"Catch a Boat Ride to Happy Hour Bypassthe roadside watering holes and take a boat ride to Floyd's Pelican Bar, instead. This thatched hut stands on stilts outinthe water, makingit 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 andprevious customershave left messages scrawled on planks and benches. Sit outside and watch the pelicans flying in formation across the horizon."

"Catch the Sunset at Rick's Cafe Rick's is probably the most touristy spot in all of Jamaica, but there's a reason it's listedin 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, thenordera couple of cocktails—Rick's serves up a myriad of options—and stake your claimon a primeviewing 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 whichrise 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 enjoyit almost as much as visitors do."

"Pier 1's greatest appeal is its setting: The open-air restaurant and nightcluboccupiesa 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 runinto the wee hours of the morning. Skip the noisychain restaurant-barsdown 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 ofhis careerwith The Drifters, as well as tales of singing with Eric Clapton andStevie Winwood and Bruce Willis. Sammsopened 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, reggaeis 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 ona breezy porchand out on a fairy-lit patio. Thekitchen serves a Caribbean fusion menu of sandwiches, seafood, pasta, and steaks. In addition to a regular schedule of musical performers, both local and international, Redboneshostspoetry nights, filmscreenings, and art exhibitions."

"In the heart of Barbican, Kingston’s favorite “uptown” neighborhood, Uncorked started as asmallwine and cheese shop but evolved into a sit-downwine bar with a menu that'spopularwith the city’s professional crowd. Pick one of the tapas-style starters like the bacon-stuffed dates, orgo all in and orderone 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."

"Escape in the City Just outside of Montego Bay, in the Ironshore area, you'll find one of the coolest, little-known beachfront bars and restaurants: Memorabilia Bar & Grill. A favorite haunt of some reggae stars as well as locals and expats, it's the perfect daytime escape from the crowds, with an on-site seafood restaurant, serving seafood and burgers, as well as cheap drinks (under US$5 for a rum punch). The kicker: there's a small but gorgeous white sand beach with an eclectic assortment of chairs. You'll feel a world away from the city yet a ten-minute drive away. There's even an over-the-water gazebo where you can sip on your cocktail and take in the blissful Caribbean breeze."