The Cayman Islands, with their boundless options for diving, sailing, snorkeling or simply snoozing with a book folded over your nose, are a sound choice for a mid-winter getaway. Located just south of Cuba and northwest of Jamaica in the western Caribbean Sea, they form part of the Greater Antilles archipelago, and are ringed by white sand beaches and aquamarine water. 

You may have noticed your social media feed blowing up with vacationing celebrity sightings lately, and chances are the Cayman Islands are at the centre of the buzz. From Formula 1 star George Russell touching down for the Cayman Cookout and rubbing shoulders with culinary icons like Eric Ripert and Daniel Boulud, to sightings of Hailey Bieber, Emily Ratajkowski, and even rumours of Taylor Swift popping by, this low-key high-minded Caribbean trio of islands has quietly become a magnet for bold face names. 

Grand Cayman in particular is like taking the best parts of a major city – great restaurants, safe streets, nice people and things to see and do – but in a tropical haven. And now, with new direct routes on Porter from Toronto or Ottawa, you can touch down within four hours. 

You may come for total relaxation or an adventurous escape. Me? I went there to eat.

Taco Tuesdays

The stunning new Hotel Indigo is the sister resort of Kimpton Seafire Resort and a hub for some of the best seaside dining on the island. I especially love Coccoloba and its Taco Tuesdays, when the regular taco list doubles and the spicy jerk chicken tacos will blow your flip-flops off. There’s also best-ever elote (street corn smothered in cheese, mayo, chile, garlic, cilantro and lime), ceviche with plantain and tortilla chips and a bevy of margarita options. Everything you want from beachside dining – tiki torches, ocean views and easygoing vibes – is on the menu.

The Healing Meal

Maureen Cubbon, a former Vancouverite, is the wellness and culinary director at Nourish at VIDA in West Bay, a boutique hotel and retreat where mind, body and soul are embraced through programming and food – think ferments, spices and especially juices. One of the biggest travel trends is going away for a full-body reset, and you can find that here. Start slow, with juice. The Immunity juice blends apple, carrot, orange and ginger, while the Antioxidant combines beet, carrot, apple and lemon. Mix the two and you’ve got the Be Well, which tastes like a perfect blend of health. But it’s not about deprivation: there are beef tacos simmered with onions, peppers, tomatoes, hot sauce and Worcestershire, açaí smoothie bowls, poke bowls and Seaside Caesars. My Nourish Benny – soft-poached eggs with Scotch bonnet hollandaise over arepas with callaloo and pumpkin mash – had me feeling better already.

The Knockout Splurge Blue by Eric Ripert, the only AAA Five Diamond restaurant in the Caribbean, delivers fine French cuisine with tropical flair. Perfectly calibrated – formal yet fun – it’s supremely delicious. Tables are spaced like a Michelin three-star, with service nearly one-to-one. A Vesper martini from the tableside bar cart, prepared by the talented mixologist, Prikash, isn’t just a show; it’s so smooth, it’s like drinking ice water. The tasting menu is fish- and seafood-focused, and every sauce is better than the last. Think mildly barbecued lobster with zucchini and lobster roulade, crispy chickpeas and béarnaise, and pan-seared monkfish with charred avocado, cilantro, chayote and pasilla sauce. After four courses come the pre-dessert, dessert and post-desserts. Best bite of the meal? The hamachi. Who am I kidding? The martini!

True Local Flavour

The colourful seaside shack called Heritage Kitchen, next to Boggy Sands Road in West Bay, dishes out traditional Island specialties such as conch fritters, curried Mahi, panfried escovitch and coconut grouper, with much of the fish caught in sight of the rustic hut and picnic tables. Passionfruit juice flows alongside plated lunches of things like coconut-scented rice, creamy coleslaw and tender lobster tails in a tomatoey onion sauce, or snapper escabeche with fry bread – all cooled by ocean breezes and industrial fans.

Food Truck Fare

Located in the parking lot of a car wash, Murph’s Kitchen is all about fish and fritters, sandwiches, tacos and sides. There’s incredible shredded oxtail with sweet nubbins of plantain tucked into soft coco bread, plus a hefty side of cassava fries – crispy outside, soft inside – and breadfruit fries with garlic mayo for dipping. Eaten at picnic tables while fresh coals are fired up on a nearby drum smoker to make more jerk, I was as hot as I was happy – and I came this close to walking through the car wash.

Lunch with Flair

Saint June at The Ritz-Carlton offers a relaxed, alfresco beachfront vibe and a taste of the good life. I heartily recommend the freshly caught, thick-as-a-deck-of-cards grilled snapper fillet on a brioche bun with citrusy cucumber salad, aji amarillo aioli, the crispiest fries and a Diet Coke. My idea of paradise. Add incredible service and soft breezes, then top it off with a massage at the newly renovated Ritz-Carlton Spa, Grand Cayman, and you’ll be floating on a Caribbean cloud.

Sunset Sips and Snacks

The best spot for bites and cocktails as the sun goes down is Pom Pom Rooftop at the Hotel Indigo – the island’s first and only rooftop lounge and restaurant. Latin flavours meet local products in shared snacks and playful plates. The pão de queijo (cheese puffs) with guava butter are a must, as is crunchy squid and cancha (toasted corn kernels) with leche de tigre (the zesty Peruvian “tiger’s milk” of  lime, fish stock, peppers and cilantro) for dipping. There’s also chilled octopus carpaccio, aji-spiced lamb balls and tenderloin skewers cooked over Colombian charcoal. Big flavours, great cocktails and, if you’re lucky, you might just spot the green flash.

Award-Winning Cocktails

There are standout bars on the island, thanks to a gaggle of former global brand ambassadors and World’s 50 Best mixology winners who have chosen to settle here, launching sophisticated concepts like the literary themed bar,  Library by the Sea (also a Top 50 recipient). You won’t meet a more passionate general manager than Jim Wrigley, who takes as much joy in developing cocktail concepts as he does in building the bar’s library of books. I had the Dancing Clown, inspired by Stephen King’s It: more drinkable than scary, with bourbon, peanut butter, strawberry caramel, banana liqueur, oloroso and tannin. A beautiful room, perfect little snacks and polished service make it a wonderful place to be.