20 Ultimate Things to Do in the Cayman Islands

If there’s one iconic activity on Cayman, this is it. The standard three-hour boat excursion includes stops for snorkeling along the way to Stingray City. But the real thrill is standing in this shallow sandbar, barely three feet deep and the soft translucent green of Murano glass, surrounded by dozens of Atlantic southern stingrays. The remarkable creatures exhibit a balletic grace as they glide around visitors, nosing for food and allowing themselves to be petted. Almost as entertaining are the boat crews, many of them multi-generational families; they explain their favorite rays’ nicknames, tell tales – tall and otherwise – of their exploits, and strum guitars, exhibiting typically warm Caymanian hospitality.

The outdoor exhibits at the Cayman Turtle Centre tell the life story of the glorious green turtles, from hatchlings to lumbering leviathan senior citizens. Kids of all ages especially love the photo ops with the youngins at the touch tanks. But there’s more to the Turtle Centre than amphibians. Sharks glide menacingly through the Predator Reef, iguanas dart around their own enclosures, and colorful birds from around the Caribbean flit about the aviary. You can even sunbathe and snorkel at the artificial beach.

Grand Cayman’s North Side features a string of lovely beaches. The most popular, Rum Point, offers a slightly less frenzied and frenetic day in the sun than the showcase strand, Seven Mile Beach. Lime (meaning chill out) over margaritas or mudslides at the two rollicking beach bars, Kaibo and The Wreck, both of which also dish out decent pub grub. The onsite branch of Red Sail Sports can outfit you for aquatic activities aplenty: parasailing, snorkeling, windsurfing, jet skiing, and more.

Birdwatchers will enjoy a literal field day on all three islands. The multi-hued Cayman Brac parrot is the prize sighting; the Brac even set aside a Parrot Preserve amid an unspoiled tropical hardwood forest. But Grand Cayman features several areas such as the Mastic Reserve, Salina Reserve, and Colliers Pond in the less developed East End that attract over 120 migratory fowl species. And Little Cayman’s once-endangered red-footed booby population numbers 100 times that of its human residents. The Gladys B. Howard Little Cayman National Trust features viewing platforms replete with telescopes to admire the adjacent Booby Pond Nature Reserve, also home to majestic frigate birds, whose impressive wingspan enables their aerodynamic acrobatics.

Brac means bluff in Gaelic: The titular escarpment rises 140 feet at its highest point on the island’s northeastern tip. Intrepid rock climbers have long considered the Brac one of the world’s leading exotic challenges. Until recently, abseiling and rappelling was strictly an “at-your-own-risk” affair; climbers had to bring their own equipment, while the existing bolts along the 100-plus established routes weren’t regularly maintained. Now Rock Iguana, whose founders include world-class climbers, leads expeditions with top-notch gear–plunging from the top of the Brac into the savage surf or spelunking into caves–and helps ensure the holds remain secure and safe. They also offer lessons for beginners.

The bluff is pocked with caves of varying size. Some names like Elevator Shaft hint at the difficulty of access, while others like Buccaneer’s Inn reference the rumors of hidden pirate booty. Fortunately, several chambers have been opened up to visitors. Most are easily accessible, a legacy of olden days when families would take shelter during hurricanes. The infant’s grave in Rebecca’s Cave is a poignant testament to the latter. Bat Cave is less remarkable for its formations than its hanging epiphytes and creepy creatures. Skull Cave received its moniker from the shape of its yawning opening; the vaulted interior features intricate stone gardens and handsome cream-and-black striations.

Grand Cayman’s newest major attraction, Crystal Caves, offers an unexpected treat on this flat island: a labyrinthine network of caverns still being explored, opened, and illuminated. A short hike through the rainforest brings you to a thatched souvenir hut (offering frosty beers and free insect repellent), overlooking an enormous banyan tree crawling up the main entrance. The two caves currently on display feature a vast array of limestone gardens, underground lakes, dazzling examples of flowstone, and fancifully shaped rock formations; the affable guides share some of their nicknames and encourage your descriptive imagination.

Grand Cayman is renowned for the quality of its easily accessible shore dives and snorkeling, circling the entire island. Three prime spots beckon right off “downtown” George Town: Cheeseburger Reef and the adjacent Eden Rock and Devil’s Grotto. All three delight divers and snorkelers with a maze of tunnels and caverns hosting a riotously colored collection of marine life. Eden Rock’s grottoes host the so-called “silver rush” in spring and summer: a shimmering curtain of silversides.

For a small island, Grand Cayman’s population boasts a virtual United Nations not only of accountants and bankers but chefs, too. It’s an international smorgasbord of cuisines, where the kitchen staff might hail from Cambodia and Colombia, bringing their culinary influences to the menus. The savvy savory offerings start with Blue by Eric Ripert where the top toque’s hand-picked team adroitly blends signature dishes from New York City’s Le Bernardin with local ingredients. Crave Italian? Try Agua for everything from superlative ceviches to delectable pastas, the new Bàcaro for sumptuous cicchetti (Venetian tapas), or Luca for classic fare presented with flair and paired with superb wines from an extensive list. In the mood for Indian? The new Pani Indian Kitchen offers a stylish take on sophisticated subcontinental street food.

