Panorama of paradise beach - Cayman Islands

How to Spend a Perfect Day in Grand Cayman

Looking for up-close encounters with beautiful wildlife? Pristine beaches? Incredible Caribbean cuisine? The biggest isle in the Cayman Islands—just an hour's flight from Miami—has it all. Here's how Jetsetter tastemaker Monica Walton spent a perfect day in Grand Cayman.

Senior Editor, Jetsetter | @lindseytravels |

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Spa at Kimpton Seafire Hotel
Pool at Kimpton Seafire Hotel
Exterior of a bungalow at Kimpton Seafire Hotel

Kimpton Seafire Resort + Spa

From the moment you set your sandaled foot inside this Kimpton’s cinematic lobby—a stunning expanse of 20-foot ceilings and black iron accents—it’s evident that this Kimpton is no ordinary Caribbean escape. In lieu of a typical tropical aesthetic, this Seven Mile Beach boutique delivers a more contemporary interpretation of the Cayman Islands. Think tribal prints, coral stone, and mod furniture in guest rooms. The vibe, too, is fresh and fun. The library features prints by local artist Dready along with a wooden Cayman catboat centerpiece, while Avecita, a restaurant-within-a-restaurant, gives diners a glimpse at tapas making. If all else fails, set up shop on one of the vermillion poolside lounge chairs, summon up a rum cocktail, and take in a technicolor sunset.

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Stringrays bypass this diver in search of the next diver with food. Grand Cayman.

Stingray City

One of Cayman’s quintessential experiences is paying a visit to Stingray City, a collection of shallow sandbars in Grand Cayman’s North Sound home to a surprising number of—you guessed it—stingrays. It may be touristy, but there’s arguably no place easier (or more beautiful) to get up close and personal with these beautiful marine creatures. Five Star Charters gets you there in style, and has snorkeling gear, snacks, and drinks, and even a jet ski on board for excursions to Starfish Point (where you can see and hold live starfish) if you’d like to extend your afternoon of fun.

The Lobster Pot

Show up early if you want to score a seat on the overwater deck at The Lobster Pot, a family-owned hangout opened in 1965 that’s still one of the island’s most popular restaurants. Lobster, served Cayman-style (cut into chunks and sautéed in spicy sauce with fried plantains and rice) is the thing to get, along with the fluffy coconut pit—so save room for dessert.


Willing to venture away from the water for a moment? Camana Bay, a new open-air development of sorts that’s fast becoming the place to live and hang on the island, is full of sleek new restaurants worthy of a taste. Abacus is one of the best—a farm-to-table restaurant with a charming shaded patio, a stellar drink menu (many of its cocktails incorporate seasonal local fruits), and dishes that spotlight local purveyors. Not sure where to start? The sashimi of the day is always a hit.

Beach horse-riding in summertime

Barkers Beach

Horseback riding on the beach is one of those pinch-me moments every animal lover should experience, and one of the best spots to do it is Barkers Beach. Part of Barkers National Park in West Bay, it’s lined with dense mangroves and remains a beloved, uncrowded spot for taking a dip. Book a tour with Pampered Ponies and you’ll be able to take one of their horses out onto its untouched shores at the time of your choosing, be it early morning, at sunset, or under the moonlight. For an added experience, they’ll even de-saddle your horse so you can ride them bareback right into the sea. (Don’t worry—they love it!)

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Cayman Craft Market

You’ll find your fair share of luxury boutiques in Georgetown, Grand Cayman’s capital city, but for a truly authentic souvenir, the only place to shop is downtown at the Cayman Craft Market. This is where local artists and artisans sell their indigenous handicrafts—everything from jellies and pickles to jewelry, clothing, and décor crafted from local wood, shell, and thatch palm (the national tree) as well as recycled material like paper and soda cans. A particularly unique find to look out for: Caymanite, a semi-precious, earth-toned rock found only in the Cayman Islands.

Kaibo Beach Restaurant

What better way to end the day on a high note than with dinner and drinks at Kaibo? At this breezy open-air setup on the beach, the drinks are as delicious as the grub, and the views overlooking North Sound and the sunset are unbeatable. The seafood options here are as fresh as it gets; we’d suggest starting with the grouper dip, conch fritters (an island speciality), and a mojito mixed with rum from their Rare Rum Cabinet, then getting into the island spirit during an impromptu volleyball tournament or dancing to the spinning DJ.

What to Wear When You’re There

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