Port Antonio, Jamaica
Jamaica has an image problem: It's either college girls raging bachelorette-style in Montego Bay or that dude from work coming back from Negril with a fucking braid in his hair. But there's a whole other Jamaica out there, as long as you're willing to put in a little effort.
Here's how: Just a couple of hours from Kingston, along the island's prettiest mountain roads, is a wild, resort-free slice of tropical perfection called Port Antonio. One of its beaches, Frenchman's Cove, was used for the country's classic travel-agency posters; another, the Blue Lagoon, is where a pubescent Brooke Shields went all feral-sexy.
Villas built by an early jet-set crew that included Errol Flynn and Ian Fleming – and which have been converted into budget guesthouses and superluxe rentals – dot the hillside. The most original stay is hotel-and-recording-studio Geejam. But even with all its international influence, Port Antonio is a real Jamaican town. Bike to the beach or to the spliff-and-dancehall-fueled Roof Club (11 West St, 876-715-5281), full of locals and blissed-out expats. For jerk chicken, it's Boston Bay; for reggae, get down at one of the sonic boom sound-system parties.
More information: Fly to Kingston and drive two hours northeast. Geejam's villas are set into the rugged hills. [From $495; geejamhotel.com]