The Best of the Cayman Islands: 16 Ways to Go Big Before Going Home
Updated: Oct. 23, 2018
The Cayman Islands may tick all of the boxes you’d expect of a Caribbean getaway, but there’s more to this swanky sun destination than sandy beaches, crystal-clear waters and classic rum cocktails. Here’s our ultimate guide to the very best its three distinctly-flavoured islands have to offer.
Why Choose the Cayman Islands?
Let’s get one thing clear right off the bat: the Cayman Islands are not your generic “sun destination.” Sure, they tick off the major boxes you’d expect of a Caribbean getaway—stunning sandy beaches, crystal-clear waters and an endless menu of rum-based cocktails—but that’s where the similarities end. You’ll be hard-pressed, for instance, to find an all-inclusive resort on the whole of Grand Cayman, let alone its two smaller Sister Islands, Cayman Brac and Little Cayman. What makes Cayman unique is that instead of catering to budgets, it caters to bon viveurs—the type of traveller who wants to “go big” before going home. It’s a place where locally-grown, meticulously-prepared food trumps the all-you-can-eat buffet, and where the lure of new adventures and experiences makes lounging by the pool feel like a waste of time. It won’t come cheap (at the moment, the Cayman Islands is the second most expensive destination in the Caribbean), but the richness of the experience makes it worth every Caymanian dollar.
Here’s how to max out your Cayman Islands adventure, and sample the very best these three distinctly-flavoured islands have to offer.
Travel tip: Don’t want to sound like a tourist? Never refer to the islands as “The Caymans.” It’s either “the Cayman Islands” or “Cayman.” Likewise, locals refer to the largest of the Cayman Islands (and the one you’ll likely be flying into) as “Grand Cayman” instead of “Grand Cayman Island.”
The Best Place to Swim With the Stars
Starfish Point, Grand Cayman
It’s not just sun-worshippers who are drawn to this breathtakingly beautiful beach on the tranquil eastern rim of Grand Cayman’s North Sound. The warm, crystal-clear waters just off the shore play host to hordes of colourful starfish that trawl the shallows in search of food. These fascinating five-legged creatures don’t seem to mind sharing their habitat with curious beachcombers, so long as they’re left under the water’s surface—exposed to air, they can suffer tissue damage within seconds.
Travel tip: Planning on Instagramming your close encounters of the aquatic kind? It’s best to purchase an international data package with your Canadian carrier before you leave home. Roaming charges in the Cayman Islands can set you back as much as $300 a day!
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The Best Place to Order a Mudslide
Rum Point, Grand Cayman
After spending the afternoon on Starfish Point’s spectacularly secluded beach, head next door to Rum Point—the closest to a real-life “Margaritaville” you’re likely to find in the Caribbean, let alone Grand Cayman. Here, the islands’ torrid history of swashbuckling and smuggling comes to life in a colourful cluster of pirate-themed bars and burger joints. Grab a seat at one of the brightly-painted beachfront picnic tables and soak up the sun while sipping the local speciality—the (oddly rum-less) Mudslide. Served on the rocks, the creamy concoction of vodka, Kahlua and Irish cream is rumoured to have originated here in the 1950s, and remains a truly decadent treat that goes down (dangerously) easy.
Travel tip: You can actually order a mudslide from the very bar that claims to have invented the cocktail more than 60 years ago. It’s worth checking out Rum Point’s Wreck Bar if only to set the benchmark by which all other mudslides should be judged.
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The Best Place to Eat Local
The Brasserie, Grand Cayman
There is no shortage of superb dining options in the Cayman Islands, which has justly earned its reputation as “the Culinary Capital of the Caribbean.” Unusually for an island nation, it’s also extremely easy to eat local, with a number of the country’s most highly-regarded chefs embracing a farm-to-table approach with their cuisine. One of the finest examples you’ll find on Grand Cayman is The Brasserie, where Chef Dean Max incorporates herbs and vegetables grown in the on-site kitchen garden in his sensational fresh-caught seafood creations.
