9 Cayman Islands Resorts | Where To Find Your Caribbean Outpost

When Kimpton Seafire Resort + Spa debuted on Seven Mile Beach in late 2016, it made waves for being Kimpton’s first Caribbean outpost, Grand Cayman’s first boutique design hotel, and the first new resort built on the island in a decade.

After checking in, it’s time to claim your spot: beanbag chair on the lawn, luxe pool cabana, or a beach lounger. If you need an intermission, munch on chips and guacamole with margaritas at the resort’s Coccoloba Bar & Grill, set right in the sand. More indulgence is on tap at The Spa at Seafire, featuring a hammam (Turkish bath) and a hot-tub grotto dappled with sunlight from above. At sunset, see where the resort gets its name by cozying up in a funky “clamshell” beach bed to watch the sky ignite.

If there’s one brand that screams “beach vacation,” it’s Jimmy Buffett’s Margaritaville. And at Margaritaville’s Grand Cayman address, you can search for your lost shaker of salt right on famed Seven Mile Beach. Fresh from a major renovation in 2018, the resort flaunts a shiny island-escapism aesthetic—accented with palm trees and parrots, of course.

A trip here isn’t complete without polishing off a cheeseburger in paradise. At Eating House 1503, Roy Yamaguchi’s first Caribbean venture, it’s made with certified Angus beef, Swiss cheese, shiitakes, and bacon jam. Just down the street, The Wharf Restaurant & Bar offers a more traditional dining experience (hint: Save some scraps to feed the tarpon waiting in the water below the deck).

Thanks to a $16 million renovation that wrapped in 2014, Grand Cayman Marriott Beach Resort is a five-acre Seven Mile Beach resort that went from generic big-brand hotel to breezy-chic beach house in one fell swoop. Set foot into the airy lobby and you’re surrounded by natural tones, weathered woods, and nautical touches.

If it’s Instagram moments you’re after, you’re in luck. Guests can snap selfies with a freshly cut coconut, a boardwalk-inspired gelato cart, a vintage-style beach cruiser, or an oversize woven egg chair. Handcrafted cocktails shine here; belly up to the poolside Vista Bar for a Cayman Lemonade mixed with house-made syrups and infusions.

The open-air Veranda restaurant is another highlight. The Wednesday-night all-you-can-eat Lobster Fete is a shellfish-lover’s dream accompanied by live music and ocean breezes. Bonus: After a full day of play, there’s no better feeling than drifting off to sleep snuggled into plush Marriott Revive bedding.

There’s more to Grand Cayman than Seven Mile Beach, and Wyndham Reef Resort is proof. Offering the island’s only all-inclusive meal plans, this beach getaway in the quieter East End area is a solid mid-range option for the flip-flop-optional crowd.

Water sports take center stage here, from mild (snorkeling, paddle boarding) to wild—bioluminescent kayak tours, guided Jet Ski excursions, and heart-pumping rides on the Jetovator. The resort’s remote location also puts it closer to island attractions like the Blowholes (a scenic spot where waves explode through vents in the rocky shore), the Queen Elizabeth II Botanic Park, and the Blue Iguana Nature Reserve, which protects this unique endangered species. After all the excitement, refuel with fresh fish and a fruity drink at the resort’s laid-back Beach Bar.

Since opening in 2006, The Ritz-Carlton, Grand Cayman has comfortably presided over Seven Mile Beach as the grand dame of Grand Cayman luxury beach resorts. Inside the 365 rooms and suites, guests are spoiled with private balconies, marble bathrooms, down bedding and nightly turn-down service. The pampering continues at La Prairie Spa (try the 90-minute Gifts from the Sea treatment featuring a seaweed mask and a Swedish massage) and Blue by Eric Ripert, the only AAA Five Diamond restaurant in the entire Caribbean.

If all that sounds a little too formal, you’re getting the wrong impression, because family fun—from outdoor movie nights and an eco-themed kids’ club to the interactive Starfish Cay spray ground—is the true heart of the property. And with a bevy of complimentary beach toys like paddle boards, water tricycles, kayaks, floaties, paddle boats, and water hammocks, don’t be surprised if you discover your own inner child too.

Hosting beach barbecues, beach yoga, beach games and more, The Westin Grand Cayman Seven Mile Beach Resort & Spa takes full advantage of its enviable setting along the widest stretch of the Seven Mile coastline. Check the resort’s calendar for what’s on: Competitive types can participate in activities like guided runs and trivia nights, while kids can make arts and crafts or enter a sandcastle-building contest. R&R-minded guests prefer to loll in the island’s largest pool, where the swim-up bar cranks out dangerously sweet Cayman Mamas.

Toast to the sunset at Tortuga Beach Grill & Bar, where happy hour and live music kick off at 5 p.m. daily. After dark, stargaze with a telescope and night-sky map, or gather around a beach bonfire to roast marshmallows, complete with every s’mores topping imaginable. Even sweeter—the resort unveiled a $50 million renovation in late 2017, so everything has that new-resort smell.

Most vacationers don’t come to Cayman to get away from literally everything, but the few who do will find just what they’re craving at this isolated retreat on the East End. Strategically located at the farthest point away from Seven Mile Beach and George Town, the island’s bustling capital, Compass Point Dive Resort is within a quick boat ride of the area’s 55 acclaimed dive sites. Swim among sea turtles, eagle rays, reef sharks, and Nassau grouper at thriving spots like Jack McKenny’s Canyons. Then, cruise right back to the resort’s own dock for top-side pastimes like hiking the 2.3-mile Mastic Trail. (Night dives and lion-fish hunts are also available.)

A two-minute drive up the road from the resort, Tukka Restaurant and Bar serves up fresh daily catch like spiny Caribbean lobster and ginger mahi-mahi. Request a table outside on the deck to watch night fall over the coast and the Wreck of the Ten Sails.

With 37 high-end, individually owned condos overlooking Seven Mile Beach, Caribbean Club combines the best aspects of a boutique hotel and a private vacation home. Choose from one-, two- and three-bedroom villas, some of which are as big as 2,700 square feet, while enjoying resort amenities like housekeeping service and free oceanfront cabanas.

Luca, the onsite trattoria, earns rave reviews for its Italian cuisine and 5,500-bottle wine list. A 15-minute walk south brings guests to more than a dozen additional dining options at Camana Bay (try the progressive dinner–style Flavour Tour on Wednesday nights). If you want a little break from the quiet, refined vibe of the hotel, ask the concierge staff to arrange a hair-raising helicopter ride over the Caribbean Sea—the water clear enough that you can see starfish from the sky.

For a homey feel at a more modest price point, opt for this North Sound Holiday Inn Grand Cayman resort, where suites come with a fully equipped kitchen, a living room, a dining room, and a washer and dryer. Start the day at the resort’s Blue Iguana Grill, whose breakfast favorites include piña colada French toast and Cayman’s “best pancakes,” served with Ghirardelli chocolate and roasted banana. Later, take advantage of the property’s free shuttle and peaceful pool.

A 15-minute drive north, the Cayman Turtle Center entertains visitors with turtle encounters, an aviary, a butterfly garden, and more. Also nearby, Calypso Grill at Morgan’s Harbour is the place to get your fill of local seafood, including ceviche, stone-crab claws, and cracked conch.