This expat-filled, Canadian-favourite winter destination is planting a flag on the world-class bar map. With pretty perfect daily weather and literally a Seven Mile Beach to enjoy during the day, and plenty of sunset and nightlife spots, there’s no need to wait until Cayman Cocktail Week (an annual festival, in the last week of October) to visit.
Start with sunset drinks and early cocktails, as Cayman bars close at midnight, with last call often well in advance. Watch for exciting new hotspots, like the just-opened Vines 2 Ocean (V2O), a wine, oyster and charcuterie bar; and the area’s first rooftop bar at the Hotel Indigo Grand Cayman (open to guests here and at the sister Kimpton Seafire), accepting bookings now for its projected April 2024 opening. Spirits nerds will want to take in a tour and tasting at Cayman Spirits Co., co-founded by Cayman-Canadian Walker Romanica, and the home of Seven Fathoms underwater-aged rum.
The Global Contenders
Dubbed “Already the Best Bar of 2024,” Library by the Sea at the Kimpton Seafire Resort + Spa has assembled a pro team from around the globe and a high-concept menu of literary-inspired drinks, with elements concocted in a pool house-turned-tech-lab, complete with Rotovap and 3-D printer. After making a splash last year with its sci-fi “drink” based on Blade Runner’s Philip K. Dick origin story (Electric Dreams arrives as two tubes of Scotch-based paste, gel cubes and bright, flavourful powders on a circuit board), it’s launching its second menu soon. Signature sips include For Cayman With Love, a Martini-like riff based on cane spirit from a Cayman distillery, infused with local herbs and sipped from an elegant ceramic shell made by local artists. You can look through first-edition books, a vintage-spirits list and even drink an E. Hemingway Special, a Daiquiri as Ernest would have enjoyed it, made with circa-1930s spirits.
Located within the Grove condo and retail complex, Door No. 4 recently landed on the 50 Best Discovery arm of the World’s Best Bars list. On the list of a tight dozen or so house cocktails (plus a bartender’s choice chalkboard of suggestions), the no-and-low alcohol drinks stand out for being made with the same advanced techniques and flavours as a full-proof drink like A Jamaican in New York (a Manhattan riff made with rum, cognac, walnut liqueur, house vermouth and pear-like local naseberries). The non-alc New Beau, for instance (purple corn, cacao, coconut, pineapple skin, sarsaparilla, coriander seed and oak extract), allows people to enjoy something that looks like a glass of wine, “and be quite discreet about it,” one bartender says.
Also on 50 Best Discovery is Next Door, at the upscale Crescent retail and marina complex. Though it’s hard to resist the waterfront outdoor patio, the long, narrow interior has the siren call of live entertainment and drinks bright with local herbs and botanicals. Try a refreshing Compass highball using bitter taraxacum, infused into a white Port and cachaça highball with cantaloupe and dandelion soda.
Within the Beverly Hills vibes of the Palm Heights boutique hotel, Tillie’s restaurant’s beach bar is the chic place to sip with sand between your toes. Trade glances between the sunset and an equally fascinating golden-hour fashion shoot on the beach, while sipping signature cocktails like a White Negroni made with minerally Salers Aperitif, or a Tillies Rum Fashion, which combines roasted-pineapple rum and sesame with bourbon in a split-base OF.
Best known for founding the annual Cayman Cookout culinary festival every January, the Ritz-Carlton Grand Cayman lobby bar, the Silver Palm, has rich leaf-green walls and a back bar glowing with elite rum, agave and whisky bottlings. Honour the Silver Palm’s traditional afternoon tea with the Oolong Euphoria cocktail (rare oolong tea with Woodford Reserve bourbon, vermouth and amaro, plus a kiss of apricot and pandan). The real treasure sits in a custom-built wooden wardrobe, which holds a selection of top rums, cigars and Caribbean cacao products — the makings of many happy hours during your visit.
Say “dive bar” to a Canadian and conjure images of neon beer signs, peeling walls and the smell of stale pitchers. On Grand Cayman, think wetsuits and ocean-fresh swimmers flip-flopping up to a topical outdoor bar. Macabuca, at the north end of the West Bay, is so close to the action waves frequently crash up on its rocky borders. With heaping plates of casual food plus tiki and party drinks like a frozen Raspberry Blastoff (a vodka, raspberry and lime mini-pitcher, served with a Red Bull), you might not expect the white-linen crowd to congregate here. But upstairs is the Cracked Conch, a top-notch restaurant with its own elegant (air-conditioned, indoor) bar, with tiki takes on classic cocktails (like the Man on Fire, a mango Marg with spicy peppers).
Other oceanside watering holes include Rackam’s Waterfront Restaurant & Bar, named for a onetime pirate; and fried-chichen haven The Bird. If you have a pal with a boat, or an hour to take the passenger ferry from Caymana Bay, head to Rum Point Beach Club to put your toes in the sand on the other side of the island.
Smokers, rejoice: there is an indoor haven for you on Grand Cayman, called Backroom. A humidor of Cuban cigars complements top-shelf whisky (like a full range Yamazaki, fine Cognac and Old Rip Van Winkle bourbon, better known as Pappy). The full frontal assault of second-hand smoke isn’t for everyone, but even non-smokers will enjoy a smoky drink like the Talisker-based Skye High. Though sports play on the big screens and there’s an undeniable bro-vibe, the clientele was half women when we visited.
Post-shift, you’ll find the island’s finer palates gathering at Le Petit Bar, a wine-forward (three dozen curated pours by the glass) bar where you might be greeted by a welcome shot of chilled, house-made West Bay ‘cello, limoncello infused with LPB’s basil and other garden herbs. Sample back bar gems like Depaz Agricole rum or Gota Gorda mezcal (the project of former Vancouver bartender Dani Tatarin), and assemble your own DIY board from charcuterie, cheese, bread, fruit and nuts.
—by Charlene Rooke