The souvenir t-shirt hanging on the wall of the bar says it all: Happy Hour is the reason I get up in the afternoon. Forget “One Happy Island,” or “Out of Many, One People” -this nod to cold beer and frozen concoctions is the unofficial motto while vacationing in the Caribbean. At the same time, after drinking a couple rum runners, whatever cay or islet you’re visiting will indeed feel like one happy island.
There are over 7,000 islands in the Caribbean’s 1,063,000 sq. miles of sparkling blue sea, and while many are half-submerged or uninhabitable -treasure islands inaccessible to even the wealthiest and most connected traveler- there are plenty of places to grab a cold drink when vacationing in the Carribbean. Squinting behind Ray-Bans, you’ll see palm-thatched Barbadian rum shacks and 5-star resort swim-up bars. Hotel bars, pool bars, cigar bars, piano bars, atmospheric lounges, laid-back, wood-panelled hideaways that evoke 1950s Hollywood glamour -the Caribbean has a little of everything, however quirky and eclectic.
What makes one Caribbean bar stand apart from the next? What’s the criteria for making a bar an elite drinking establishment? It’s a simple recipe: 1 oz. attitude, 1 oz. latitude, a splash of sunshine, a hint of romance, put it all in a blender, crush, pulse and voila…you have a bar that can only be described as irie. So, whether you’re ordering a Painkiller or a Pina Colada, let the bar hopping begin.
10 The Dune Preserve -Anguilla
Tucked away in Rendezvous Bay, The Dune Preserve is a sprawling, ramshackle beach bar made out driftwood, seashells, and materials salvaged from shipwrecks. What gives The Dune Preserve elite status? CNN voted it the #1 beach bar in the world. More importantly, Kevin Bacon comes to The Dune Preserve to play music when he’s in Anguilla. The funky beach hideaway is owned by reggae star Bankie Banx.
Aruba, Bonaire and Curacao are the western-most islands in the Leeward Antilles and located just north of Venezuela. The ABC islands have so many breathtaking, beachfront bars that choosing just one from the Dutch chain seems as hidden as venturing to the Caribbean and then hiding indoors for the time on vacation.
9 The Moomba Beach Bar -Aruba
The Moomba Beach Bar, in Aruba, is a classic tropical island-style Tiki bar. The bar is steps away from the ocean and features palapas shade huts and lounge chairs. Moomba specializes in simple, grilled seafood, and there is live music day and night.
There are hundreds of bars like Moomba in the Caribbean, but not all of them do simplicity right; Moomba excels at it.
8 La Balandra Beach Bar -Bonaire
Designed to look and feel like an antique Spanish ship, Bonaire’s La Balandra Beach Bar and Grill is constructed on a jetty extending into the sea. Stand at the bow and you’ll have the feeling the La Balandra is slowly cutting its way through the shallow turquoise waves.
The views of the bay are spectacular, and if you happen to have one too many, no worries, just blame it on a lack of sea legs.
7 Avila Beach Bar and Restaurant -Curacao
In 2013, The Caribbean Journal included Avila’s Blues Bar and Restaurant in its list of “The Caribbean’s Top Ten Hotel Bars.” The Curacao institution has been a hotspot for over 20 years, serving up blues and Latin jazz as well as a host of popular theme nights. The combination of award-winning food, live music and location –Avila bar is located on a pier –making it an elite Caribbean watering hole.
6 The Soggy Dollar –Jost Van Dyke, British Virgin Islands
The term elite doesn’t necessarily have to mean expensive or exclusive; it can also mean influential. And there’s no bar in the Caribbean more influential than The Soggy Dollar, which is located on White Beach on Jost Van Dyke, the smallest of the four British Virgin Islands. Legend has it “The Painkiller,” one of the Caribbean’s signature drinks (recipe: rum, cream of coconut, orange and pineapple juice, a dash of nutmeg) originated at The Soggy Dollar in the 1970s. But that’s not the bar’s only claim to fame. Until recently, the only way thirsty customers could reach the bar was to swim from their anchorages. Dollars got soggy and had to be clipped on a line at the bar to dry. Nowadays, The Soggy Dollar Bar is accessible by road, and because of its legendary status, it no doubt accepts all major credit cards, too.
