Discover the dreamy resorts and local-favorite cafés worth a spot on your itinerary.
For many, the words “go to your happy place,” call to mind a destination resembling the Cayman Islands. With stretches of white sand lining turquoise water, it’s the type of place that ruins other beaches for you.
“The Cayman Islands are the ultimate blend of adventure, relaxation, and luxury, especially Grand Cayman [the largest of the three islands],” says luxury travel advisor Susan Darcey. They’re also easy to get to from the East Coast — flights from Miami don’t exceed two hours — and stay pleasantly warm year-round. The destination is most popular from November to April, with a quieter off-season lasting from June to August, according to Aaron Sutherland, founder of Jetsetter Lifestyle.
The islands’ line-up of hotels, restaurants, and excursions only adds to its lure. Below, travel experts detail the attractions that stand out.
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Hotels
Kimpton Seafire Resort + Spa
Kimpton Seafire Resort + Spa is known for its infinity pool, sunlit terraces, and full-service spa, says Sutherland. “Located on Seven Mile Beach, it’s in one of the best spots for avoiding crowds and viewing incredible sunsets,” Darcey adds. “Most rooms offer ocean views with floor-to-ceiling windows and balconies that overlook the turquoise water.” For those who want added space and seclusion, the hotel has free-standing beachfront bungalows complete with living and dining rooms.
Palm Heights Grand Cayman
With an interior inspired by ‘70s mansions, Palm Heights is an aspirational mood board come to life. Yet the five-star hotel remains understated, with “no grand sign out front, just a quiet nod to the experience that awaits,” says LaDell Carter, founder and lead travel designer at Royal Expressions Travel. Palm Heights has plenty to offer beyond its suites, like a spa with an outdoor hammam, infrared sauna, and plunge pools.
The Ritz-Carlton Grand Cayman
Sutherland’s recommendations include the Ritz-Carlton Grand Cayman, thanks to its private cabanas, personalized service, La Prairie spa, and golf course. It’s a family-friendly resort, with kid-approved attractions like Jean-Michel Cousteau's Ambassadors of the Environment tour showcasing Grand Cayman’s natural beauty.
Dining
Tillies
Darcey considers Tillies at Palm Heights one of the best dining options across the Cayman Islands, citing its creative cocktails and stylish decor. The extensive menu is a tour of the Caribbean, spanning seafood, curry dishes, and vegan options featuring local produce.
Jessie’s Juice Bar & Cafe
Husband and wife Lachlan and Jess Hewitt opened Jessie’s Juice Bar & Cafe hoping to introduce a food-as-medicine approach to the Cayman Islands dining scene. The couple put care into the details, from importing ceramic cups from New Zealand and Australia to sourcing ingredients from nearby farms. “Locals and visitors alike flock there for fresh-pressed juices, plant-based bites, and a menu that celebrates sustainable, organic ingredients,” says Carter.
Calypso Grill
Calypso Grill is “an institution in Cayman dining,” that’s known for its local cuisine and has gorgeous views, Sutherland says. Expect fine-dining cuisine in an atmosphere that’s more charming and genuine than stuffy. Be sure to opt for outdoor seating and save room for the restaurant’s sticky toffee pudding, a dish that’s famous among foodies.
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Activities
Cayman Kayaks Bioluminescent Tour
You can fill your schedule with beach time, spa appointments, and al fresco dining, but the islands’ bioluminescent tours offer something a little more unique. “On the guided adventure, you’ll kayak or take an electric boat to one of the island’s glowing bays, where tiny organisms light up the sea with an ethereal blue glow when disturbed by movement in the water,” Darcey says. Note, the company operates its night-time tours only a few weeks out of each month, since the glowing organisms are most visible on the darkest nights of the moon.
Private Pilates at Palm Heights
Palm Heights’ gym, Palm Heights Athletics, is home to personal training, workshops, retreats, and group classes. Carter recommends booking a private Pilates session with Baylee Saltmarsh in particular. “Known for her focus on form and personal connection, Baylee delivers a wellness experience that rejuvenates both body and spirit,” she says. Saltmarsh’s signature “BBB Method” fuses classical Pilates with functional movement.
Stingray City Sandbar Snorkeling
This tour allows you to get up close and personal with the island’s wildlife. “You’ll take a scenic boat ride to the shallow sandbar and wade into the waist-deep water with your guide,” Darcey says. “As you move through the water, the rays swim alongside and sometimes even circle around you, lightly brushing up against you.” The company also puts on private tours and turtle encounters.