The Tryall Club: Jewel of the Caribbean

Life is sublime at The Tryall Club, home to lavish hilltop villas, four kilometres of prime beachfront, and a newly restored Ralph Plummer course that has reigned as the flagship of Jamaican golf since the 1960s.

(Last updated January 2024.)

Ewan Peebles still vividly recalls watching a television interview with Nick Faldo after his victory in the 1992 Johnnie Walker World Golf Championship at The Tryall Club. “Swaying palms, cloudless skies and the turquoise Caribbean Sea,” says Peebles. “Jamaica seemed like a beautiful dream to a sixteen-year-old growing up in wintry Scotland.”

Jump forward and Peebles is now the director of golf at a Ralph Plummer-designed course long regarded as one of the Caribbean’s best. The prestigious Johnnie Walker, an invitational featuring the PGA Tour’s highest earning players, was played at Tryall for five years starting in 1991. And the LPGA Tour’s Jamaica Classic called the resort home from 1989 to 1991.

Opening with a tee off near the sea before climbing through coconut groves and returning to the shore, Tryall’s recently renovated golf course is the centrepiece of an ultra-exclusive 890-hectare resort on Jamaica’s northwest coast that includes almost four kilometres of waterfront.

Owned by billionaires and the merely wealthy, the 90 villas at Tryall are found on the oceanfront or atop and down the hillsides of a former sugar plantation thick with coconut palms, bougainvillea, and fruit and flowering trees. The Flint River, fed by mountain springs, winds through the property before flowing into Tryall Bay, where a cannon and jetty recall the days when British redcoats defended Jamaica against the French, Spanish and a devil’s brew of brigands.

Many of these sumptuous villas are available for rent when the owners are not in residence. High season (from the Christmas holidays to just past Easter) prices climb as high as US$45,000 a week. Each villa enjoys a dedicated staff, including a butler, chef, and head housekeeper who tend to guests around the clock. Also available are one- and two-bedroom condos in the Great House (starting from US$3,500 a week in high season). Built in 1834, the colonial-style heritage building serves as the property’s main reception area.

My wife, Sharon, and I are happily ensconced at Point of View, a one-storey, six-bedroom villa high atop Barnes Hill. The villa’s blend of burnished mahogany furniture, walls made of local stones, and exquisite Jamaican artworks is a celebration of classic Caribbean style.

Open to the tropical breezes, our large sitting and dining room overlooks an infinity pool and offers breathtaking views of the distant coastline. At night, as our butler serves another al fresco gourmet meal, we amuse ourselves by counting the brightly lit cruise ships departing from Montego Bay, about 19 kilometres to the east.

Life is sublime at Point of View. Every morning Sharon plans the day’s menu with our chef, Marlon Mills, who has cooked at top Jamaican resorts. Perhaps jerk chicken, an island classic, or a deliciously spicy red snapper escovitch? Sharon and Marlon then stroll down the hill to our kitchen garden, where they choose the salad ingredients of the day.

Far from Kingston, the exciting though crime-plagued capital city, the welcoming Jamaica promised in the travel brochures is readily found on this gorgeous and sun-drenched coastline.

In the years following World War II, Jamaica and in particular the Montego Bay area became a haven for jet-set celebrities seeking a Caribbean playground. Truman Capote, Katherine Hepburn, Graham Greene, Marlene Dietrich, Grace Kelly and high-society mavens like Babe Paley and Slim Keith joined the winter-long carnival. After docking his yacht in Jamaica during a storm, Hollywood swashbuckler Errol Flynn put down roots on land he won in a booze-fuelled poker game.

Still a resident of sorts, entertainer and bon vivant Noël Coward is buried at Firefly, his simple, one-bedroom winter home overlooking St. Mary Harbour and the Blue Mountains near Ocho Rios. The site originally belonged to the pirate Henry Morgan.

Coward’s neighbour, James Bond creator Ian Fleming, lived in a three-bedroom villa he named Goldeneye. Tourism soared after the first Bond movie, Dr. No, was filmed in Jamaica. The indelible image of Ursula Andress rising out of the sea in her white bikini launched a million male fantasies—and attracted at least as many tourists to an island becoming famous for its reggae music, Blue Mountain coffee and high-proof rum.

Through the years Tryall and three other high-profile golf courses opened near Montego Bay to accommodate the flood of free-spending tourists. Today, Jamaica’s northwest coast is widely regarded as one of the Caribbean’s most attractive golf destinations.

