On the still-bucolic site of a former coconut plantation just west of Montego Bay, Round Hill is another of the legendary hotels created in the early 1950s to accommodate wealthy Brits and Americans who were discovering the pleasures of a Jamaican winter. Since then, it has evolved into a thoroughly modern resort that manages to retain its original, exclusive, clublike spirit. In the beginning, Round Hill consisted of a group of shareholders (British playwright Noel Coward was one) who rented out their private villas when they were absent. That’s how it still works, although the celebrity shareholder most mentioned these days is designer Ralph Lauren, who rents neither of his two villas. Along with 27 other villas, which can be divided into 86 suites, there’s the Pineapple House, a seafront block of 36 rooms, all decorated, predominantly white on white, by Lauren. The ambience is quiet luxury, the service is relatively formal (the doorman wears white), and the children among the guests are treated as the heirs and future holiday decision makers that they are. Almost every villa has a story, whether it has to do with Coward, the Kennedys, or How Stella Got Her Groove Back. And Montego Bay, whose city lights can be seen only from the highest villa (#28), is still another world away.
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About 20 minutes west of the airport at Montego Bay, Round Hill is relatively isolated. For golfers, though, Tryall, one of the island’s top courses, is only a few miles away. Round Hill will make reservations and provide a free shuttle. Round Hill’s beach is smallish, and although it offers all the usual water sports, true beach lovers will want to organize an outing to Negril’s Seven-Mile Beach, 40 minutes away. The vendors can be relentless, but the texture of the sand and the color of the water make the trip worth it. While there, head a little farther out of town to the Rockhouse Restaurant, which, from its perch atop a sea cliff, serves up contemporary Jamaican fare and the best sunsets on the island. For time in the saddle, head east, just outside of Montego Bay, to the Half Moon Equestrian Center, which offers everything from pony rides to beach rides to—of particular interest for the landed gentry among Round Hill’s guests—polo instruction.
Need to Know
Rooms: 36 rooms, and 27 villas with 86 suites. From $399 low season, $689 high season. Check-in: 3 p.m.; check-out: noon. Dining options: In the Seaside Terrace for dinner or the Grill at Round Hill for breakfast and lunch, James Beard award–winning chef Martin Maginley creates a Jamaican-flavored menu to please the palate of even visitors who did not grow up on oxtail and Scotch bonnet. Afternoon tea in the Cocktail Bar is well-attended, and most popular among theme dinners is the barefoot beach BBQ, perhaps because it is the only evening meal at which shorts are not prohibited. Spa and gym details: The Spa at Round Hill is the oldest beachfront spa in Jamaica, but more relevant is its serenity-producing setting in a restored 18th-century great house. Along with eight treatment rooms offering a full menu of services, it also has a small fitness pavilion and an adults-only pool.
Who’s it for: Scions, celebrities, and their offspring. Our favorite rooms: The 36 rooms in the Pineapple House are closest to the water and the infinity pool, with the best views from the second floor. For space and quiet, though, opt for one of the villas, which are hard not to choose for their history. JFK and Jackie preferred Villa 10 (although he practiced his inaugural address on the pool deck of Villa 25). Villa 11 was the setting for the film How Stella Got Her Groove Back. And Oscar Hammerstein penned more than one of his musicals in Villa 12. Villa 16, though, is the most spectacular, especially for guests needing two private pools and six really big bedrooms. Little-known fact: Guests who are feeling visionary might like to know that Jamaican socialite and serial entrepreneur John Pringle, who came up with the ownership scheme for Round Hill when he was 26, was a cousin to Island Records and Island Outpost founder Chris Blackwell. Coincidence or commercial blood?