Four blue-blooded Jamaican resorts live up to their illustrious reputations. Plus, a preview of next century's classics

Raymond Patrick

Tired of characterless, cookie-cutter Caribbean islands that rely on holiday hounds for their color?Try Jamaica. It's spicy. It's quixotic. It's edgy. Of course, you don't go for the food—even by regional standards, the cooking is uninspired. But the hotels, oh, the hotels. From world-class golf resorts to a high-society hideaway, they're the island's glamorous and dignified dowager duchesses, institutions whose wrinkles are worn proudly because—as old girls—they figure they've earned them.

round hill hotel & villas
Society chronicler Slim Aarons's photograph of Mrs. William S. ("Babe") Paley at Round Hill perfectly captures the mid-century fashion idol's exquisitely attenuated, Capri-panted glamour. Forty years after the CBS chairman's wife was snapped at the resort, her perfume lingers, as if she had just left the room to change for dinner. The cocktails-and-laughter aura of another founding Round Hill habitué, Noël Coward, is also felt. His world-weariness is as much a part of the compound's fabric as the woven raffia on the stools in the bar, redecorated with brio not long ago by Ralph Lauren.

But more name-dropping later. Huddled on a 100-acre thumb-shaped promontory sloping down to the water 10 miles west of Montego Bay, Round Hill is made up of 28 two-, three-, and four-bedroom private villas—most with pools—that are hired out when their owners are not in residence. (Lauren himself has a unit, but it is not for rent.) Villas are let in their entirety or as suites, each of which has its own entrance and living area. In the interest of privacy, when units are shared, the number of suites that may be occupied is capped at two. "Skeletal staff," if you can believe it, means a housekeeper and a gardener and a breakfast cook fluent in the Round Hill tradition of banana pancakes with Jamaican rum syrup. Golf carts are the only means of locomotion.

There's also Pineapple House, operated as a conventional hotel right by the shore; it has 36 perfectly okay guest rooms on two levels. But coming to Round Hill and staying in Pineapple House is like going to a salad bar and ordering a sandwich. The villas are the thing.

My villa turned out to be owned by Louis F. "Bo" Polk Jr., the former head of MGM. All schemes to catch a glimpse of the Lauren digs were thwarted, but I'm confident the Polk cottage is stylistically the next best thing to Ralph's. Open on two sides, with nothing but grommeted sailcloth curtains between me and nature, the living room faced the Caribbean beyond lush gardens planted with jasmine and frangipani. The lulling metronomic tick-tick of the lawn sprinkler invited a nap in a caned planter's chair in the morning, and in a settee fashioned from elephantine bamboo in the afternoon. In the bathroom, someone had remembered to put a box of matches beside the candlestick on the lip of the sunken tub, faced in tiny mosaic tiles the same jade as the sea.

Personnel is professional if occasionally maladroit. (Note to check-in clerk: lose the lecture about how all tips are included, but guests can leave more if they like.) Babe Paley abandoned Round Hill against her will because her husband preferred Nassau's cooler climate for playing golf. Today it's the terrace of the resort's Plantation Grill, which has plastic furniture and synthetic napkins, that might have sent her packing.

And yet, and yet. For its confident air of tropical and colonial chic, Round Hill is unbeatable.
Rte. A1, Hanover Parish, Montego Bay; 800/972-2159 or 876/956-7050, fax 876/956-7505; villa suites with pool $700 in high season; Pineapple House doubles from $390.

tryall club
A few curves west along the coastal road, Tryall is as different from Round Hill as it is similar. The same concept is at work—rentals in the form of 56 individually owned two- to six-bedroom villas with pools.

The difference is that Tryall is a top-flight golf resort whose mahogany-trimmed white stucco villas are never shared. In addition, staff members are in tippy-toed attendance virtually around the clock, and meals tend to be taken "at home" rather than at the on-site restaurants.

Another difference: Tryall's gorgeously pitched grounds stretch over 2,200 acres. As a result, where Round Hill has a snuggly feel, Tryall impresses with its wide-openness—at check-in, breathing deeply of the wonderfully balmy air is an instant reflex. And while there is no hotel, there are 12 one- and two-bedroom Great House units, complete with kitchens, in a building adjoining the resort's nerve center, an elegant 19th-century stone plantation manor. While these much more affordable lodgings should not be ruled out, they unfortunately have the rather chilly, ghostly atmosphere of vacation condominiums.

