Vieques
Locals, expats and visitors head to this oceanfront dive bar to mingle long past the sunset happy hour. Weekends mean live music, open jam sessions and…
Must-see nightlife in Caribbean
Montego Bay
Trapped on Doctor’s Cave Beach (you pay to enter), your only drinking and eating option is the Sand Bar. The food – burgers, seafood and such – is…
Tobago
In the center of Pleasant Prospect, this is a good place to hang out with folks. It has a surfer vibe and friendly clientele, and there are pool tables…
Kingston, Blue Mountains & the Southeast Coast
This is a funky watering hole drawing locals who wash in and out and overindulge in white rum. It has tremendous character on Friday night when a mountain…
Bermuda
DJ sets at the 'Cosmo' cater to a crowd in their 20s and 30s that likes to rock out to hits from the '80s and '90s and whatever's hot on the radio. Themed…
Tortola
Boaters drift into Rhymer's, a Cane Garden Bay stalwart, for breakfast and midday beers. Crowds die out by afternoon, when the neighboring bars start…
Culebra
Head to this lively waterside joint for the drinks rather than the food – mainly seafood and pasta. Try the Bushwacker, the island's potent signature…
Vedado
An insanely popular nightclub, Pico Blanco is on the 14th floor of the mediocre Hotel St John's. The program can be hit or miss. Some nights it's karaoke…
Culebra
A hot spot for locals and expats, this sports bar has a vast outdoor deck opening onto the bay – perfect on warm nights – and an indoor lounge with a pool…
Cabarete
Vela Windsurf Center by day, bar by night, this small, hip cafe also serves sandwiches and snacks. Monday karaoke is a mandatory part of Cabarete beach…
Port of Spain
Once at the forefront of the Port of Spain nightlife scene, 51 is a bit past its prime, but it's still a good spot for some clubbing vibes. Thursday is…
Tortola
The Elm is the smallest and perhaps the most welcoming of all the beachfront joints on Cane Garden Bay, great for kicking back with a beer and chatting…
Aruba
Aruba's locally brewed beer isn't anything to rave about, but it's still neat to learn how this light pilsner is made locally from imported Scottish malt…
Cienfuegos
Liquid lunches were invented with El Palatino in mind – a dark-wood bar set in one of the city's oldest buildings on the southern side of Parque José…
Tobago
Overlooking the ocean, with its outdoor deck cooled by sea breezes, this popular bar and nightspot has pool tables and regular special events that draw a…
Habana del Este
With its luminous interior and open terrace overlooking the street, the Luna is all restaurant but is more popular for its drinks and nighttime action…
Barbados
This colorful wooden bar is poised right on the grassy foreshore by Mushroom Rock, but unfortunately the deck faces the wrong way – to the road rather…
Cabarete
A beachside sports bar with NFL, NHL, NBA and games from many other league acronyms on the big screen, along with regular food and drink specials. Late…
San Juan
This self-proclaimed gay 'minibar' – 'get out if you can' in local parlance – features nightly acts with drag queens, singers, strippers and poets. Shows…
Santiago de Cuba
Enlivening Paseo Alameda with its lively ranchón-style bar suspended over the water with a great view over the bay, this is a breezy locale to escape the…
Santo Domingo
An Italian cafe popular with tourists and worth noting for its location occupying a prime piece of cobblestone real estate, good for an espresso drink or…
Holguín Province
Right on the sand at Guardalavaca's liveliest strip of beach, Pirata is your standard beach shack with beer, music and enough ingredients to muster up a…
Barbados
A spacious indoor/outdoor club with split levels that doesn't feel too claustrophobic. There's plenty of space to sit – you might even manage a…
Guantánamo Province
This shell of a ruined colonial building has 9m ceilings, and there are plenty of benches to prop you up after you've downed your nth beer. There's a…
Artemisa & Mayabeque Provinces
An attractive garden club that puts on occasional comedy shows organized in conjunction with the Museo del Humor. The clientele is a mix of townies, folk…
Holguín
Sells drinks and snacks (CUC$1 to CUC$4) beneath flowering trellises on Parque Calixto García, and it's a relaxed place to meet other travelers. If you…
Bayamo
Ice-cold air-con, starched tablecloths, stern waiters, good live music from piano recitals to trovadores (folk singers) and crooners of musica romantica…
Holguín Province
Another quiver in Gibara's freshly renovated bow, this bar next to the Casa de la Cultura hosts live music on Friday and Sunday nights, but is always a…
Kingston
Popular New Kingston sports bar that's good for inexpensive drinks (and free drinks promotions), decent food off the grill, followed by a loud music mix…
Isla de la Juventud
Extremely loud music and most of the town's teenagers and 20-somethings converge by the historic boat for alfresco dancing. Drink and snack stalls also…
Havana
A romantically disheveled place on the Malecón that's named after Chilean man of letters Pablo Neruda, this cafe is better for its drinks than its food…
Port Antonio
This is Port Antonio’s infamous hang-loose, reggae and dancehall bar, where the tunes are loud and you’re fair game for any stranger who wants to try to…
Vedado
This small, darkly lit piano bar attracts something of an older Cuban crowd with its regular diet of boleros (ballads) and trova (traditional music),…
Carriacou
Pretty much the only place on Tyrell Bay to get a decent coffee in the morning, the Gallery Cafe also serves full English breakfasts and light meals. Get…
Grande-Terre
This bright, lively cafe near the ferry port serves cocktails, rum and just about any other beverage you might name to a bouncing Caribbean soundtrack. It…
Cienfuegos
It's difficult to say what the Barbarian of Rhythm, Benny Moré, would have made of this disco-club named in his honor. Bring your dancing shoes, stock up…
Holguín
A grotty tavern on pedestrian-only Manduley, where wooden tables and ceramic mugs create a hearty olden days atmosphere. Solo travelers elicit more than…
Tobago
Leggers is an unpretentious bar nooked into a cliff overlooking the ocean. It catches lovely breezes and is a great spot to snag a beer after a day of…
Tobago
Happening bar with a dance floor, offering chilly cocktails and beers, and the biggest party crowd in Crown Point. Often puts on special events: karaoke…
Isla de la Juventud & Cayo Largo del Sur
Taberna el Pirata is primarily a haunt for boat hands, resort workers and the odd escaped tourist alongside Marina Internacional Cayo Largo. Icy beer,…
