Soggy Dollar, Jost Van Dyke

The most legendary bar in the Caribbean's most legendary yacht charter mooring, this British Virgin Islands hotspot draws a sauced, swimsuit-clad crowd with its habit-forming Painkiller cocktails. Sip one in a hammock overlooking the broad beach at White Bay or slip into the electric blue water with a plastic cup. There were no roads accessing this place back in the seventies, when the Soggy Dollar first opened, when boaters began making landfall with sodden bills in their pockets. Little has changed since then, as sailing-types continue to dominate the boozy scene. 

Feet from water: 30
The regulars: Deeply tanned sailors and nervous bareboat charterers who haven't gotten their sea legs.
What to order: The Painkiller, made with local Pusser's rum, cream of coconut, pineapple, and orange juice then topped with shaved nutmeg.