Caribbean Resurgence: Grand Cayman

Jun 05, 2024

MILES FROM CHARLOTTE: 1,099

TRAVEL TIME: 2-hour, 42-minute flight

As we approach the turquoise waters of Stingray City and drop anchor at the sandbar, about 40 hula hoop-sized, gently flapping sea pancakes surround our boat. Stingrays have poor eyesight, our guide explains, so they’ll probably graze your legs once you hop into the water. “Try not to make any loud noises or shuffle your feet,” he says. “It startles the stingrays.”

I ease into the waist-deep water and feel something rubbery bump the back of my knees. I squeal and bounce on my tippy-toes. The guide shakes his head and smiles. Rookie move.

Stingray City is a series of shallow sandbars in the North Sound of Grand Cayman, where dozens of southern stingrays swim right up to you and allow you to feed, pet, and photograph them. They’re common in the calm waters off Grand Cayman, and they hang around this sandbar because it’s a good place to get a snack when fishermen return with the day’s catch. These bottom-dwelling fish use the barbs on their tails only in defense, so they’re unlikely to sting you. (Steve Irwin was killed by the larger and far more dangerous short-tail stingray, which is endemic to Australia.) And, the guides advise, kissing a stingray brings you seven years of good luck.

Stingray City (above) is a group of sandbars 25 miles off the shore of Grand Cayman. Photos Courtesy COYNE PR

I’ve made it this far, I think. The guide takes my hand and runs it over the 50-pound female’s leathery skin to get us formally acquainted. Then he slowly moves both my arms beneath the stingray and instructs me to lift her toward my face. Once I’ve got a steady hold on my new friend, he lets go and tells me to give her a smooch. This time, I do as I’m told.

The Cayman Islands may sound like a far-off destination, but a flight from Charlotte to Grand Cayman is less than three hours, or the equivalent of flying to Dallas. You touch down on Owen Roberts International Airport’s single runway, and a reggae band plays as you walk to the terminal. This is the time to peel off your jacket, put on your sunglasses, and breathe the warm island air.

Grand Cayman is the largest of a trio of islands between the Yucatán Peninsula and Jamaica. (Cayman Brac and Little Cayman are the other two.) About 68,000 people live here, and expats outnumber native Caymanians two to one. The bright orange flowers of poinciana trees line the streets, but you won’t see factories or mills. “Everything’s imported here,” my driver quips, “including y’all.”

In recent years, Grand Cayman has developed a reputation as the culinary capital of the Caribbean. With more than 130 nationalities living on the island, the mix of cultures translates to dishes like coconut ceviche, plantain flatbread, and prosciutto-wrapped snapper. The drinking age is 18, but you won’t find throngs of college kids like it’s spring break in Cancún. You’re more likely to see paddleboarders, snorkelers, and scuba divers alongside the luxury yachts that dot the shoreline. It’s developed—the roads are paved, well maintained, and mercifully easy to navigate—but not jammed, South Beach-style, with high-rise condos and hotels. You’ll need a passport, but it’s one of the easiest international trips you’ll ever take.

Seven Mile Beach (7MB, as the locals call it) is a crescent of white sand on the island’s western end and the area that attracts the most visitors. The Kimpton Seafire Resort + Spa has 266 rooms, 55 private residences, and six beachfront bungalows. The Ritz-Carlton, Grand Cayman offers everything you’d expect from a Ritz: a spa, poolside and beachfront cabanas, five on-site restaurants, and Starfish Cay, a family-friendly water park with splash pads and waterslides. The Westin Grand Cayman Seven Mile Beach Resort & Spa has a sparkling outdoor pool with a swim-up bar, cushioned beach cabanas, and one of the best weekend brunches on the island. If you come with a large group, Black Urchin has four-bedroom suites and private residences that can sleep up to 22 people. The 2.5-acre property also has a private beach, pools, and a chef who can prepare customized dinners with wine pairings.

The Kimpton Seafire Resort + Spa

The Ritz-Carlton has six on-site restaurants and bars, two outdoor pools, a spa, and a helipad.

“Bottomless brunch” is a sacred institution on Grand Cayman and a Sunday standard at most hotels along 7MB. Ave, inside The Kimpton, has a staggering spread of fresh seafood and hand-rolled sushi, carving stations, a pasta bar, and a wall-to-wall dessert display. The Westin’s version is equally decadent and tastes even better on the patio with a mimosa. For a no-frills lunch, stop by Chicken! Chicken!, a counter-serve eatery that slings huge rotisserie chickens in marinades of herbs, spices, and citrus. Don’t be alarmed if you see chickens roaming the parking lot (they run wild across the island) or hear an employee refer to this spot as “parking lot-to-table” (they’re kidding). Have a light lunch or afternoon cocktail at Ms. Piper’s Kitchen + Garden, a local favorite that’s tucked in a tropical backyard in George Town. Enjoy a family-style lunch or dinner at Thatch & Barrel on the oceanside cliffs of Pedro St. James, where you can sample local rum and feast on Drunken Mussels and Jerk Chicken. For an upscale dinner, book a table at Nova, a beachfront restaurant on the north shoreof West Bay.

Nova serves Mediterranean-Japanese dishes like Miso Steak and Prosciutto Wrapped Snapper.

Stingray City Cayman Islands provides daily shuttle service from the Seven Mile Beach resorts to the George Town Cruise Ship Port Terminal, where a 20-minute boat ride takes you to the sandbar. It’s a big draw for tourists but lives up to the hype. For more fun on the water, rent a stand-up paddleboard through Kitesurf Cayman or Cayman Stand Up Paddle Co. and have it delivered to you anywhere on the island for as many days as you want. If you stay at The Westin, rent paddleboards or kayaks by the hour at Red Sail Sports. Take a guided tour of Pedro St. James Castle, the oldest surviving stone building on the island, to learn some Grand Cayman history, including the story behind its tax-free status (see sidebar on next page). The property has been open to the public since the 1990s, when the Cayman government took ownership and restored it with 18th-century furniture and artifacts. If you bring young kids, visit The National Gallery of the Cayman Islands on Saturday, when the museum hosts free family day, and do art projects inspired by the museum’s current exhibition. For a good laugh, go to Hell (seriously, that’s what it’s called), an area in West Bay marked by eerie patches of black limestone. Stop by the gift shop, say hi to Bonnie (“Clyde’s buried in the back,” she says), and purchase shot glasses, hats, T-shirts, or a postcard for just 25 cents. Then, do as Bonnie says and drop it like it’s hot … in the mailbox.

Pedro St. James Castle was built in 1780. The property has been open to the public since the 1990s, when the Cayman Islands government took ownership and restored it with 18th-century furniture and artifacts.

Hell is a unique natural wonder in West Bay marked by jagged, black limestone formations.

The story has been passed down through generations for more than two centuries, so details vary depending on who you ask. But legend has it that one stormy night in 1794, the Cordelia, the lead ship of a convoy of 10 merchant ships returning to Britain from Jamaica, wrecked off the east end of Grand Cayman. The Cordelia sent a signal to warn the other ships, but it was too late. The other nine ships sailed into the reefs. The Caymanian residents came to their aid and saved the majority of the passengers, including a son (some sources say a nephew) of King George III. To show his appreciation, the king granted the islands freedom from military service and taxation. Grand Cayman remains one of the world’s leading offshore financial centers.