Travel tip: Sucker for ceviche? You can’t choose a better spot in George Town. A mouthwatering mix of spicy coconut milk, sweet potato, mint and cilantro, the Brasserie’s red snapper ceviche is one of the most in-demand items on the menu.
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The Best Place to See (and Be Seen)
Seven Mile Beach, Grand Cayman
Seven Mile Beach is actually only 6.3-miles long, but given the fact this crescent-shaped stretch of sun-kissed shoreline is arguably one of the world’s best beaches, it’s easy to forgive the slight exaggeration. Although this is where Grand Cayman’s greatest resorts are clustered—and most of its tourists, for that matter—the beach that the resorts back onto remains public property, which means you can walk its full length no matter where you’re staying. What’s even more unusual for a major Caribbean beach, you can do so without being hassled by vendors selling tacky trinkets—it’s forbidden by law.
Travel tip: If you can, schedule your visit to Seven Mile Beach in mid-January when it plays host to the legendary Cayman Cookout. Hosted by world-renowned chefs (we’re talking Anthony Bourdain and Eric Ripert, among others), this five-day festival of Caribbean cuisine and cocktails is an essential experience for any foodie.
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The Best Place to Tie the Knot
Ritz-Carlton, Grand Cayman
Destination weddings remain a popular option for Canadian couples, and Cayman is catering to the demand with characteristic flair. In fact, in 2017, its Department of Tourism launched a glossy new magazine—Cayman Vows—devoted entirely to would-be brides, grooms and wedding planners considering tying the knot in this tropical paradise. Although virtually every major resort on Seven Mile Beach is equipped to serve as a stunning wedding venue, the Ritz-Carlton is particularly renowned for pulling out all the stops. Whether you’re looking for a pretty, pared-back beachside ceremony, or a stately soiree on the hotel’s verdant, palm-lined Great Lawn (complete with wedding pavilion), it’s bound to be an elegant affair in the hands of the resort’s accomplished wedding advisers.
Travel tip: Consider scheduling your Cayman Islands wedding in summer or fall, which are generally considered off-season. Travelling during these times can often save you as much as 30 per cent. Check the Cayman Islands website for current off-season promotions.
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The Best Place to Go Underground
Crystal Caves, Old Man Bay, Grand Cayman
Whether you’re an intrepid explorer, or simply looking for a way to beat the Caribbean heat, Crystal Caves are sure to satisfy. Formed over millions of years, the “oldest natural wonder” on Grand Cayman offers spectacular spelunking opportunities through three caverns filled with fascinating rock formations, including the eponymous “crystals”—calcium-based stalagmites and stalactites that seem to shimmer in the half-light. Whether or not you buy the story that the caves still contain buried treasure from the pirates of Cayman’s past, there’s no denying their natural beauty, and the sense of wonder they inspire in visitors young and old.
Travel tip: When you go, trade the flip flops for sneakers—the uneven terrain in the caves can be treacherous in open-toed shoes.
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The Best Way to Get There
Air Canada, Toronto to George Town (direct)
When you’re in desperate need for vitamin D, the last thing you want to do is waste precious time waiting for your connection at the Miami airport. The good news? Effective Dec. 15, 2017, Air Canada expanded its Toronto to George Town service with six non-stop flights per week through early April. In real terms, these direct flights into the Cayman Islands’ capital will have you trading your snowsuit for swim trunks in a scant four hours.
Travel tip: Synchronize your watches! Although the Cayman Islands are on Eastern Time, they do not observe Daylight Saving Time.
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The Best Place to Jet Ski
Red Sail Watersports, Grand Cayman
If you find it stressful driving on the left-hand side (which, along with the abundant roundabouts, are a lasting legacy of British colonial rule), taking to the waves could prove the perfect tonic. There’s something incredibly exhilarating in tearing across the Caribbean Sea on a jet-ski, unshackled by the rules or the road, and a half-hour rental from Red Sail Watersports is the best way to satisfy that need for speed. Never been on a jet-ski before? No problem! The calm waters off Seven Mile Beach are the ideal training ground for novices, and after a brief tutorial from Red Sail’s friendly staff, you’ll be riding the waves with confidence.
