Anguilla Built in the sand dunes of Rendezvous Bay along the island’s West End, Anguillan reggae icon Bankie Banx’s Dune Preserve (Rendezvous Bay; 264/729-4215)—made of driftwood and washed-up ships, with live music and a dance floor—is always a scene.

Dominican Republic The island’s sophisticated set can be found at the unmarked Aura Beach House (Guayacanes, Juan Dolio; 809/526-2319) sipping clericot (white sangria) and lounging on varnished pine canopy beds at the water’s edge.

St. Kitts After a day of snorkeling in coral reefs along the island’s southeastern tip, drop by the Turtle Beach Bar & Grill (Southeastern Peninsula; 869/469-9086) to swing in a hammock under a palm tree, mango colada in hand, as you gaze out across the Atlantic at Nevis.

Turks and Caicos If you think Turks and Caicos is short on after-dark spots, head to Grace Bay Club’s new Infiniti Bar (649/946-5050; gracebayclub.com), from the designer of Nobu London: the black marble bar stretches from the hotel’s palapa restaurant all the way to the shore.

Vieques Come late afternoon, in-the-know travelers wander right from the nearby ferry landing to Al’s Mar Azul (577 Rickenhoss, Isabel Segunda; 787/741-3400)—a laid-back, open-air bungalow—to drink margaritas and watch the sunset while casting for silvery tarpon off the deck with locals.