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…
Must-see nightlife in Caribbean
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…
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…
Nassau
The unmissable nightly Fish Fry is certainly not just about eating. Sky-juice trailers, wooden beer shacks and more substantial establishments keep…
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…
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…
Havana
Excellent coffee, fine croissants, suave non-reggaeton music and Charlie Chaplin movies playing on a loop in a scarred Centro Habana apartment – what more…
Rincón
Voted best Caribbean beach bar by USA Today in 2018, Tamboo overlooks some of the best sand in Rincón. Hosts a congenial après-surf scene and a crowd of…
Tortola
This beachside bar-restaurant almost always has a crowd of boozy revelers. It takes its name from owner Quito Rymer, whose band has toured with Ziggy…
Punta Cana & the Southeast
The city's most happening and sophisticated spot, this cocktail bar near the Basilica de Nuestra Señora de la Altagracia does a lethal, vodka-laced…
Bermuda
See that pirate ship by the cruise-ship pier? Not only is it a bar that stages booze cruises and DJ nights, but it's also the place to rent hydrobikes …
Bermuda
High ceilings, striking pieces of contemporary art, cube-like furniture and an innovative cocktail list are the distinguishing features of this popular…
Rincón
This cracking brewpub brings the Plaza de Recreo in central Rincón to life with its stellar selection of Puerto Rican and US ales and lagers. San Juan's…
Port of Spain
First opened as an inexpensive lunch spot, Frankie's has morphed into one of Ariapita Ave's best-loved liming locations. You can still get local lunches …
Bermuda
With low ceilings and dark wood furnishings, at first glance this is a quintessential British pub, only with local microbrews on tap, as well as several…
St Croix
This new craft brewery opened in 2018 in the William Roebuck Industrial Park on the island's south side. Sidle up to the indoor-outdoor bar and order one…
Montego Bay
If you’re into big nightclubs, Pier One is the place to go in Montego Bay. It attracts a largely local crowd, dressed to impress and dancing as if their…
Negril
About as local as it gets, this friendly, dingy neighborhood dive bar is redolent with the scent of di 'erb. Nothing fancy: just cold Red Stripes and…
Bermuda
One of Hamilton's most buzzing places after hours, Cafe Cairo may be deliberately kitsch (the Egyptian decor is unconvincing), but the Middle Eastern food…
Freeport & Lucaya
Down a few winding backroads to the beach east of Lucaya, this funky little timber beach shack is an under-the-radar classic with sandy floor and…
Tobago
Perched on the cliffside above Parlatuvier Bay, this friendly Tobago rum shop is a great place to kick back and enjoy superb views over a beer or a glass…
Rincón
Wall-to-wall suntans and syncopated reggae music pumping out beneath the sun-dappled palm trees; Calypso is everything you’d expect a beachside surfers’…
Tobago
Right on the sand where Pigeon Point Rd forks right, this cool little beach bar serves them cold and mixes a mean rum punch. Great for sunset-watching;…
San Juan
If Hunter S Thompson's ghost wanted to relive his Rum Diary days, this is where you’d find him. Unashamedly crusty, the walls of this cavernous drinking…
Habana Vieja
Live bands rock the rafters, locals knock back powerful CUC$3 mojitos, and earnest travelers banter about Che Guevara's contribution to modern poster art…
Factoria Varadero 43 Cervecería
Varadero
Specializing in large, super-chilled jars of house-brewed beer served a drunken stumble from the beach, La Factoria is related to a similar well…
Havana
This fabulously chilled tapas bar occupying an unsignposted villa in the diplomatic quarter is where hip habaneros come to consume cocktails and art…
Anguilla
Heed the call of the casbah in this Moroccan-themed tent with sultry lighting and cushion-strewn sofas to munch on Mediterranean tapas (US$5 to US$22) and…
Havana
The rooms may have lost their luster, but the Inglaterra’s open-air roof terrace remains one of the best free-entry bars in Havana for live music and…
Barbados
One of the most atmospheric bars on this coast, John Moore is a fantastic place to escape the confines of your hotel and meet some Bajan characters. You…
Willemstad
The island's finest specialty coffee bar is ensconced in one of Pietermaai's restored Dutch colonial homes, with scarlet walls, an old-timey cash register…
Grenada Island
Good craft beer has a home in the Windward Islands. This neat local brewery started out as the house brewery at the True Blue Bay Resort and then expanded…
Santa Clara
You say you want a revolution… Well, Santa Clara's a good place to start. It's already had one, successfully ignited by Che Guevara in 1958. This new cafe…
St-Barthélemy
St-Barth's first traditional wine bar looks like it was plucked from a hip Parisian backstreet and set down here. A timber bookcase-style cabinet of prime…
St Lucia
Sit at the breezy bar overlooking the water at this fantastic little cafe right on the sand at Laborie and enjoy great smoothies, local juices or a cold…
Aruba
An island institution, Charlie's has been serving up cold beers and good times to tourists and locals alike since 1941. The walls are plastered with old…
Havana
In Starbucks-free Havana, every cafe is individual and Siá Kará exhibits its character with graffiti-covered tables, an old tie collection and a parody of…
Vedado
Vedado flirts with bohemia in this dimly lit gay-friendly bar that might have materialized from Paris’ Latin Quarter in the days of James Joyce and Ernest…
Santo Domingo
This collection of artisanal food and alcohol vendors is housed under one Zona Colonial roof, with communal courtyard seating. It's a good place to drink…
Kingston
'Wait,' you think as you walk through the door, 'this is just a car showroom.' True enough, but upstairs is a lovely relaxed cafe with good service,…
