Many know Jost Van Dyke, one of the handful of inhabited islands in the BVIs, as the barefoot island. Fifteen years ago, it had no electricity and few paved roads. That's changed, but the atmosphere hasn't. There are still no brand-name hotels—stay at White Bay Villas, which offers essential amenities like iPod docks and charcoal grills (from $135). Then start with the adventure: rent 12- or 13-foot SUPs from Jost Van Dyke Scuba, then head into Great Harbor to paddle near surfacing dolphins ($20 per hour). But take the island's nickname to heart and spend some time padding between the 50-odd seasonal bars.
The Soggy Dollar, located on White Bay, claims invention of the Painkiller (rum, pineapple juice, OJ, cream of coconut) and serves four-course dinners to the yachting set; Foxy's Taboo boasts one of the biggest Caribbean New Year's Eve parties in Great Harbor; and Ivan's Stress Free does barbecue every Thursday—and offers campsites for the inevitable postprandial collapse (equipped sites from $45).
Access: Fly to St. Thomas directly from the East Coast, and charter a boat to Jost—or take the 75-minute public ferry from Red Hook, which is 25 minutes by cab from the airport.