Treasure Beach
A thatched hut on stilts, built on a submerged sandbar 1km out to sea after owner Floyd saw it in a dream, is still Jamaica’s – and perhaps the planet’s –…
Must-see nightlife in Caribbean
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,…
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…
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…
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…
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…
Kingston
One of Jamaica's most exciting social enterprise businesses, Deaf Can! operate this cafe to increase opportunities and visibility for Jamaica's deaf…
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…
Vedado
Behold the backlit photo art, the sofa shoehorned into the trunk of an American car, and the globes doubling as lampshades. The Belview, bivouacked in a…
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…
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…
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…
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…
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…
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…
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…
The Abacos
Green Turtle Cay's most beloved bar was badly damaged in Hurricane Dorian but was being rebuilt at the time of writing. That's not surprising as it's been…
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…
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…
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…
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…
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…
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…
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…
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…
Vedado
Art and coffee go together like Fidel and Che in this wonderfully reimagined mansion with an interior that features revolving local art. Seating is…
Sancti Spíritus
It doesn't get more underground than this Cuban-Italian cafe with its easy-to-miss sign. Follow a staircase to this 9th-floor apartment sporting tiny…
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…
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,…
Santa Clara
You can chinwag and neck a cold bottled beer with locals of all types in this legendary dive bar under the porches of the equally legendary Teatro la…
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…
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…
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…
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…
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…
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…
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 …
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…
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…
