The Best Bars in the Caribbean

By: Maxine Sheppard

January 24, 2011

Whichever Caribbean island you go for, sitting back, soaking up the sun and enjoying a freshly prepared cocktail is the order of the day. From atmospheric, laid-back rum shops and hammock-filled beachfront shacks to intimate lounges and luxury hotel bars, we bring you our pick of some of the best bars the Caribbean has to offer…


Floyd’s Pelican Bar, Treasure Beach, Jamaica


Floyd's Pelican Bar by Alfred Moya on Flickr

Floyd’s Pelican Bar by Alfred Moya on Flickr


Squinting through the sunlight at this seemingly flimsy outpost on a sand bar about a mile off Parrottee Point, you’d be hard pushed to believe it could support a flock of seagulls, let alone a bar and its happy patrons. But Jamaica’s beloved Pelican Bar, made out of driftwood and thatched with palm fronds, stands proudly on its stilts in the Caribbean sea and is a lot more stable than it looks.

After the short boat ride to reach it, treat yourself to an ice-cold beer or jug of rum punch and then laze around for the afternoon. You can swim, snorkel and fish, and if you work up an appetite there’s a great selection of fresh seafood dishes on the menu.


Soggy Dollar Bar, Jost Van Dyke, British Virgin Islands

Tiny, volcanic, and every sailor’s favourite desert island, Jost Van Dyke is only eight square miles in size with just 222 permanent residents. With White Bay, it lays claim to what is consistently voted one of the world’s most beautiful beaches, and the Soggy Dollar Bar at the Sandcastle Hotel only adds to the sheer sense of Caribbean fantasy-come-true.



Soggy Dollar Bar ©

Soggy Dollar Bar ©


This is the birthplace of the legendary Painkiller cocktail (dark rum, cream of coconut, pineapple and orange juice, topped with Grenadian nutmeg) and you’d better watch out because it’s more potent here than anywhere else in the BVI. But if you start to feel a bit woozy, don’t worry. This place is so laid-back they won’t bat an eyelid if you take an extended siesta in one of their palm-shaded hammocks for the rest of the day.


El San Juan Hotel & Casino, Puerto Rico

For those who like to sip their mojitos in the lap of luxury, the El San Juan is the grand dame of Puerto Rico hotels and offers eight different bars to choose from, including the glamorous Gold Bar, a swim-up bar at the oceanfront Encanto Beach Club (where ‘Caribbean mermaids’ serve soy vodka shots at your cabana), and a 360° cocktail experience on the rooftop terrace of the restaurant’s Agave Ranch restaurant.



Gold Bar © Encanto Beach Club, El San Juan Hotel & Casino

Gold Bar © Encanto Beach Club, El San Juan Hotel & Casino


The elegant hotel is located alongside two miles of immaculate beach in the hip Isla Verde district of San Juan and is the place to go for after-dark entertainment, with live music taking place in the lobby and plenty of locals salsa-ing the night away at the Club Brava and Ultra Lounge nightclub.


The Beach House, Barbados

Occupying a great location in the heart of busy Holetown, the upmarket Beach House is probably better known as a restaurant than a bar but its extensive tropical cocktail menu makes it the perfect destination for a sundowner.



The Beach House Barbados

The Beach House Barbados © The Beach House


Try a Rubypolitan or go for one of the house special fresh fruit daquiris, or for those who can’t decide if they’re hungry or thirsty there’s always the famous Beach House Slide –  Vodka, Irish Cream and Kahlua blended with chocolate or vanilla ice cream. Stick around for dinner and you’ll be sure to strike up an interesting conversation or two – this place is equally as popular with Bajans as it is with visitors.


John Moore Bar, Barbados


John Moore Bar ©

John Moore Bar ©


Weston, in the west coast parish of St. James, is home to the John Moore Bar, one of the most characterful hangouts in all Barbados. Essentially an old, brightly painted rum shop with a bar out front – one of literally hundreds on the island – it serves as a social and community hub for its many regulars, with a steady stream of curious travellers passing through. Sit back with a glass of Mount Gay Extra Old and eavesdrop on the local gossip.


Scarlet, Barbados


Scarlet bar ©

Scarlet bar ©


Still in St. James, but with an entirely different vibe, Scarlet is a low-key and contemporary Paynes Bay nightspot, complete with scarlet walls (of course) and adorned with prints of Marilyn Monroe and Jackie O.

A hip and trendy alternative to the more beachy establishments, this is the lounge to head to for a têteà-tête over a late-night martini.


Opus Bar, Havana, Cuba

Located above the Teatro Amadeo Roldán in the Vedado district of Havana, on the corner of Calle D and Calzada, Opus is the closest thing the city has to an old-school Vegas-style lounge bar. There are fabulous views from its huge windows, a retro ’50s-style interior with fat, comfy sofas, and a second-to-none cocktail menu. Atmospheric and unpretentious, and a little way from the main tourist strip of bars means you’ll feel like it’s your own personal discovery.



Bar Monserrate, Havana, Cuba

A block up from Hemingway’s old hangout the Floridita, the Monserrate is an old, nostalgic wood-panelled bar where the waiters wear smart black waistcoats, faded photographs hang on the walls and the wide ceiling fans quietly drone above.


The cocktails here are excellent value for this popular part of Old Havana, but best of all is the music. You’ll almost certainly be treated to a performance by one of Havana’s traditional Son or Salsa bands, and don’t let anything stop you taking to the floor if the moment takes you. Check out this video below by travel writer David Lansing for a taste of what you can expect.



Bar Monserrate in Havana, Cuba from David Lansing on Vimeo.

For those who are equally as passionate about the food of the Caribbean as they are its cocktails, check out our recent post on where you can learn to cook, as well our suggestions for the best tunes for watching the sunset.

Thanks to Alfred Moya on Flickr for the photo of Jamaica’s Pelican Bar.

Virgin Atlantic fly to a wide range of Caribbean destinations from London Gatwick airport. For full details and the very best fares, log on to or visit Virgin Holidays for a tailor-made trip.


Maxine Sheppard

Maxine is the co-editor of the Virgin Atlantic blog. Travel and music are her joint first loves, and despite having written for Virgin for more years than she cares to remember she still loves nothing more than jumping on a plane in search of new sights and new sounds.

Categories: Our Places