grenada A nature preserve at the end of a one-mile, rock-studded road (note the grazing cows), this half-mile of sand curves along a cliff dense with coconut palms. Have lunch at the rustic seaside restaurant, then rummage through booksellers' stalls beneath the almond trees.
Honeymoon Beach, St. John One of seven beaches that make up Caneel Bay, Honeymoon Beach is part of the 5,000-acre Virgin Island National Park. There are no huts or cabanas, just empty stretches and neon-colored coral reefs. Lie on the endless white sand and watch the sailboats—and the world—go by.
Anse Chastanet, St. Lucia Reachable by water taxi (or by an hour's walk along a hilly dirt road from Soufrière), Anse Chastanet has some of the island's best snorkeling. A resort of the same name crawls up just behind the dark-sand beach, its whitewashed guest cottages peeking from the Day-Glo green hillside.
Manzanilla Beach, Trinidad The island's eastern coast is rough enough to deter development, and that keeps this beach free from the masses—well, almost. Roaming water buffalo, herons, and egrets regularly parade down the 17-mile strip of brown sugar—like sand, which is bordered by coconut and mangrove trees.