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With sinfully sunny beaches, jade-green mountains, and a star-studded past (in the '50s and '60s, it entertained a cast of Hollywood characters such as Errol Flynn and Elizabeth Taylor), the island possesses a chilled-out vibe that's often imitated but never duplicated. As one of the Caribbean's most northwestern spots, it’s a quick flight away -- two at most. And though you'll probably want to hang out forever, you can get a good feel for it in four or five days.
Where to start: Frenchman's Cove, shown here, often tops Jamaica's "best beach" lists.
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Where to Stay
Soak up all that silver-screen glamour at GoldenEye, on the northeast coast. Originally the pad of James Bond creator Ian Fleming, who frequently had the glitterati over to party, it's now a hotel owned by Chris Blackwell, the Jamaica-bred music mogul behind legends like Bob Marley and U2. The Fleming Villa, shown here, still holds the famed author's writing desk.
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The Bar Scene
Spend an evening at Geejam Hotel's Bush Bar where you can grab dinner—the kitchen serves an upscale take on regional favorites—and catch a good local band.
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One group you'll find at the Bush Bar: The Jolly Boys, a hip band of septuagenarians dressed to the nines in fedoras and leisure suits, who are repped by the former head of Island Jamaica records. Their specialty? Mento, a folk style considered "the grandpappy of reggae". They do a mean rendition of Amy Winehouse's "Rehab," so don't forget to request it.
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You don't have to go far from your cozy digs to get active island-style. You can paddleboard around the lagoon next to the GoldenEye.
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Worth the Ferry
Though the rest of your time will probably be split between a sandy strand of coast and a roadside jerk stand like Scotchie's, you can't go home without a trip to Floyd's Pelican Bar, built on stilts out in the bay off Parottee Beach. The bartender will cook up a nice meal and keep a beer in your hand as you wade in the shallow water. No shirt, no shoes, no problem.
Here, fishermen wait on Parottee Beach to ferry people out to Floyd's for lunch, dinner, or drinks. The cost? About 10 bucks per person each way.
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Plan Your Trip
When to Go
Stick to late April through July, which is technically low season (cheaper rates, yay!), but before the worst of hurricane weather hits in August and September.
How to Get There
Fly into Montego Bay, then arrange for a hotel transfer for the 90-minute drive to GoldenEye.