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Caribbean Bars I Need to Drink In

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Hemingway, pirates and rum
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Avenida Paseo y, Calle 1ra, La Habana, Cuba
With the US travel restrictions to Cuba recently relaxed, I was able to realize a lifelong dream and visit that enchanting tropical isle under an official educational license for "people to people" travel. There were so many highlights, I'll never...
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Negril, Jamaica
No hotel in Jamaica blends better with its surroundings than the aptly named Rockhouse, a string of villas clinging to the top of a sea cliff at the western tip of the island. Local stone, timber, and thatch are the building materials, and a...
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Pointe du Bout, Les Trois-Îlets 97229, Martinique
This iconic bar sits on stilts above the sea at the Hotel Bakoua in the sultry resort area of Trois-Ilets, just across the Bay of Fort-de-France from the island’s capital city. People don’t come here for the drinks (stronger and better...
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Lighthouse Road, West End, Negril ., Jamaica
Built on the edge of limestone cliffs, this secluded resort features 12 charming rooms, all of which have ocean views. Guests can dine on authentic Jamaican cuisine in a private grotto, or take in the scene at the candlelit Cave Rum and...
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British Virgin Islands
This family-run restaurant serves up some of the best conch fritters in the Caribbean. The relaxed vibe and plastic chairs make for an unusual place for a romantic dinner, but just add a sunset and a perfectly prepared lobster, and Cow Wreck...
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Obispo, La Habana, Cuba
and he might even have slept here- this place is world famous for two things - its Hemingway connection (Papa still resides in the corner of the bar in a life sized bronze) and it is reputed to be the home of the original daiquiri. what I can say...
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Henrys, Bridgetown, Barbados
There's simply no better place to get Caribbean spiny lobster on Barbados than Lobster Alive. Fact. Why? Because practically every lobster sold in every restaurant on the island comes through this one unassuming location. The problem is that due...
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Black River, Jamaica

From Jamaica's Treasure Beach, on the island's southwestern coast, we hired a local boat owner to zoom us a few miles north to the Pelican Bar (pictured). About a mile offshore, the Pelican sits on stilts on a sandbar in the Caribbean Sea. The...

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153 Obispo, La Habana, Cuba
Stop by the Ambos Mundos Hotel in Old Havana. Ernest Hemingway spent many years living in a hotel room here and the view from the rooftop restaurant and bar is breathtaking. Have a cool, refreshing mojito after visiting the small Hemingway museum...
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The first thing you notice when you sidle up to the approximately eight foot bar (that’s pretty much all there is to Mojito Bar, besides some chairs on the beach) are the melons. The pineapples. The oranges, papaya, watermelons and more—all...
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SURFER'S BAY - MOONRAKER, GREEN GARDEN, LANDSDOWN, SILVER SANDS, Barbados
Luckily Surfer’s Bay Beach Bar isn’t exclusive to those with a penchant for getting tubed, pulling aerials or catching the perfect wave. All you need is a laid-back vibe and you’ll fit in perfectly at this idyllic beach bar on the southernmost tip...