If there’s one thing the Caribbean has plenty of, it’s beaches. And when you consider that every beach has a multitude of enticing bars all clamoring for your attention, choosing the best one can become a nearly impossible task. Everyone you meet will wax on about their favorite drinking spot, but there are a few standouts that demand a secure place on every Caribbean traveler’s to-do list. These five are legendary. Bottoms up!
Sunset Bar & Grill, St. Maarten
Be prepared for a trippy time at one of the Caribbean’s most unusual watering holes. Maho Beach has a serious party-hearty atmosphere, especially during the week thanks to the cruise ship crowd. But the biggest thrill is encountering a jumbo jet flying just feet above your head. That’s because Sunset Bar is positioned at the end of Princess Juliana International Airport’s runway. Aviation geeks tune in to air traffic control conversations via the bar’s speakers and then get out their binoculars. Others prefer dancing, betting on racing crabs (really), or downing $2 vodka-and-fruit juice “take-off” shots. Warning: this bar has a “topless ladies drink free” policy, so keep that in mind, either for your budget or your blush factor.
The Bar on Sandy Island, Anguilla
To get to this tiny private island off Anguilla (it's been featured on The Bachelor, of course), take the 10-minute sea shuttle ($10 roundtrip) or hop in a dinghy and motor yourself there. Once you arrive, you’ll find a single, open-air pavilion and an assortment of colorful picnic tables. Have a seat and feast on grilled spiny lobster, crayfish, and ribs while sipping a rum punch – or three, since there are twelve varieties of the liquor on hand. Bring a bit of cash, as the Gilligan’s Island-like atmosphere isn’t cheap, nor is personal picnicking allowed. Still, it makes for a great day trip, so kick back on a beach chair and catch some rays. Or, grab your snorkel gear and get a closer look at the creatures of the turquoise reef.
Moomba Beach Bar, Aruba
This club-like space in Aruba’s popular Palm Beach area is known for its rollicking party vibe. At the busy bar, you can order from a varied list of cocktails and the local Balashi beer, which is discounted during the daily sunset happy hour. Dancing is highly encouraged by the enthusiastic DJs and live bands who play everything from reggae to pop music on a daily basis. If you get hungry there’s a full restaurant menu, but the most exciting item on it is the traditional Aruban fish chowder soup. Otherwise, keep on sipping and swimming.
Da Conch Shack, Providenciales, Turks and Caicos
True to its name, this white-clapboard house isn’t much to look at. But decor isn’t the draw here: tourists come in droves for a taste of the freshly-cracked conch dishes on offer. While you’re waiting for your conch salad or fritters (it takes a while; you’re on Caribbean time), you can pass the minutes nursing a cup (or pitcher) of the strongest rum punch available on the island.
Once you make it all the way to remote Nevis in the West Indies’ Leeward Islands, you’ll be parched from the journey. Nearly everyone, tourist or not, will point you to Sunshine’s, an easy-breezy bar decorated in the Nevis’ national colors of red, green, and black, and decorated with license plates from returning patrons. What should you order? The signature drink, The Killer Bee, is a steal at $5. Don’t bother asking what’s in it. Sunshine himself, who’s often on property, will only say rum and passionfruit juice. But trust us, there’s much more going on here than meets the eye. Drink responsibly, and keep your belly full of barbecued wings, and you may just avoid ending up on the stage during karaoke hour.