22 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.

This Caribbean beach bar and popular cocktail lounge draped in white linens sits on the shores of Seven Mile Beach. Hailing from the creators of Tillies, the Coconut Club offers bar bites and aperitifs with vegan and vegetarian options. Soak up the sun on a lounger out front, shade yourself at the marble shell-clad bar, or wait until night when the DJs spin records on the sand and the locals come out to play.

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.

Thanks to the unusual logo (a stogie-smoking Castro surrounded by shamrocks) and congenial Irish wit and whimsy, you half expect to find Raúl and Gerry Adams harping on U.S. and U.K. policy over a Harp. The Edwardian decor of etched glass, hardwood, and brass is prefabricated (constructed in Ireland, disassembled, and shipped), but everything else is genuine: the warm welcome, the ales and cider on tap, and the proper Irish stew (the kitchen also turns out conch fritters and lamb vindaloo). Sunday means all-you-can-eat extravaganzas (fish-and-chips, carvery) at rock-bottom prices. Trivia nights, happy hours, and live music lure regulars during the week. Weekends welcome live, televised Gaelic soccer, rugby, and hurling, followed by karaoke and craic (if you go, you'll learn the definition).

Grand Cayman's Hard Rock replicates its 137-odd brethren around the world, especially on the weekends, only with more specialty drinks (try the Orangelicious margarita with Monin pomegranate and blood-orange juices) to complement its extensive burger selection. A 1960 pink Cadillac, a Madonna bullet bra, and rotating memorabilia (gold records, costumes, guitars, and autographed photos from Elton John, Korn, John Lennon, U2, and *NSYNC) are the decor.

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.

Pat's (previously Bucky's) is popular for its all-you-can-eat West Indian lunch buffets. But the real allure is free Wi-Fi and the cushy (if frayed) lounge adjacent to the restaurant, which resembles a small Vegas sports bar with leather armchairs, black-and-white photos, and team pennants and jerseys galore. Open until 11.

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.

The Silver Palm drips with cash and cachet, with a model waitstaff and chic clientele. There's an old-fashioned, leather-clad bar and another section that replicates a classic English country library (perfect for civilized, proper afternoon tea or a pre- or post-dinner Champagne or single malt). Also on tap: fab cocktails, including specialty martinis (the Silver Palm cosmopolitan is a winner: Ketel One citron, triple sec, a squeeze of fresh lime juice, and a splash of cranberry topped off with Moët Champagne); pages of wines by the glass; and an impressive list of cigars, cognacs, and aged rums.

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.

This pub overflows with good cheer and strong drinks. The mudslides are particularly potent, and there are usually some good Cubanos. The alfresco, split-level bar (great water views from the top) serves excellent pub grub (jerk chicken pizza, Caesar salad wrap, portobello-and-Swiss cheeseburger, messy and marvelous spareribs, tempura shrimp) for around C$10 a dish. It's the kind of casual, congenial hangout where almost everyone ends up buying a round at some point. Stop by for Tuesday bingo, Wednesday karaoke, or Friday barbecue with live music, which attracts large, enthusiastic crowds.