16 Best Nightlife in Cayman Islands

This classic beach bar has a huge deck over the water, thatched roof, amazing mosaic murals of waves, spectacular sunsets (and sunset-color libations), and tiki torches illuminating the reef fish come evening. Macabuca means "What does it matter?" in the Indigenous Antillean Taíno language, perfectly encapsulating the mellow vibe. Big-screen TVs, live bands and DJs on weekends, excellent pub grub, and daily specials (C$9 jerk dishes on weekends; Monday all-night happy hour, DJ, and C$17 all-you-can-eat barbecue) lure everyone from well-heeled loafers to barefoot bodysurfers animatedly discussing current events.

This delightful seaside slice of old Cayman—grizzled regulars slamming down dominoes, fabulous sea views, old model cars, Friday-night dances to local legend Lammie, karaoke Saturday with Elvis impersonator Errol Dunbar, and reasonably priced red conch chowder and jerk chicken sausage—is also a big politico hangout. Fascinating photos, some historical, show local scenes and personalities. The juke jives, from Creedence Clearwater Revival to Mighty Sparrow.

It's easy to overlook this bar at the entrance to the Kimpton Seafire's main restaurant unless you're waiting for your table, but that would be a mistake. It's not the decor, which is surprisingly sterile despite the handsome driftwood sculpture hanging from the cathedral ceiling. Rather it's the gregarious mixologists who hold court, inventing cocktails on the spot based on your personality and preferences. You can also order dinner from the extensive regular Ave menu, including such standouts as crispy octopus with warm potato-and-white-bean salad or cavatelli with rabbit ragù.

If you blink, you might miss this intimate speakeasy off West Bay Road. However, it offers an air of sophistication reminiscent of the Prohibition years. Famous for award-winning craft cocktails and a vast selection of spirits, it's a place to relax in a leather chair. Smokers can peruse the vast cigar humidor offering a diverse selection to suit even the most discerning cigar aficionado.

New Yorker Terry Chesnard built his dream bar from scratch, endowing it with an almost 1960s Rat Pack ambience. Nearly everything is handcrafted, from the elegant bar itself to the blown-glass light fixtures to the drinks. Try the Barracuda shot special "if you dare," or the cocktails, though Terry takes the greatest pride in his top-of-the-line espresso machine. The kitchen elevates pub grub to an art form with pizzas, Reubens, and French melts. Locals flock here for free-pasta Friday, karaoke Wednesday, and live music on Thursday. You might walk in on a hotly contested darts, shuffleboard, or dominoes tournament, but the vibe is otherwise mellow at this charming time-warp hangout.

The popular restaurant and bar, adorned with wild murals, fab old-timer photos, and surfboards doubling as signs, offers a classic Cayman sight: fishers anchor their boats right offshore and display their catch right outside (condo and villa renters, head here if you're in the market for fresh fish). The capable kitchen specializes in classic Caymanian cuisine; farm-to-table Thursdays are justifiably popular. This is also a prime pyrotechnic sunset- and cruise-ship-watching spot, where locals laze in locally carved chairs, sipping house microbrews on the vast thatch-shaded, tiered deck. Stop by the Swanky Shack by the entrance for souvenir T-shirts and island gossip.

You can sit at the bar or swing under a century-old poinciana tree and watch the traffic go by. There are murals of apes everywhere, from gorillas doing shots to a baboon in basketball uniform (in keeping with management's facetious suggestion that you attract your server's attention by pounding your chest while screeching and scratching yourself). Friday swings with DJs and free happy hour munchies. Popular for breakfast.

Known islandwide as Bussy's after the larger-than-life owner, La Esperanza overflows with drinks and good cheer. On weekends, seemingly half the island can be found here, when Bussy fires up the grill and hosts a huge beach jerk barbecue (he'll occasionally give impromptu jerk lessons). Shoot pool in the colorful lounge, or pass time at the alfresco bar or the covered pier jutting into the Caribbean. Drink in the sunset views (and cocktails in matching colors), and if available, try the luscious Key lime pie made by Bussy's wife, Velma. The music, heavy on the reggae with the occasional salsa tune thrown in, blares, encouraging everyone to sway along.

This sports bar has a clubby, retro feel—Marilyn Monroe and Frank Sinatra photos channel glamour days, while scarlet booths and bubble chandeliers add oomph. Good luck wrestling a spot at the bar for pay-per-view and major sporting events, but 10 TVs, including two 6-by-8-foot screens, broadcast to every corner. Also an entertainment venue, Legendz books local bands, stand-up comics, and island DJs, and serves grilled fare at reasonable prices.

Perched on the water's edge, this bar has great sunset views. The leviathan open-sided cabana is drenched in Rasta colors and crowned by an intricate South Seas–style thatched roof with about 36,000 palm fronds. Christmas lights and the occasional customer dangle from the rafters. It offers great grub, and the crowd is a mischievous mix of locals, expats, and tourists.

Both fishermen and financiers savor sensational sunsets and joyous happy hours, then watch tarpon feeding at this open-air, marine-theme bar on a jetty. Boaters and snorkelers, before and after checking out the wreck of the Cali, cruise up the ladder for drinks, while anglers leave their catch on ice. There are complimentary snacks on Friday and pub fare at fair prices until midnight.

This chic sports bar has three billiards tables, classic arcade games (Space Invaders, Donkey Kong), air hockey, and large-screen TVs (nab a private booth with its own flat-panel job). Events are daily happy hours, trivia nights, and the Caribbean's reputedly largest Bloody Mary bar on Sunday. Along with sister "O" Bar, it's ground zero for the Wednesday Night Drinking Club. For a C$25 initiation (with T-shirt and personalized leather wristband, toga optional) and C$10 weekly activity fee, you're shuttled by bus to three different bars, with free shots and drink specials.

This spot draws an eclectic group of dive masters, expats, honeymooners, and mingling singles. The knockout, colorful cocktails pack quite a punch, making the sunset last for hours. The bar dialogue is entertainment enough, but don't miss local legend, country-calypsonian Barefoot Man, when he plays "upstairs" at Tides—he's to Cayman what Jimmy Buffett is to Key West.

This is indeed a preferred hangout for the diverse after-work crowd, which packs both the cozy club space (adorned with customers' ties) and breezy patio, absorbing the high-octane cocktails and nightly musical mix (from country to salsa and karaoke to live bands). Happy hours are joyous indeed with C$5 martini specials. It's invariably lively—a favorite spot for birthday, office, and bachelor and bachelorette parties and a prime place to eavesdrop on local gossip.

Dance near the water to mellow music on Saturday evening; when there's a wedding reception in the pavilion, the crashing surf and twinkling candles bathe the proceedings in an almost Gatsby-esque glow. For something less sedate, try salsa lessons and dancing on Tuesday after dinner; most Fridays morph into a wild 1970s disco night (after the free hors d'oeuvres served during happy hour). The legendary Barefoot Man (think a Jimmy Buffett–style expat) performs Saturday. The stunning seaside setting on tiered decks compensates for often undistinguished food and service. The Ports of Call bar is a splendid place for sunset, and tarpon feeding off the deck happens nightly at 7 and 9.