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THE CAYMAN ISLANDS form a picture-perfect vacation destination, a small but mighty one that’s long on stunning vistas and truly has something for everyone. The 102-square-mile archipelago — comprising Grand Cayman, Cayman Brac, and Little Cayman — has a local culture and food scene considered to be a unique hodgepodge of Jamaican, Afro-Caribbean, and British customs. Known for their pristine beaches and tax-free status, the Cayman Islands have been a premiere destination for cruise-ship passengers who make the stop for aquatic excursions and luxe duty-free shopping. The islands’ cultural calendar is filled with annual festivals, such as the Cayman Cookout Festival, helmed by Chef Eric Ripert and hosted at the Ritz-Carlton every January, and Batabano, a local Caribbean carnival celebration which takes place in May. There’s even a Pirates Week festival every November that makes a tour of each island. Activities include invasion reenactments, costume competitions, and boat races.
Against that fun-in-the-sun backdrop, there also seems to be an exciting resurgence of cultural curiosity and reimagining taking place on the islands. An emerging local arts scene is driven by the National Gallery of the Cayman Islands, which, along with a permanent collection, exhibits work from contemporary Caymanian artists. In 2022, the Cayman LGBTQ Foundation hosted its second-ever Pride Parade. Palm Heights — Grand Cayman’s first boutique resort, which opened in 2020 along Seven Mile Beach — joined in on the festivities, curating a week of activities and drag cabarets with a cast of global artists and creatives. In addition to being a thoughtfully designed space, Palm Heights also hosts a robust calendar of live performances at their Supper Club, and is home to an artist residency program that attracts musicians, designers, and artisans from Cayman and abroad. Though all of the islands offer something unique, for many visitors, Grand Cayman is the main event — here’s a list of where to go and what to do when there.
Where to Eat and Drink
The dining scene is going through a revival of sorts with farm-to-table menus and trendy natural wine cropping up all over the island of Grand Cayman. The island’s offerings range from fine-dining fare to poolside snacks, but regardless of where your tastes lead you, a meal is best washed down with a local Caybrew lager.Tillies
Fresh seafood meets fashionable decor
As the crown jewel of Palm Heights' culinary experiences, Tillies holds its own as a fine-dining establishment that feels at once fancy and cozy. The service is all white linen, but the maximalist decor and leopard-print carpet feel exquisitely lived in. The rotation of menus and experiences...
As the crown jewel of Palm Heights' culinary experiences, Tillies holds its own as a fine-dining establishment that feels at once fancy and cozy. The service is all white linen, but the maximalist decor and leopard-print carpet feel exquisitely lived in. The rotation of menus and experiences ranges from the freshest seafood towers to a hearty Sunday roast and High Tea service replete with cucumber sandwiches, scones, and clotted cream. Executive Chef Jake Tyler Brodsky and his team hit the mark flawlessly with each tasty iteration.
Ms. Piper's Kitchen + Garden
Cozy fusion food in a garden setting
Evoking free-spirits and effortless feminine energy, the aura at Ms. Piper’s Kitchen + Garden is inspired by a fictional yet chic elderly hostess rumored to have decamped to Grand Cayman in the 1970s. Tucked away in a lush garden right off Seven Mile Beach, the cottage-style restaurant offers a...
Evoking free-spirits and effortless feminine energy, the aura at Ms. Piper’s Kitchen + Garden is inspired by a fictional yet chic elderly hostess rumored to have decamped to Grand Cayman in the 1970s. Tucked away in a lush garden right off Seven Mile Beach, the cottage-style restaurant offers a menu of fusion-oriented fare that includes cassava cheese bread, Korean glazed ribs, and mezze platters. Their custom cocktails are named after famous and infamous women such as the Yoko Ono (an effervescent mix of vodka, grapefruit, and kombucha) and the Celia Cruz (Havana rum, smoked berries, and lemon meringue foam).
Mambo Italiano Karaoke Night at Paradise Pizza
Italian eats and bumping beats in an open-air restaurant
It’s no coincidence that one of our top picks for lodging has also made the cut for dining and entertainment. The team behind Palm Heights has curated a roster of events that brings top-notch musicians and DJs right to your cabana. And every Saturday night the real fun happens when they turn the...
It’s no coincidence that one of our top picks for lodging has also made the cut for dining and entertainment. The team behind Palm Heights has curated a roster of events that brings top-notch musicians and DJs right to your cabana. And every Saturday night the real fun happens when they turn the mic over to the guests at Paradise Pizza’s Mambo Italiano Karaoke Night. Be prepared to belt out your tried-and-true karaoke favorites over a menu of Neapolitan pizza and Roman pasta. And if it’s a really jumping night, don’t be surprised if the head chef does his rendition of Frank Sinatra’s “My Way” between courses.