Designed by Ralph Plummer, Tryall's 18-hole, 6,772-yard championship golf course is perhaps the best in the Caribbean, its only possible competition being the newer Trent Jones Jr. course at the Four Seasons on Nevis. Half the holes are among the hills, half on more level ground by the water. As New York Observer columnist Michael M. Thomas has noted, the links at Tryall avoid the "bulldozed, gouged look" of many contemporary courses. The resort's course is also famously uncrowded, with the number of rounds held to about 50 per day. For entertainment as well as refreshment, caddies are known to crack open coconuts with machetes mid-game. One veteran caddie, the much-photographed Hubert Russell, transports golf bags on his head.

Considering that each owner is responsible for the decoration of his villa, the low-slung houses have a surprisingly uniform look: cool, bright, and fresh, with lapses in taste mercifully few. Count on lots of wicker furniture, louvered shutters, local straw mats, lamps with cast or carved pineapple bases, and good squishy upholstery covered in juicy, four-alarm florals that would look hilariously garish almost anywhere else. Treillage is a big motif; it masks cathedral ceilings, edges towering canopy beds. As villas grow in size, so does the staff—to the minimum of three might be added a butler. Service is efficient and discreet in the best Jamaican tradition.

Accommodations offer an embarrassment of choice. Since so much of life at Tryall is lived out-of-doors, and since a three-shot par five is not everyone's idea of heaven, the size and orientation of the terrace should be a guiding factor when selecting a villa. Safety?The resort spends a reassuring half million dollars a year on security, including guards.
Rte. A1, Hanover Parish, Montego Bay; 800/742-0498 or 876/956-5660, fax 876/956-5673; two-bedroom villas $828 in high season; Great House suites from $500.

half moon
Founded in 1954 seven miles east of Montego Bay, Half Moon plays the size card—419 guest rooms, suites, and villas in Georgian-style buildings spread over 400 acres, with 52 swimming pools, six bars and restaurants, 13 tennis courts, and 86 full-time gardeners. Nearly 300 pounds of pineapple are consumed every day, and the workshops alone employ 10 people to produce the hotel's Queen Anne-style furniture and vividly patterned curtains, bedspreads, and cushions. The most elaborate of three wedding packages includes one set of La Perla lingerie, two bags of Blue Mountain coffee, and one aisle runner.

But not a single map of the property.

At least I never saw one during my 24 hours at Half Moon, and it sure would have been useful (apparently you have to ask). As the above numbers suggest, this is resort life on a potentially bewildering scale. A map is so crucial to understanding and enjoying the place, sending one out to guests should be a standard part of reservation procedure.

Of all the big-gun Jamaica hotels, Half Moon has the lowest style quotient. But it probably also delivers the best value for money. At $195 a night, my bottom-of-the-line "superior" had a chipped bathtub and twee heart-shaped cushions. But the sea view was so spectacular, Half Moon could ask $100 more for the room and not be accused of overcharging. A good diver could use the terrace as a springboard into the Caribbean.

The resort is big on kids, offering activities that are the opposite of run-of-the-mill, such as tree planting, reggae dancing, and classes in Jamaican patois. These distractions free up parents for golf, which is pursued almost as seriously as at Tryall. Molded from foothills, long on both bunkering and beauty, Half Moon's 18-hole, 7,119-yard championship course was designed in 1961 by Robert Trent Jones Sr. Beginners set on becoming middle-handicappers are in good hands at the hotel's David Leadbetter Golf Academy. Leadbetter "rebuilt" Nick Faldo's legendary swing and has sharpened the games of pros Ernie Els and Greg Norman.

Half Moon also rebuilds self-esteem. Pulling under the porte-cochere, which is only slightly less grand than the White House's, is a pure act of ego-fluffing.
Rose Hall, Montego Bay; 800/626-0592 or 876/953-2211, fax 876/953-2731; doubles from $195.

jamaica inn
Peter Morrow, whose Jamaica Inn is cast in his own determinedly preppy image, estimates that last season the hotel "turned off" 20 to 30 percent of its potential clientele with a dusty bylaw requiring that men wear a jacket and tie at dinner. This season, amid the grumblings of 30-time repeat customers who still love cha-cha-ing (and sweating) under the stars in tuxedos, the regulation has been relaxed. Ties are now optional.