Travel tip: Caymanians often refer to jet skis as “wave runners.”
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The Best Place to Stay
Kimpton Seafire, Grand Cayman
There might be others that are larger or more opulent, but there’s arguably no resort in the Caribbean as downright chic as the Kimpton Seafire. The first new hotel to be built on Grand Cayman in a decade, the Seafire positively oozes au courant elegance, from its gleaming polished stone and weathered wood bones down to the tiniest tabletop accessory. What’s more, there’s been a conscious effort to integrate a distinctly Caymanian flavour into the sophisticated decor, with rope, shell, driftwood and locally-produced artwork—not to mention the floor-to-ceiling windows throughout—grounding the luxurious digs with a real sense of location. Aesthetics aside, this “lifestyle resort” boasts some of the best amenities in the Cayman Islands, including a prime location on Seven Mile Beach, fitness classes that range from pool-based aquafit to paddleboard yoga, and no fewer than three superb restaurants.
Travel tip: Although each of the gorgeously-appointed guest rooms comes with balcony, splurge on an ocean-facing suite, which affords spectacular views of the fiery sunsets that earned the hotel its name.
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The Best Place to Recover From an Afternoon in the Sun
Spa at Seafire, Kimpton Seafire, Grand Cayman
Take an impossibly comfy lounge chair on Seven Mile Beach, throw in the friendly—and dangerously attentive—drinks service from the staff at the Kimpton Seafire’s Coccoloba beach bar, and you’ve got the perfect recipe for a sunburn. On the upside, the fix for that rosy-red hue is just a few steps away at the resort’s 8,500-square foot Spa at Seafire. Here, you can turn back the clock with the popular Sun Rewind facial, which uses natural ingredients like aloe vera, green tea and sea minerals to hydrate and nourish sun-damaged skin. By the end of the 60-minute treatment, you’ll be looking more sun-kissed than scarlet, and fresh-faced for an elegant dinner.
Travel tip: Build in a buffer between your spa treatment and dinner reservations so you can make use of the spa’s gorgeous steam room.
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The Best Place to Spot Endangered Species
Queen Elizabeth II Botanic Park, Grand Cayman
Between its brilliant aqua-coloured scales, massive size (it can grow five feet long) and face only a mother could love, the Cayman Blue Iguana is about as close as it gets to a real-life dragon. It’s nearly as rare as its fictional counterpart, too, at one point numbering just three in existence. Thanks to the conservation efforts of the folks at the Blue Iguana Recovery Program, the critically endangered species—which is only found on Grand Cayman—is bouncing back, with a current population sitting around 750. Although their numbers are still shy of the program’s goal of a full thousand, the modern-day dinosaurs can occasionally be spotted basking in the sun at the Queen Elizabeth II Botanic Park. Your best bet is to take a stroll along the park’s Wilderness Trail, where the iguanas enjoy a designated habitat amidst some of the prettiest landscaping on the island.
Travel tip: If you visit the Cayman Islands in late February, be sure to check out the Annual Orchid Show at the Queen Elizabeth II Botanic Park. Hosted in partnership with the Cayman Islands Orchid Society, the event is a must for avid greenthumbs and aficionados of exotic flora.
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The Best Way to Island Hop
Twin otter plane, Cayman Airways
Glitzy Grand Cayman has a habit of stealing the spotlight, but the Sister Islands of Cayman Brac and Little Cayman have their own charms, particularly for travellers who prefer an “off-the-beaten-path” experience. What’s more, getting there is half the fun, as you’ll likely be hopping on board one of Cayman Airways’ teeny-tiny twin otter planes for the quick—and quaint—puddle jump. From the open-air cockpit (aviation geeks will love the opportunity to watch pilots at work!) to the cozy bench seating, it’s an utterly delightful experience, and perfectly in-line with the laid-back vibe of the Sister Islands.