Where to Explore and Shop
Whether you’re looking to deep dive into nature or to splurge on an exceptional object, the Cayman Islands offer the best of both worlds. Since the islands have a no direct taxation policy — meaning, sales are duty-free — big-ticket purchases are quite inviting. Just don’t forget to take in the arts in between shopping and snorkeling.National Gallery of the Cayman Islands
A hub of culture and contemporary art
With a mission to “promote the appreciation and practice of the visual arts” on the islands, the National Gallery of the Cayman Islands has become a hub for cultural activity, education, and even a bit of wellness. Founded in 1996, the museum is focused on positioning Caymanian art at the...
With a mission to “promote the appreciation and practice of the visual arts” on the islands, the National Gallery of the Cayman Islands has become a hub for cultural activity, education, and even a bit of wellness. Founded in 1996, the museum is focused on positioning Caymanian art at the forefront. The permanent collection spans from traditional crafts pieces to modern and pop art developed by local artists. Events include a biennial auction and costume gala in the fall, as well a springtime tea party.
Camana Bay
One-stop outdoor shopping destination
Camana Bay is a one-stop destination for shopping, dining, and entertainment. The outdoor center features a network of boutiques, restaurants, fitness studios, and a cinema along a scenic harbor. The weekly Farmers & Artisans Market is a must for the island’s freshest produce and craft goods.
Crystal Caves
Stunning natural wonders off the beaten path
Be sure to plan ahead for your trip to the Crystal Caves of Grand Cayman. About 50 minutes from the main strip of Seven Mile Beach, this trio of stalactite and stalagmite crystal structures — including the open-ceiling cave, the roots cave, and the lake cave — makes for an ideal day trip. Guided...
Be sure to plan ahead for your trip to the Crystal Caves of Grand Cayman. About 50 minutes from the main strip of Seven Mile Beach, this trio of stalactite and stalagmite crystal structures — including the open-ceiling cave, the roots cave, and the lake cave — makes for an ideal day trip. Guided tours require prebooking and include a 30-minute nature walk in the surrounding tropical forest.
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Where to Stay
Regardless of your group size or your preference for where to rest your head, the Cayman Islands have something for everyone. Thankfully, accommodations run the gamut from indulgent all-inclusive properties to far-flung quaint hideaways tucked along rocky coastlines.Le Soleil d’Or
Rustic-chic guest house off the main island
For those seeking slightly more secluded accommodations, hop over to Cayman Brac — the smaller island 90 miles northeast of Grand Cayman — and stay at Le Soleil d’Or. Le Soleil d’Or offers a constellation of private villas nestled among botanical gardens and 20 acres of rustic farmland on Cayman...
For those seeking slightly more secluded accommodations, hop over to Cayman Brac — the smaller island 90 miles northeast of Grand Cayman — and stay at Le Soleil d’Or. Le Soleil d’Or offers a constellation of private villas nestled among botanical gardens and 20 acres of rustic farmland on Cayman Brac’s southern coast. An assortment of beach houses provides lodging for groups ranging from two to four, and an on-site farm-to-table restaurant serves breakfast daily, which is included with your stay.
Palm Heights
Design and culture-forward boutique hotel with multiple restaurants
Palm Heights has made a name for itself as an ambitious and thoughtfully designed space where almost anything is possible and no inch is left unconsidered. From its decor of statement-worthy midcentury-modern design to its surprisingly daring culinary program, forthcoming outdoor spa and hammam,...
Palm Heights has made a name for itself as an ambitious and thoughtfully designed space where almost anything is possible and no inch is left unconsidered. From its decor of statement-worthy midcentury-modern design to its surprisingly daring culinary program, forthcoming outdoor spa and hammam, and roster of programming and parties, Palm Heights packs it all in in its slender plot of Seven Mile Beach. Unbeholden to tradition or outdated notions about what a resort could or should be, creative director Gabriella Khalil and her team of culinary and cultural curators have excelled in reimagining Cayman as a hub of culture and design.
The Ritz-Carlton, Grand Cayman
A sprawling luxury hotel staple
As a pioneer of luxury resorts, The Ritz-Carlton is synonymous with a legacy of gilded luxury. After an extensive renovation in 2021, the brand’s Grand Cayman outpost boasts a behemoth network of over 360 suites and rooms, six bar and restaurant spaces by the legendary chef Eric Ripert, a spa...
As a pioneer of luxury resorts, The Ritz-Carlton is synonymous with a legacy of gilded luxury. After an extensive renovation in 2021, the brand’s Grand Cayman outpost boasts a behemoth network of over 360 suites and rooms, six bar and restaurant spaces by the legendary chef Eric Ripert, a spa appointed with La Prairie skincare, and a waterpark. For the all-inclusive resort lover, this is the top of the tops.
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Deidre Dyer Writer
Deidre Dyer is a writer, editorial director, and brand consultant. Her clients include brands such as Nike, Converse, Instagram, and The RealReal. Dyer’s writing has appeared in Vogue, GARAGE, SSENSE, and Riposte magazine. She is currently an editorial and publishing manager at Netflix Queue.