"Imagine you're one of those wired Young Turks who put on a suit every day to go down to Wall Street," reasons Morrow. "Is buttoning your top button any part of your picture of a winter vacation in the sun?The answer is no. After a hotel in Antigua retired its tie policy last year, we were the last place in the Caribbean with one on its books. Our five-piece dance band is so bad it's good, if you know what I mean, but I wouldn't think of getting rid of it because we've had one for forty years. Still, I've got to bring the hotel forward."

Not too forward and not too fast, the core constituency of old-timers pray, worrying about the butter curls on their crustless white toast and bacon bits in their salads. Situated 70 miles east of Montego Bay in Ocho Rios, Jamaica Inn is fronted by a private, 700-foot beach dusted with silky sand, the diamond in the hotel's tiara. The beach is enclosed by rocky spits that rustle with vegetation and conjure the marvelously exclusive feeling of an enclave. Donning red jackets with gold braid, smiling waiters—some with 25 years of service at the resort—appear under the punishing noonday sun to tempt guests lounging beneath thatched umbrellas with—peanuts! In a deliciously retro gesture, the salty snack is doled out with a lemonade spoon from linen-lined silver dishes. Eat up, because at dinner the kitchen may try to pass off Sea Legs as crabmeat.

Of the 42 guest rooms, 3 suites, and one cottage, "premier" accommodations are the way to go. They have fully furnished living areas that are bigger than a Manhattan studio and completely open on one long side to the sea or beach. In the beach wing, only chunky, whitewashed balustrades stand between the sand and these charming, highly civilized, stage set-like verandas, appointed with terrazzo tiles, mahogany writing tables, and wing chairs and sofas. Fabrics are in the tonic Lilly Pulitzer taste.

Morrow has a tough row to hoe. On the one hand, by changing the dress code, he is openly courting the frisky MTV generation that throngs Negril up the coast. On the other hand, the last thing he wants is to alienate the croquet crowd. It's too early in the season to tell, but Morrow is convinced that both groups can find happiness at Jamaica Inn.
Main Street-Old Road, Ocho Rios; 800/837-4608 or 876/974-2514, fax 876/974-2449; doubles from $525 in high season.

chris blackwell's future classics
Island Records founder Chris Blackwell launched and nurtured the careers of Bob Marley, Steve Winwood, and U2. In his latest role as hotelier, Blackwell oversees a clutch of hipper-than-thou properties in Miami Beach, the Bahamas, and the Jamaica he still calls home. Since none of the Jamaican resorts in his Island Outpost portfolio is more than five years old, it seems a little premature to call them classics. But future classics?That sounds just right to us.
(800/688-7678 for reservations.)

Quietly folded into the Blue Mountains, at an elevation of 3,100 feet, Strawberry Hill's 12 vernacularly correct 19th-century-style cottages command heart-stopping views of Kingston. Other defining touches: magnificent fretwork, mahogany four-posters, heated mattress pads, a first-rate Aveda Concept Spa, balletic hummingbirds, and cascades of screaming bougainvillea.
Irish Town; doubles from $280.

The Caves' 10 tranquil wood-framed, thatched-roof cottages—lightheartedly decorated with batiks, mosquito netting, and vivacious colors—sit high above the sea on volcanic honeycombed cliffs. Snorkeling is excellent, and sea-salt exfoliation treatments are administered in grottoes.
Lighthouse Rd., West End, Negril; suites $500 in high season.

Rooms at Jake's, a 12-cottage mini-resort (stylishly marooned on Jamaica's remote and fabulously untouristed southwestern coast), don't have phones, televisions, or air-conditioning—and whether or not there's a beach depends on the degree of damage done by the last hurricane. But international funksters from the East Village to the East End can't get enough of this Mykonos-and-Marrakesh-flavored getaway.
Treasure Beach, St. Elizabeth; doubles from $75.

Ian Fleming wrote 12 of his James Bond thrillers at Goldeneye, his 15-acre waterfront estate just east of Ocho Rios. But these days, the main house (there are also eight new bungalows) has been zapped into what its designer calls a three-bedroom "tribal crash pad," perilously priced and jammed with the kind of outsize luxuries meaningful only to rock stars.
Oracabessa; Fleming house $3,500 with meals, one-bedroom bungalows $750.