Local Caribbean craft traditions are slowly dying; thankfully, Brackers such as 84-year-old Annalee Banks have imparted their skill to a younger generation. You can visit Annalee at her home, watching her nimble fingers fly over the plaited dried silver thatch palm fronds. She might even give you an impromptu lesson in how to weave them into stylish and sturdy handbags and hats.

Like any big cruise ship port-of-call, George Town hustles and bustles with duty-free shopping options. You’ll find the usual luxury culprits from Kosta Boda to Breitling and Cartier to Clarins at such elegant establishments as Kirk Freeport. Don’t overlook independent stores like Artifacts for stylish antiques like Spanish doubloons and maps, or Guy Harvey’s for the marine environmentalist’s artworks and signature logo merchandise. If you need a break, pop into the small but superlative Cayman Islands National Museum, set in the former gaol, which offers interactive natural history displays and cool animatronics bringing the islands’ rich history to life.

Located in the middle of Grand Cayman’s less visited East End. Queen Elizabeth II Botanic Park is a wonderful spot to Zen and zone out, strolling through its beautifully curated and kept gardens, ranging from a selection of Caribbean palm trees to orchids. The Blue Iguana Recovery Program also runs fascinating tours, daily (except Sunday) at 11 am, of the small habitat tucked away inside the park. Volunteer student botanists from around the globe act as guides, explaining the endangered blues’ life cycle and the vital breeding program that is slowly replenishing the population in the wild.

With fewer than 200 year-round residents and a handful of villas and small dive resorts, it’s hard not to find solitude on blissful Little Cayman. But biking to Point of Sand or kayaking to nearby Owen Island rewards sun worshippers with gorgeous desolate beaches with powdery sand and gentle sea breezes. The fine snorkeling (and fishing in the flats on Owen) is a bonus.

An expat sculptor and avid diver named Foots has spent over a decade on his grand passion, fashioning life-size statues depicting larger-than-life legends from the Lost City of Atlantis: Elders and Sentinels, a.k.a. priests, lawgivers, and deities. Foots has sunk over 300,000 pounds of material offshore at the former Radar Reef, creating a convincingly mythic and magical sculpture garden wreathed in coral. Though his enormous arch and sundial were toppled by Hurricane Paloma, they’re still fascinating viewing. Driving around the island, you can see his latest works in front of his home (and his friends’ homes), awaiting their ultimate baptism. Chat Foots up at a bar or restaurant and he might just ask you to pose for a sculpture.

The Caribbean has a long tradition of Jimmy Buffet wannabes putting their own spin on Reggae and Calypso music  Barefoot Man, who’s been charming both locals and visitors for two decades, is a classic example of this tradition. Imagine Jimmy Buffett or Brian Wilson meets Bob Marley…after a couple of very strong rum punches. You can catch Barefoot once weekly at both Tides (a.k.a. Pelican’s Reef) and The Wharf. Other regular island performers of note include Lammie (a reggae Elvis) and Hi-Tide.

Perennially voted a Top-10 Caribbean strand, Seven Mile Beach is a mere 6.5 miles long, but its personality changes several times as it unfurls along the coast. The sections on either end, closer to George Town and West Bay, aren’t as expansive but feature superb snorkeling. The larger hotels–Grand Cayman Marriott Beach Resort, The Ritz-Carlton, Grand Cayman, The Westin Grand Cayman Seven Mile Resort & Spa, and the newer Kimpton Seafire Resort + Spa–anchor the central sections, their beach bars and restaurants dictating the ambiance and pace. For a more raucous–bordering on raunchy–beach bar experience, try Calico Jack’s (now part of the Kimpton Seafire Resort + Spa). Or, opt for a more refined tipple at Royal Palms and Luca.

Little Cayman boasts one of the world’s top dive sites, Bloody Bay Wall. Hanging gardens of anemones, gorgonians waving like come-hither courtesans, and pyrotechnically-hued schools of fish await happy divers. While you’ll come face-to-face with groupers that outweigh you (not to mention sharks and barracuda), the wall was named not for predatory attacks but a deadly colonial naval skirmish. Less heralded yet just as striking is the adjacent Jackson Wall, also part of the designated Bloody Bay Marine Park.

For the ultimate in posh pampering without pomp or pretension, check into one of the relaxing retreats along Seven Mile Beach. A trio of tremendous resorts dot Seven Mile Beach, each with its signature look and feel–and rabid fan base: Kimpton Seafire Resort + Spa, The Ritz-Carlton, Grand Cayman, and The Westin Grand Cayman Seven Mile Beach Resort & Spa. All three offer prime beachfront real estate, terrific restaurants, relaxing spas, and more.

One of the best ways to sample a taste of Cayman is at happy hour, when several restaurants offer a tempting tapestry of tapas-style nibbles. Best of all, eateries like Cayman Cabana, The Wharf, and Rackam’s Waterfront also offer live entertainment: from local bands to feeding tarpon, illuminated by the setting sun. It’s one of Cayman’s ultimate photo ops.

For those who want to relive childhood fantasies of The Black Stallion or Black Beauty, galloping through crashing surf along a virtually deserted beach, the horseback riding companies organizing rides along Barkers make a winning proposition. Some outfits such as Pampered Ponies and Cayman Horse Riding even organize an actual swim with the horses. Usually hoofprints in the sand are the only sign of life, aside from the stray wild chicken (your guide will explain). It’s an elemental Robinson Crusoe experience.