7 Best Nightlife in Cayman Islands

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.

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.

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 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.