Travel tip: Although the airport terminals on the Sister Islands are little more than cottages, typical airport security measures are still in place. You’ll need to present your passport, and standard aviation policies restricting the transportation of liquids and other goods apply.
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The Best Place to Get Away from it All
Little Cayman Beach Resort, Little Cayman
If you’ve ever dreamt of a desert island holiday, you’ll find the aptly-named island of Little Cayman ticks all of the boxes. Largely uninhabited, it’s estimated the island’s iguanas outnumber the permanents residents 10 to one. Throw in endless stretches of pristine beach, unspoiled mangrove forests and a perfectly charming place to rest your head in the form of the Little Cayman Beach Resort, and you’ve got yourself the perfect side-trip from the hustle and bustle of Grand Cayman. While you’re there, be sure to book yourself a table for dinner at the Hungry Iguana—the island’s sole restaurant. Specializing in Cajun cuisine (and home to a number of incredibly friendly house cats), the true highlight of the humble establishment is its self-serve bar which operates on the honour system: Simply grab yourself a drink from the fridge, and record it in the log. Now that’s island hospitality!
Travel tip: Typical resort wear is far too formal for both Little Cayman and Cayman Brac. The relaxed vibe of the Sister Islands calls for casual attire—think tank tops and flip-flops. (Here’s our Ultimate Guide to Dressing Appropriately for Every Occasion!)
The Best Place to Admire Local Art
The National Gallery of the Cayman Islands, Grand Cayman
The spectacular natural beauty of Cayman has fuelled the creativity of countless generations of artists—many of whom are represented at the stunning National Gallery of the Cayman Islands. Here, preserved on canvas and in ceramic, is the story of the Cayman Islands, offering invaluable insight into the lives of its people and the land they share with approximately 2-million visitors each year. Among the true standouts of the collection are the works of Shane “Dready” Aquart (above), whose bold, graphic prints depicting quintessentially Cayman activities (think sailing and snorkelling) against brilliantly-coloured backdrops make eminently stylish souvenirs.
Travel tip: You don’t have to visit the Cayman Islands to snag yourself a coveted Dready. Check out the artist’s online shop, where you’ll find his eye-catching, contemporary prints adorning everything from t-shirts to bookmarks. (Here are tips on How to Start a Home Art Collection—Without Breaking the Bank!)
The Best Place to Indulge in Some Retail Therapy
The Shops at Camana Bay, Grand Cayman
Whether you’re looking for a chic souvenir, sunglasses to replace the ones you forgot to pack or a shamelessly frothy beach read, you’ll find it at the ritzy Shops at Camana Bay. This master-planned mixed-use community in George Town spans a whopping 650-acres, boasting dozens of retail shops and restaurants, as well as a six-screen movie theatre and weekly farmers’ market. Worthy of at least one of your evenings on Grand Cayman, we recommend starting the night at the West Indies Wine Company. Whether or not you partake in a proper wine tasting, you absolutely must experience wine by-the-glass from the shop’s wondrous self-serve wine-dispenser—an essential experience for any budding oenophile.
Travel tip: Be sure to get your fill of retail therapy Monday through Saturday: there’s virtually no Sunday shopping in the Cayman Islands.
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The Best Place to Watch the Sunset
The Observation Tower at the Shops at Camana Bay, Grand Cayman
If you didn’t snag an ocean-view room at the Kimpton Seafire, you can still catch the legendary Grand Cayman sunset from a prime vantage point. Rising 75-feet over George Town, the Top Deck of the Observation Tower at the Shops at Camana Bay offers panoramic views of the city from sea to sound, and equally impressive architecture within. The tower’s how-did-they-do-it double-helix staircase, lined with a magnificent mosaic composed of more than 3-million Venetian glass tiles, makes the walk up several hundred steps well worth your while.
Travel tip: Rather not sweat the stairs? Take the elevator straight to the top! (Here are more epic elevator rides from around the world!)
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