Cayman Islands
We’ve compiled the best of the best in Cayman Islands - browse our top choices for the top things to see or do during your stay.
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1. Macabuca Oceanside Tiki Bar
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...
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 (CI$9 jerk dishes weekends; Monday all-night happy hour, DJ, and CI$17 all-you-can-eat barbecue) lure everyone from well-heeled loafers to barefoot bodysurfers animatedly discussing current events.
857 N.W. Point Rd., West Bay, Grand Cayman, KY1-1201, Cayman Islands345-945–5217 -
2. South Coast Bar and Grill
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...
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.
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3. South West Collective
A celebration of all things mixology, South West Collective occupies a prime second-floor spot with a patio and enormous picture windows overlooking the harbor. The...
A celebration of all things mixology, South West Collective occupies a prime second-floor spot with a patio and enormous picture windows overlooking the harbor. The convivial hangout offers board games, live music on Friday (and DJs spinning genuine vinyl), and a trendily loungy but unpretentious ambience. The pub fare comes at fair prices, whether lunch or such bar bites as smoked oyster dip goosed with lemon and capers or spiced beef patties with rum barbecue sauce. But the drinks are the thing, from loose-leaf teas to global artisan beers, homemade sangria or kombucha smoothies to craft cocktails (as well as the house moonshine).
S. Church St., George Town, Grand Cayman, KY1-1003, Cayman Islands345-946–3004 -
4. The Bar at Ave
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...
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.
60 Tanager Way, Seven Mile Beach, Grand Cayman, KY1-1303, Cayman Islands345-746--4111 -
5. West Indies Wine Company
At this ultra-contemporary wine store, purchasing tasting cards allows you to sample any of the 80-odd wines and spirits, available by the sip or half...
At this ultra-contemporary wine store, purchasing tasting cards allows you to sample any of the 80-odd wines and spirits, available by the sip or half or full glass via the argon-enhanced "intelligent dispensing system." Selections traverse a vast canny range of prices, regions, styles, and terroirs. The enterprising owners struck a deal with neighboring restaurants and gourmet shops to provide appetizers or cheese and charcuterie plates, best savored alfresco at the tables in front of the handsome space. Small wonder savvy locals congregate here after work or a movie at the nearby cineplex.
Corner of Market St. and the Paseo, Camana Bay, Grand Cayman, Cayman Islands345-640–9492 -
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6. Backroom
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....
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.
672 W. Bay Rd., Seven Mile Beach, Grand Cayman, Cayman Islands345-947--7666 -
7. Barracuda's Bar
New Yorker Terry Chesnard built his dream bar from scratch, endowing it with an almost 1960s Rat Pack ambiance. Nearly everything is handcrafted, from the...
New Yorker Terry Chesnard built his dream bar from scratch, endowing it with an almost 1960s Rat Pack ambiance. 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.
20 West End Rd., Creek, Cayman Brac, KY2-2301, Cayman Islands345-948–8511 -
8. Cayman Cabana
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...
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.
N. Church St., George Town, Grand Cayman, KY1-1109, Cayman Islands345-949–3080 -
9. Coconut Club
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...
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 Tillie’s, 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.
747 W. Bay Rd., Seven Mile Beach, Grand Cayman, Cayman Islands646-809--7256 -
10. Coconut Joe's
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,...
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.
West Bay Rd., Seven Mile Beach, Grand Cayman, KY1-1201, Cayman Islands345-943–5637 -
11. Fidel Murphy's Irish Pub
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...
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).
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12. Hard Rock Café
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...
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.
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13. La Esperanza
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...
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.
The Creek, Stake Bay, Cayman Brac, KY2-2001, Cayman Islands345-948–0591 -
14. Legendz
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...
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.
West Bay Rd., Seven Mile Beach, Grand Cayman, KY1-1204, Cayman Islands345-943–3287 -
15. Lone Star Bar and Grill
Calling itself Cayman's top dive (some might call it a shrine to Texas and alcohol), this bar is defined by its vast sports memorabilia collection,...
Calling itself Cayman's top dive (some might call it a shrine to Texas and alcohol), this bar is defined by its vast sports memorabilia collection, nearly 30 big-screen TVs tuned to different events, and excellent margaritas. Trivia and Rock 'n' Roll Bingo nights lasso locals.
686 W. Bay Rd., Seven Mile Beach, Grand Cayman, KY1-1202, Cayman Islands345-945–5175 -
16. My Bar
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...
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. They offer great grub, and the crowd is a mischievous mix of locals, expats, and tourists.
Sunset House, S. Church St., George Town, Grand Cayman, KY1-1106, Cayman Islands345-949–7111 -
17. Rackam's Waterfront Pub and Restaurant
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...
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's complimentary snacks on Friday and pub fare at fair prices until midnight.
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18. Silver Palm Lounge
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...
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 postdinner 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.
West Bay Rd., Seven Mile Beach, Grand Cayman, KY1-1209, Cayman Islands345-943–9000 -
19. The Attic
This chic sports bar has three billiard tables, classic arcade games (Space Invaders, Donkey Kong), air hockey, and large-screen TVs (nab a private booth with...
This chic sports bar has three billiard 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 $25 initiation (with T-shirt and personalized leather wristband, toga optional) and $10 weekly activity fee, you're shuttled by bus to three different bars, with free shots and drink specials.
West Bay Rd., Seven Mile Beach, Grand Cayman, KY1-1006, Cayman Islands345-949–7665 -
20. The Beach Bar
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...
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.
2221 Queen's Hwy., East End, Grand Cayman, KY1-1204, Cayman Islands345-947–3100
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