Sweet Spot: Soggy Dollar Bar

Island: Jost Van Dyke

It was once accessible only by water (there's now a rough road, though most visitors still arrive by boat), so thirsty sailors would brave the waters to make it ashore, and pay with wet, disintegrating bills. They were likely on a pilgrimage to the birthplace of The Painkiller, a dangerous cocktail that proliferated in the area as speedily as the plant for which it's named. Lunch is perennially busy, but things simmer down come evening. Order the conch fritters and roti—a local favorite of flatbread topped with curry chicken—and prime yourself for competition. In these parts, Blackbeard is said to have played "get the ring on the hook" using hemp and bones; today, gamers at the Soggy Dollar vie to finesse a steel ring-on-a-string onto a nail.

Days lunch is served: 365

Meal Ticket: Entrées, $7–$33

Vibe: Strings of signal flags from visiting yachts establish a castaway mood

On-Site Guest Rooms: 6

Tech Quirk: The Web site, soggydollar.com, has a live cam, so you can preview the scene

Contact: 284-495-9888

*27: typical number of swim strokes to reach shore

Next: Stanley's Welcome Bar >

Photograph by Julien Capmeil for Condé Nast Traveler