Let’s say you’re fashion designer Ralph Lauren, and you’re looking to take a much-needed vacation. Obviously, the world is your oyster; you can fly to essentially any corner of the globe and be embraced with open arms. But you, Ralph Lauren, do not go just anywhere. You choose the same place for many of your hard-earned holidays with your family, and you choose it repeatedly, multiple times each year. Welcome to Round Hill Hotel and Villas, on one-hundred-and-ten lush areas in Montego Bay, Jamaica.

Built in 1953, Round Hill was the resort of choice for old Hollywood. Everybody from JFK and Jackie—who spent part of their honeymoon there—to Grace Kelly, Paul Newman, Clark Gable and Babe Paley have stayed in its private villas. These villas are ironically known in Round Hill parlance as “cottages” – although they’re far from quaint. In recent years, guests have included Ryan Gosling, Paul McCartney, Lupita N’yongo, Idina Menzel, Heidi Klum, and Michelle Williams.

The draw for celebrities at Round Hill is obvious—privacy and tradition abound. It’s the sort of place where you can shower al-fresco underneath leafy palm fronds or enjoy a dip in your own pool overlooking the clear turquoise waters–with nobody else in sight. Each day, at precisely 4 p.m., tea, sandwiches and cocktails are served under the old-fashioned bar’s striped awnings, while each week guests congregate on the white sand for a formal beach barbecue to the strains of live music. There’s the yearly black-tie Sugar Cane Ball—one of the premiere charity events in the Caribbean—as well as Christmas and New Year’s Eve celebrations. The concierge Kingsley has been there for more than 40 years, and most of the staff has grown up together or is related to each other, giving the whole place a cozy, familial atmosphere.

Of the twenty-seven Cottages on property, Ralph Lauren owns two—part of a unique agreement allowing would-be owners at Round Hill to purchase a villa and rent it out for part of the year to guests. The Cottages range from cute one bedroom half-villa suites to sprawling 8,000 square-foot, six-bedroom complexes with two pools and epic Caribbean views. All villas, meanwhile, have a personal staff of three: your very own chef, housekeeper and gardener. While most owners rent out their villas to guests year round, Lauren chooses not to. His homes, the High Rock and the White Orchid are private–but the trade off is worth it for the other guests, who buzz about spotting him by the ocean-front pool during his regular visits in the winter and early spring.

While part of Round Hill’s magic is to be found in its private and semi-private Cottages, when those are full—usually during high season, running from December to February—there’s still the charming main hotel. Called Pineapple House, the hotel features thirty-six oceanfront guestrooms with four-poster mahogany beds plus louvered windows for maximum views or private walkout patios. And, like most of the resort’s common areas, all rooms are designed and outfitted in Ralph Lauren Home, naturally.

It’s not hard to understand why families like the Laurens (and the McCartneys and the Douglases and countless other society mainstays) have returned year after year. Fresh coconuts under the baking sun; the aroma of salty sea breeze swirling over the resort’s namesake sloping hill; the steamy nights; the incredible hospitality.

Of course, it helps that every last inch of the place feels art-directed from the world’s most glamorous photo shoot. But despite all the glitz and glam, Round Hill is a surprisingly down-to-earth, intimate retreat. Guests mingle on the beachfront patio over tea and rum punches, flit from table to table during al-fresco dinners and chat freely while lounging by the infinity pool overlooking the sea. It’s a family place, begging repeat visits. It’s no wonder Ralph Lauren and Co. have been swept under its spell.

From: Harper’s BAZAAR US

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