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Cayman Islands Travel Guide

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The Cayman Islands may be a banking center, but business travelers stay for diving and the sun.

With long white-sand beaches as bleached out as powdered sugar, bright green palm trees and pale blue water, the Cayman Islands look just like the screen-saver image you’ve been hoping to jump into. Fortunately, they also have great luxury hotels, fabulous celeb-chef restaurants and some of the region’s best scuba dives, as well as the area’s newest.

Best of all, with plenty of nonstop flights from the U.S., you can get there quickly and maximize your time on the shore. So, if you’re planning to come for business—as many people do in this center of offshore banking, which is second only to Switzerland—there’s no reason not to stay for pleasure. With the sand and surf waiting outside your conference room window, by the time your work is finished you’ll be ready to play, or at least spend the rest of the day sunning and sipping umbrella-topped drinks.

Where to Stay

Ritz-Carlton Grand Cayman: Often called one of the best resorts in the Caribbean, this gorgeous property on Seven Mile Beach (the island’s longest strand) racks up the accolades for good reason. Room decor is colonial-inspired, with carved four-poster beds and heavy drapes, but the Silver Rain spa (run by Swiss dynamo La Prairie) is as sleek and modern as can be. Unlike many resort spas, there’s nothing clinical or cold about this space, including gorgeous chandeliers you’ll wish you could take home, plush white rugs, and a cool gray and silver color scheme. Get a decadent massage—or a La Prairie facial, or a body scrub using local sea salt—in one of the mosaic-tiled treatment rooms. Then, head back out to the beach, where the resort sets up floating furniture in the surf.

Cotton Tree: The island’s first boutique hotel is made up of four candy-colored two-bedroom cottages that are stylish and spacious. While the rooms are comfortable, even chic, what’s most surprising is the way that this thoughtful hotel takes care of some of the details that drive business travelers nuts elsewhere. There’s no nickel-and-diming here, for example, as both airport transfers and Wi-Fi are included. The guestrooms have kitchens, and you can hire a personal chef to make you whatever it is you like to eat when you get tired of the resort restaurants.

Compass Point: Made up of 28 one-, two-, and three-bedroom condos, this relaxed new dive resort is a great choice for those who want to bring the friends or family down to strap on some tanks. Located on Grand Cayman’s quieter East End, the unfussy rooms have balconies and kitchens, and there are shared barbecue pits on the deck, so you won’t be forced to live on overpriced room service, at least for this part of your trip. This is a great choice for active travelers looking for rugged, independent exploration rather than cocktails in a cabana: You can borrow the resort’s kayaks and bicycles, and dive boats go out twice a day.

Where to Eat

Michael’s Genuine Food and Drink: This celebrated Miami restaurant opened a Cayman Islands outpost last June, and it serves as local a menu as the Florida branch. Seafood is a focus of many of the best dishes here. Start with a small plate of locally caught snapper, served ceviche-style and topped with locally grown mango, or the locally caught blackfin tuna, which is presented as a crudo with preserved Meyer lemon and local fennel. Follow that with a pan-roasted local snapper topped with plantains that are (you guessed it) grown locally. Whatever you do, save room for dessert: When the options are a lemon pot de crème served with house-made cannoli and sticky toffee pudding with house-made mango ice cream, you’ll be glad you can fall back on the age-old holiday rule of trying them all.

Blue at the Ritz-Carlton: It’s a gift to find a chef of Eric Ripert’s caliber in the Caribbean, and while he follows in the footsteps of Nobu Matsuhisa and Bobby Flay, who opened outposts in the Bahamas first, it’s still a wonderful treat to dine on food of this quality after a day at the shore. Wash the sand out of your hair, dress up (if only a little) and prepare to be wowed. You won’t forget where you are, even if you don’t dine on the terrace: The menu is a celebration of responsibly fished local seafood, from a trio of conch to hamachi sashimi, wahoo tartar and gently poached halibut.

Osetra Bay: Arguably the most sophisticated spot on this otherwise casual Caribbean island, Osetra Bay is designed to look like a series of increasingly fabulous urban lounges. The caviar theme extends to the cocktail menu: Settle into the Gold or Silver Lounge, and order caviar served up with either Champagne or the house specialty, Gold Cuvée, a white wine laced with 22-karat gold flakes. Stay for dinner, and you can continue the theme of extravagance with foie gras and butter-poached lobster. If you decide to charter a yacht while you’re in town, the restaurant has a dock that you can sail right up to.

Calypso Grill: Looking for something more, um, local? Calypso Grill, located next door to Osetra Bay, is the place to be for simple grilled fish, crab cakes, rum punch and sticky toffee pudding, all served dockside. The alfresco restaurant is casual and come-as-you-are—but you’ll still need to make reservations way in advance if you want to dine here over the holidays.

What to Do

Seven Fathoms Rum Tour: No product is as associated with the Caribbean—or as ideal as a souvenir—as locally made rum. Many islands have their own brands, and on the Cayman Islands, the local choice is Seven Fathoms, the first rum-maker to age its product underwater in oak barrels. You can order punch made with the hometown favorite at bars all over the island, or visit the distillery for a walk through the process of rum-making and maturation, followed by a tasting.

Snorkeling Stingray City: This 12-foot dive is the most popular spot for undersea fish–viewing, which is a big statement for an island with a dive site for every day of the year. Even if you don’t dive, you should make the pilgrimage, since there’s a sandbar just three feet below the surface that will help you snorkel around the rays. The Ritz-Carlton’s best advice: Go on a Saturday during high season (when there are few cruise ships in port) or any afternoon, because by 4 p.m. the ship passengers will be on their way back to the dock and you could have this often crowded spot to yourself.

Diving Kittiwake: Last January, the shipwrecked submarine rescue ship Kittiwake was sunk in a private marine park on the northern end of Seven Mile Beach as a 251-foot-long steel home for sea life. It quickly became habitation for a 100-pound goliath grouper, massive barracuda, and schools of horse-eye jacks and Caribbean reef fish, as well as divers seeking to get a look at the area’s newest reef. Those who don’t dive can snorkel over the top of the ship, across the main decks and past the smokestack, whose funnel provides a bird’s-eye view into what was once the engine room.

Sherri Eisenberg is a travel and food writer who always has her bags packed and ready to go.


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