Santiago de Cuba
You know Cuba is changing when you find an actual warehouse-style brewpub filled with locals quaffing pints brewed on-site. The four beers at this noisy,…
Must-see nightlife in Caribbean
Ocho Rios
With its prime spot on the pier, it’s little surprise that Ocean's 11 is popular with cruise-ship passengers, who knock back cocktails by the bucket…
Habana Vieja
An offshoot of the hip Miramar bar, Espacios inhabits a smaller abode in Habana Vieja but, like its bigger sibling, adorns its walls with eye-widening…
St Vincent & the Grenadines
Fabulously chic for grubby downtown Kingstown, Flow is a dimly lit top-floor bar with sofas to spare, a chilled soundtrack and an extensive selection of…
Port-au-Prince & Around
The rooftop lounge at Karibe Hôtel is unquestionably Pétionville's most fabulous venue to throw back a few cocktails and snap a selfie for the 'gram –…
US Virgin Islands
This low-lit beer house with exposed stone walls and a horseshoe-shaped mahogany bar is almost like a speakeasy on the back end of the Billabong store…
Saba
Part of Tropics Cafe, this lively bar is a fun post-dive or hike hangout. Happy hour (4pm to 6pm) brings two-for-one beers and is best on Fridays. On…
Varadero
In recent years, Varadero has sprouted a copy of Hemingway's favorite Havana dive bar, aka La Bodeguita del Medio, a cool place where musicians strum in…
Punta Cana & the Southeast
A favourite of local expats who thought tourists would never find it. Think again! Tucked away in a residential neighborhood less than five minutes' walk…
St John
This minimum-footprint pop-up village has a beach shop, a food truck, water sports, cornhole (a lawn game) and colorful picnic chairs, all set amid a…
Barbados
This spacious bar is popular with both locals and visitors and plays a somewhat frustrating mix of good dancehall and bad pop. There's an air-con dance…
Barbados
Hang out with a bunch of charming old gents at Mr Bradshaw's no-nonsense waterside bar in the small village of Six Men Bay. It's little more than a zinc…
Bávaro & Punta Cana
If you'd like to avoid gaggles of tourists, head straight to Drink Point at the corner of Av España and Av Francia, where Dominicans pack in nightly. The…
Varadero
In the Miami-esque Marina Gaviota at the eastern end of the peninsula, you get a Miami-esque cafe. The Isabelica tries to impress Starbucks-starved…
Santo Domingo
Dozens of imported craft beers from around the world, including a good representation of Belgian and German ones served up – slowly, when busy – on the…
Anguilla
The beer is ice-cold, the margaritas are strong and the rum punch is laced with amaretto at Elvis' salty beach bar, which also has a feisty menu of…
Jimmy Buffett’s Margaritaville
Negril
The home of the 'cheeseburger in paradise,' Jimmy Buffett’s sustains a spring-break vibe all year long, although it has a bit of a forlorn air on slow…
St Vincent & the Grenadines
Located right on the sands within the boundaries of the high-end Sandy Lane Yacht Club, Shenanigans is the place to go to rub shoulders with ultra wealthy…
St-Barthélemy
A resident DJ and international guests spin a mix of EDM, reggae, funk and other danceable sounds until the wee hours beneath vaulted dark timber-beamed…
Kukara Macara Country Bar & Restaurant
Santiago
Customers enter through old saloon doors and are welcomed by servers dressed like cowgirls and cowboys at this kitschy but fun western-themed restaurant …
British Virgin Islands
The original Willy T's was destroyed in Hurricane Irma. Version 2.0 of this floating bar is bigger and cleaner, though just as rowdy. Conch fritters and…
Habana Vieja
Worth incorporating into a neighborhood bar crawl, even if the 'pub' moniker is a bit misleading (the only beer it has is bottled Heineken). The eclectic…
St Kitts & Nevis
This nattily designed beach bar right on tranquil White House Bay is about as cool as things get in St Kitts (check out that distressed corrugated iron)…
US Virgin Islands
This beyond-the-norm sports bar lets you sip a decent beer selection and cheap bourbon drinks while munching juicy burgers and thick, hand-cut fries in…
St-Barthélemy
Moulin Rouge meets Cirque du Soleil in this supper-club cabaret where the chic and inhibition-free frolic in a sensuous fantasy setting. Reservations are…
Grenada Island
This is lovely little spot at the end of Mourne Rouge beach is a great place for a drink. It consists of a shaded deck with colorful wooden furniture and…
Bermuda
There are three things to like about the Dock at the Waterlot Inn: the comfy banquettes in a terrific waterfront location, ideal for sunset-watching; the…
Louis & Steen's New Orleans Coffee House
Nassau
If you're after good coffee, head to this colourful cafe about 16km west of downtown, where single-origin beans are roasted, brewed and served as espresso…
Las Terrenas
Canadian-owned One Love is a great place to down a few cold ones (there's a two-for-one happy hour from 5pm till 8pm) to the tune of crashing waves – you…
Habana Vieja
This once-seedy, now polished bar by the docks broadcasts a list of former rum-slugging patrons on a plaque by the door: Federico García Lorca, Marlon…
Bermuda
It's hard to pin down the Pickled Onion. There's the somewhat pub-like ambience (only with funky contemporary art), but the drinks lean towards a solid…
Habana Vieja
Founded in 1772 and glowing after a 21st-century makeover, this drinking and eating establishment is a favorite of cruisers and tour groups, who prop up…
St-Barthélemy
Completely rebuilt after Hurricane Irma, this vaunted beach club is back with a vengeance as well as an outdoor dining area, a sushi bar and a rotisserie…
Negril
The only bona fide nightclub outside the all-inclusives, Jungle, with its tacky decor, is not the most urbane place, but the DJs definitely know what they…
Bermuda
One of Hamilton's most popular after-work drink venues. The shady patio next to the decades-old Italian restaurant is handy for people-watching and…
Montego Bay
Proper is often packed with locals and expats returned to the motherland. It’s a friendly, occasionally raucous spot and probably the easiest bar for…
Jimmy Buffett’s Margaritaville
Montego Bay
Of the three Margaritavilles in Jamaica, this one is a tourist trap by day, but as night falls, locals like to come here to dance to pounding beats loud…
Santo Domingo
A diverse mix of capitaleños (Santo Domingo residents) get down to son (Afro-Cuban percussion), bachata (popular guitar music based on bolero rhythms) and…
Port of Spain
A great place to party, with a young and beautiful crowd dancing the night away, sipping cocktails and nibbling on Peruvian food from the in-house…
US Virgin Islands
Cavernous, open-air Greenhouse overlooks the harbor and rocks hard during happy hour (4:30pm to 7pm, when drinks are two for the price of one). The…
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