The Best Bars in Jamaica

Bypass the roadside watering holes and take a boat ride to Floyd’s Pelican Bar, instead. This thatched hut stands on stilts out in the water, making it a dreamy spot for an afternoon of swimming and shooting the breeze, solo or with friends. It’s 30 minutes from Treasure Beach (arrange a boat ride through your guesthouse or resort), and you can arrive for lunch and stay until after sundown for the just-caught fish, rum, and chilled Red Stripe on the menu. Inside the tiny shack, the flags of various countries hang and previous customers have left messages scrawled on planks and benches. Sit outside and watch the pelicans flying in formation across the horizon.

Rick’s is probably the most touristy spot in all of Jamaica, but there’s a reason it’s listed in 1,000 Places to See Before You Die, so don’t miss experiencing it at least once. Get there around 4 p.m. to avoid the crush of tour bus traffic that happens closer to sunset, then order a couple of cocktails—Rick’s serves up a myriad of options—and stake your claim on a prime viewing spot for the sunset and cliff-diving. Local divers swing from trees and drop into the surf or plummet from the surrounding cliffs, some of which rise more than 30 feet above the sea. Even the occasional tourist will brave the jump into the water below. A reggae band adds to the animated vibe. Lest you feel like just another tourist sheep at the sunset very-happy hour, console yourself in knowing that locals enjoy it almost as much as visitors do.

Pier 1’s greatest appeal is its setting: The open-air restaurant and nightclub occupies a pier that extends out into the Caribbean in Montego Bay. By day and into the early evening, the restaurant draws visitors and locals interested in a good meal with a stellar water view. At night, regular parties start late and run into the wee hours of the morning. Skip the noisy chain restaurant-bars down the street and try something more Jamaican, instead.

Remember the oldie “Under the Boardwalk” by The Drifters? The owner of Drifters Bar, Luddy Samms, tells stories of his career with The Drifters, as well as tales of singing with Eric Clapton and Stevie Winwood and Bruce Willis. Samms opened this hot-spot bar and performance venue on Seven Mile Beach in 2011, and expats, locals, and tourists flock here for cold Red Stripe, good food, and lots of live music in a variety of genres. Because this is an authentic Jamaican beach bar, though, reggae is king.

Start your night out in the trendy New Kingston neighborhood with dinner at Redbones. The warm wood interior is hung with photos of jazz and blues artists who have performed here. Several seating areas inside and out can suit a variety of moods. Tables are set on a breezy porch and out on a fairy-lit patio. The kitchen serves a Caribbean fusion menu of sandwiches, seafood, pasta, and steaks. In addition to a regular schedule of musical performers, both local and international, Redbones hosts poetry nights, film screenings, and art exhibitions.

In the heart of Barbican, Kingston’s favorite “uptown” neighborhood, Uncorked started as a small wine and cheese shop but evolved into a sit-down wine bar with a menu that’s popular with the city’s professional crowd. Pick one of the tapas-style starters like the bacon-stuffed dates, or go all in and order one of the famous-for-good-reason gourmet burgers—including the Scotchie and Skellie, which is spiced Jamaican-style. The salads, seafood, and meat entrées don’t disappoint, either. All meals can be paired with the huge selection of imported wines, including vintages from Europe, Australia, and South Africa. It gets crowded at lunchtime, and tables are few, so come early to avoid a wait or stop in for evening cocktails and cheese and olive platters.