5 The Monkey Bar -Sandy Lane Resort, Barbados
Sandy Lane has been the Caribbean’s premier address since 1961, when it first opened its doors to guests. The idyllic resort looks like a summer retreat out of F. Scott Fitzgerald’s “The Great Gatsby.” All of Sandy Lane’s seven bars are perfect for limin with a Mount Gay Extra Gold Rum or glass of cognac. However, The Monkey Bar, on the hotel's lower level, stands out; the bar is not only cozy and classy, but the themed murals and unusual artifacts make it feel as if you’ve stumbled into an archeologist’s private study. After a couple of drinks, your inner adventurer will shine like the sun over Bridgetown. A luxury room at Sandy Lane costs between $1,490-$2,380. Tiger Woods reportedly spent 1.5 million when he married Elin Nordegren at the luxury golf and spa resort in 2004.
4 Piano Bar -Couples Tower Isle Resort, Jamaica
Jamaica is one of the original playgrounds of the rich and famous. American fashion designer Ralph Lauren has a plantation-style beach house near Montego Bay that he purchased over 20 years ago, and Ian Fleming, the creator of James Bond, had an estate named Goldeneye on the island’s northern coast, where he wrote all 14 of the Bond books.
Couples Tower Isle Resort (formerly known as Couples Ocho Rios) was a private island getaway that catered to the Hollywood jet set in the 1950s and 60s. If you thought Anita Ekberg’s dip in the Trevi Fountain represented "La Dulce Vita," her midnight swim is nothing in comparison to the boozing and carousing that took place at this Hollywood hangout. Today, the Couples Resort’s vintage Piano Bar aims to evoke the glamorous spirit of that age. Photos of the resort’s famous guests dot the walls, and after knocking back a couple of the mixologist’s cocktails, you may even think Frank Sinatra or Truman Capote is sitting at the bar with you.
3 The Gold Bar -El San Juan Hotel and Casino, Puerto Rico
The El San Juan, the Grand Dame of Puerto Rican luxury hotels, emanates Old World style and sophistication. Located in the Isla Verde district of San Juan, the hotel is a high-roller’s paradise. There’s not one, or two, but eight different bars to choose from, all of which are perfect examples of blue-ribbon elegance. The famous Gold Bar (the name says it all, right?) pulses with Las Vegas intensity, while the hotel’s rooftop terrace allows you to enjoy a mojito 360-ways to Sunday. Outside, the oceanfront Encanto Beach Club has one of the sleekest swim-up bars in the Caribbean.
2 Nikki Beach -St Barth
Nikki Beach is a like a second home to celebrities, a VIP hotspot to soak up the sun and see and be seen. Celebrity guests at the oceanfront bar and beach club have included Jay Z, Beyonce, Fergie, Ashton Kutcher, Demi Moore, Mariah Carey, and Bono, among others. The uber-contemporary hangout is known for its lavish fashion shows, live performances, and themed events.
At night, resident DJ Jacques Dumas spins house music as affluent tourists pass the Courvoisier to movie stars, supermodels, and royalty. Nikki Beach is a trendsetting locale, and it was called “The Sexiest Place on Earth” by The London Observer.
1 Yara Bar – Amanyara Resort Hotel, Turks and Caicos
When it comes to the good life and jaw-droppingly beautiful islands, the Turks and Caicos set the gold standard. If Michelin stars were awarded to islands instead of restaurants, this British territory would lead the way. The Amanyara Resort Hotel (the name means “peaceful place” in Sanskrit) has received accolades from Conde Naste Traveler, Gallivanter’s Guide, and U.S. News and World, and there’s no more peaceful place at the resort than the Yara Bar. The bar is circular in design with a soaring, airy ceiling –perfect for afternoon trade winds- and features a number of oversized lounging daybeds around its perimeter. Leading from the bar is a spacious terrace and swimming pool. Sweeping views of the ocean form an ideal backdrop for an afternoon Pimm’s cup or a post-dinner cigar. Prices at the Amanyara Resort Hotel range from $1,350-$9,900 a night, depending on whether you want a pavilion or a 5-bedroom beach villa.
Whether you’re looking for the Southern Cross, “nibblin’ on sponge cake, watchin’ the sun bake,” or waiting for the green flash to light up the horizon when the sun sets, pull up a stool and enjoy the view from one of these treasured Caribbean bars.