From archetypal thatched huts with driftwood benches to chic waterside lounges on docks, T+L has found the silands' superlative spots for outdoor evenings.
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.