Just east of Montego Bay, Cinnamon Hill Golf Course tumbles down the slopes of Mount Zion to the sea. Golfers at this popular Robert von Hagge-Rick Baril design are treated to several unforgettable holes as the course wends through the 18th- and 19th-century ruins of Rose Hall plantation. A waterfall behind the 15th green was featured in the James Bond movie Live and Let Die. And the 14th hole offers a close-up view of the former holiday home of singer Johnny Cash, a man beloved by the locals for his generosity to Jamaican charities.

Still further up the slopes of Mount Zion is White Witch Golf Course. Golfers might need a bracing shot of high-octane rum after their first look at a treacherously difficult von Hagge-Baril design routed through rocky outcroppings and gaping ravines overlooking the distant sea.

White Witch is aptly named after Annee Palmer, Jamaica’s notorious “White Witch,” who was mistress of Rose Hall plantation in the early 19^th century. Palmer was said to have murdered three husbands, as well as several unfortunate slaves whom she had tired of as lovers. Horrified servants strongly suspected their evil mistress of dabbling in witchcraft.

A far less nerve-racking round of golf can be enjoyed at nearby Half Moon Golf Course. This classic Robert Trent Jones Sr. design is one of the many attractions at luxurious Half Moon resort, whose high-society guest list has included Queen Elizabeth II and John and Jacqueline Kennedy. Opened in 1961 (and masterfully updated by Roger Rulewich in 2005), Jones’s course flows seamlessly through gentle foothills just beyond the craggy coastline.

But it is The Tryall Club—host to Faldo, Greg Norman, Arnold Palmer, Nancy Lopez, Seve Ballesteros, Ernie Els, Patty Sheehan and other giants—that has reigned supreme in Jamaican golf since its launch in 1960.

Red-hot American golf architect Andrew Green oversaw a four-year redo that included the installation of a new irrigation system, the rebuilding and defining of bunker complexes, and the enlarging and levelling of greens. Especially on the hilly back nine, time and gravity had severely sloped the putting surfaces, making them extraordinarily difficult to read.

Despite the changes made by Green, who earned raves for his revamp of the historic East Course at Oak Hill Country Club prior to the 2023 PGA Championship, Tryall is still very much the golf course built by the late Ralph Plummer.

The Texas-based Plummer, who worked on more than 100 courses during a 40-year career, carefully fit his 6,836-yard layout to the existing landscape. Tryall flows to the sea and then, eight holes later, rises to an elevation of 180 feet. Towering palms and other trees often serve as hazards, and greens are sited where they are subject to brisk trade winds. The greatest challenge for golfers comes from the landscape’s natural slopes and turns.

Absolutely unforgettable is the par-four seventh hole, one of the most photographed in the Caribbean. Golfers playing the back tees must somehow ignore the distraction of a still functioning 300-year-old waterwheel to hit a precision shot through the stone pillars of an aqueduct.

Golf is as much a part of life at The Tryall Club as its magnificent villas and ocean views. Many villa owners, who fly in from around the world and collectively own the entire estate, are so proud of their course that they rarely leave the property to play Half Moon, Cinnamon Hill or White Witch, despite their considerable attractions.

From its start in 1957, following the plantation’s purchase by a group of Texas businessmen, The Tryall Club was intended as an exclusive and totally self-contained playground. All that villa owners and guests might desire is found on property, including nine tennis courts, an excellent beachfront restaurant, a market that stocks organic foods and fine wines, and a staff happy to arrange on a moment’s notice a snorkeling or deep-sea fishing expedition.

Villa owners, some of whom have been coming to Tryall since they were children, enjoy socializing with their neighbours and are welcoming to even short-term guests. They hop between villas to share epicurean dinners or to enthusiastically organize annual fundraisers for Jamaican charities. In their admittedly biased opinion, The Tryall Club represents the best of everything the Caribbean has to offer—from tropical gardens and architecture to its golf course, caddies, greenskeeping staff and Scottish-born director of golf.

Ewan Peebles arrived at Tryall in 2011 following a stint in the same role at Half Moon. In 2018, he thrilled the membership when he shot a course record 61, a remarkable feat considering the illustrious golfers who have played here. Peebles, who makes a point of playing with club members as often as he can, is a three-time PGA Jamaica Champion.

What Peebles most appreciates about life at Tryall is the warmth and positivity of the Jamaican people. “Many don’t have much, but they truly love life,” he says.

The icy winters of his boyhood in Scotland are now a fading memory. Looking out over Tryall’s emerald fairways to the crashing Caribbean Sea, Peebles smiles and says, “There are still days when this place takes my breath away.”