The Best Bars in the Cayman Islands

Grand Cayman, known for its sprawling Seven Mile Beach and world-class scuba diving, has its first new resort in more than a decade. Most of the 266 rooms at the Seafire offer views showcasing the sunsets that inspired the property’s name. The three restaurants include the seasonal, small-plate Ave, whose 24-seat chef’s counter, Avecita, serves a Spanish tapas tasting menu. At the bar off the lobby, try a cocktail featuring tepache, a beverage made from fermented pineapple rinds.

Though it lacks a beach, this family-owned and professional diver–managed resort on the rocky coast just south of George Town has direct ladder access into the Caribbean. Grand Cayman’s two famous underwater sites, Eden’s Rock and Devil’s Grotto, are just a short swim away, and boat trips offer the option of two daily dives (including night dives). Images by some of the world’s most respected underwater photographers decorate many of the tiled and comfortable smoke-free rooms, some of which have kitchens and private balconies or terraces. The vibe is laid-back; post dive, guests sit by the pool or swap stories at the palapa bar, which has the island’s best sunset vista. Managers Anne Briggs and Lisa Evans, the granddaughters of Sunset House’s founders, make sure everything runs smoothly and ensure visitors explore the best of Grand Cayman both on shore and underwater.

This honky-tonk-inspired bar has a hometown feel and a country vibe, and has great local beers on tap—like Grand Cayman’s classic premium lagers, the CayBrew and Caylight. Don’t miss out on the Thursday night Rock & Roll Bingo: It can get rowdy and is a lot of fun. Lone Star Bar and Grill is well known for its BBQ, including Texas-style ribs as well as barbecue chicken and burgers. When you get the munchies after a few beers it’s a nice break from the gamut of seafood offered at other establishments.

Giving new life to an old haunt, the Cayman Spirits Company has turned the onetime bar area of the historic Pedro St. James into a rum-centric saloon and café: the Outpost Bar. Go for a tasting, and you’ll try as many as five local rums, one of which—the 1780—is aged and available exclusively on-site. The next most important variety to sample here is the Seven Fathoms, if only so you can say you’ve tasted rum that’s been anchored and aged 42 feet (i.e., seven fathoms) below the Caribbean’s surface. Of course, considering the Outpost’s view—prime, uninterrupted seascape—you could have pretty much any drink in hand and be happy.

Among vacationers who’ve been coming to Grand Cayman forever, there’s a whole faction that essentially camps out at Rum Point all day every day, and you’ll understand why as soon as you see the place. Tucked away, super low-key, and graced with a ridiculously photogenic pier—its perfectly weathered planks cutting a striking figure against the tranquil, turquoise surroundings—this beach is the ultimate spot for settling into a lounger or hammock between water-sports outings. Rum Point’s namesake booze—which used to wash ashore by the barrel, according to legend—is available in all manner of cocktails here, of course. But order at least one mudslide at its spiritual birthplace: the beach’s beloved Wreck Bar.