Kingston
Dub Club is the house party that's become a major Kingston brand. And what a house! Set high on Jack's Hill, it looks down over the lights of the city,…
Must-see nightlife in Caribbean
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Habana Vieja
More stylish man-about-town than vain popinjay, El Dandy is an unpretentious cafe by day and a cool cocktail bar by night. A casual greeter shakes your…
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San Juan
This iconic hotel's three lobby bars are undeniably the most glamorous in town, with acres of gleaming marble and lashings of art deco elegance. Choose…
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San Juan
Set up by award-winning Puerto Rican barista Abner Roldán, this contemporary cafe wouldn’t look out of place in New York or London. Supporting the island…
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San Juan
Condado’s most historic hotel has a suitably opulent lobby bar. The master mixologists craft classic and one-of-a-kind cocktails, partnered with some…
San Juan
Santurce's famous market – La Placita – is also the hub of one of San Juan's hottest nightlife scenes. Especially good on Thursday and Friday nights, the…
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Kingston
One of Jamaica's most exciting social enterprise businesses, Deaf Can! operate this cafe to increase opportunities and visibility for Jamaica's deaf…
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Santo Domingo
This fashionable cafe, art gallery, bookstore and cinema is housed within the charming former abode of Emilio Rodríguez Demorizi, one of the Dominican…
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Anguilla
Legendary reggae star Bankie Banx transformed huge piles of driftwood and old boats into what's essentially a giant tree house on the beach. Phenomenal…
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Habana Vieja
From a 2nd-floor balcony, high above the architectural beauty contest that is Plaza Vieja, there’s no better place in Cuba to savor a piña colada than…
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St Vincent & the Grenadines
Managed by the Mustique Company, famous Basil’s has undergone a major overhaul – how you spend US$6 million renovating open-aired, thatched roof huts is…
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Tortola
The most buzzing beach bar on Tortola is ready-made for your Instagram account, with swings in the sea and an 'I heart BVI' sign on land. Paradise lights…
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Habana Vieja
'Aqui jamás estuvo Hemingway' (Hemingway was never here) reads the sign outside Chanchullero, with more than a hint of irony. It's a key point. Since the…
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Bonaire
Bonaire's pretty people seem to have chosen this relatively new double-decker beach bar as their natural habitat – throughout the day they can be spotted…
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Havana
There are a lot of seriously weird (in a good way) places to drink coffee in Havana, but Café Fortuna Joe stands alone, mainly because of its original…
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Varadero
The best coffee in Cuba outside Havana is ignored by most of Varadero's tourists simply because they don't know about it. The reason: this open-all-hours…
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Matanzas
Matanzas has recently made a giant leap into a new artistic domain, thanks largely to places like this smart cafe-cum-art-collective on riverside Calle…
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Trinidad
While other restaurants send their waitstaff out into the street to fish for customers, La Botija crams half the town into its lively corner bar without…
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Santiago de Cuba
Slip up to the 5th-floor roof of Casa Granda for the most breathtaking sunset in Cuba. Views of the scene in Parque Céspedes and the dramatically lit…
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Anguilla
No shirt and no shoes still gets you service at this funky been-here-forever (since the '80s!) beach shack where Johnno's 'famous rum punch,' piña coladas…
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St John
St John Brewers makes its sunny, citrusy suds here. Join locals hanging off the barstools and sip a flagship Mango Pale Ale, or try the alcohol-free…
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Santo Domingo
The dissidence, though pleasurable, couldn't be more extreme here, sipping rum-based cocktails on an astroturfed 3rd floor directly across the street from…
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St-Martin & Sint Maarten
Casual and boisterous, the Blue Martini serves French Caribbean bites but is really more the perfect end-of-day destination for quick mood enhancers or…
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St-Barthélemy
Plastered in a pirate's chest of photos, T-shirts and other detritus collected during many a drunken night since 1949, Le Select is your quintessential…
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Las Terrenas
The hottest bar in Las Terrenas by a landslide, this open-air lounge is a good-time juxtaposition of rustic lounge furniture, fairy-light-lit trees,…
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Punta Cana & the Southeast
The road past mostly undeveloped plots earmarked for suburban-like developments ends rather surprisingly at this raucous and happening two-story…
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St John
Just when you begin to lament the lack of cultural spaces in the USVI you find a place like Bajo El Sol, which showcases local painters, potters and…
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Negril
You’ll be joining the touristy throng at this ever-popular West End institution, but why not? Just for one evening. The drinks menu features empty-your…
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British Virgin Islands
Calypso singer Foxy Callwood single-handedly put Jost on the map with this legendary beach bar. He has his own rum distillery on-site, so fresh booze…
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British Virgin Islands
The Soggy Dollar takes its name from sailors swimming ashore to spend wet bills. It's also the bar that invented the Painkiller, the BVI's delicious-yet…
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US Virgin Islands
Who makes vodka in the Caribbean? Two Virgin Islander brothers who were fed up with all the rum-guzzling pirate stereotypes. At their new bar, which at…
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San Juan
Hiding in plain sight just off the Placita de Santurce, this chilled bar boasts mixologists who craft killer cocktails, such as the adios pantolones …
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St Croix
One of the hippest, sexiest and most urbane spots on St Croix, with a refreshingly high ratio of islanders to tourists. Let the bartender craft a cocktail…
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Anguilla
Dedicated rum lovers should not skip this sophisticated bar wallowing in clubby coziness thanks to dark wood and heavy chairs draped in brown leather and…
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US Virgin Islands
This brewery is indeed micro: it's only open a few days a week, it only brews five beers, and they're only on tap here and at eight island restaurants…
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Santo Domingo
At the entrance, guests step into a shoe shop where artisans craft espadrilles. Continuing to the back, though, the store opens into a trendy cafe with…
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Vieques
For a slice of urban chic at the end of the laid-back Esperanza strip, head to the rooftop bar at El Blok, the island's hippest watering hole. The…
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Nassau
The unmissable nightly Fish Fry is certainly not just about eating. Sky-juice trailers, wooden beer shacks and more substantial establishments keep…
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St Croix
Right on the boardwalk overlooking yachts bobbing in the sea, this open-air brewpub is primo for sampling the small-batch suds cooked up steps away from…
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Negril
Swing by this beach bar run by former Drifters singer Luddy for the terrific reggae and soul jam on Friday afternoons, or live tunes on Sunday – or enter…
