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Inside The Tryall Club: Jamaica's Billionaire Playground Of Heritage, Sport And Elegance
The Great House at The Tryall Club stands as the estate's architectural and cultural heart—a former 19th-century sugar plantation house, now lovingly preserved as a symbol of Jamaica's layered history and refined hospitality. Nigel Lord Photography
Above the undisturbed coastline just outside Montego Bay, The Tryall Club is where history lingers in the breeze and luxury is written in quiet strokes. Once an 18th-century sugar plantation, this member-owned Jamaican sanctuary has evolved into a rarefied retreat for those who prefer privacy over performance. It's a place where billionaires arrive quietly, stay longer and often return for generations.
In the 1950s William and Ida DeLisser sold what is now The Tryall Club to two American investors from Texas: future Texas governor Tom Connally and future senator Lloyd Bensten. The two imagined the estate as a members-only club, attracting international jet-setters, diplomats, and cultural tastemakers seeking an alternative to resort tourism. When Lennox Lewis, one of boxing's greatest legends, became the first prominent Black homeowner at Tryall, it was a watershed moment in the luxury club's evolution toward greater inclusivity. Many native-born Jamaicans are now villa homeowners.
Tryall became a destination with a carefully curated portfolio of more than 90 private villas, each owned, designed, and operated like a billionaire's mood board—from beachfront compounds showcasing arresting art collections to villas dressed in chic, coastal minimalism and everything in between.
'The estate offers an exclusive club that is close to the airport and secure, which adds to the sense of privacy and luxury, while still being part of a close and welcoming community,' said Hugh Benjamin, owner of the Pineapple House at The Tryall Club.
Owners rent their villas in weekly blocks, with rates ranging from $393 per night (Great House Villas) to $7,663 per night for stand-alone villas.
Jamaica's vibrant soul is woven into every moment. The staff's genuine warmth and time-honored traditions create a living tapestry of hospitality. It's a seamless symphony of past and present, where the island's rich heritage plays out in sunlit moments, slow afternoons, and an ease that lingers long after you've left.
Dating to the 1700s, a stone aqueduct and waterwheel stand as enduring symbols of The Tryall Club's storied past, a reminder of its roots as a working sugar plantation, and a treasured piece of Jamaican heritage. The Tryall Club
Still standing on the property: the 18th-century stone aqueduct and waterwheel, a majestic relic of the estate's colonial past, gracefully preserved with dedicated plaques. The land remembers. And it's this sense of rootedness that gives Tryall its soul.
Well-known to discerning guests but not widely publicized, The Tryall Club quietly hosts a steady stream of celebrities and industry titans. But you won't find bodyguards or entourages here. To them—as to everyone who returns year after year—this isn't a resort. It's a sanctuary, where first names are more common than fanfare, and privacy is part of the welcome.
Benjamin's life story offers a useful example. A native of Jamaica, he grew up there, left and now owns a home in New York in addition to his villa at Tryall. Guess which home he visits to get away from a fast-paced lifestyle.
'Celebrities and industry titans have specifically chosen the Pineapple House villa as their destination because of its unobstructed panoramic view of the Caribbean Sea from each bedroom as well as the pool and dining areas,' Benjamin said. 'The views are magnificent, and our VIP guests note that the villa's architecture, curated furniture and Caribbean artwork, five-star amenities, and world-class staff truly make their stay at Pineapple House a personalized experience.' The Tryall Club's Sport Legacy: Where the Court and Course Matter
Framed by the Caribbean Sea and the lush hills of Hanover Parish, The Tryall Club's 18-hole course is one of Jamaica's most storied and scenic places to play. The Tryall Club Great Golf At The Tryall Club In Jamaica
Golf, too, is more than an amenity at The Tryall Club—it's a legacy. The 18-hole championship course, designed by Ralph Plummer in 1958, has hosted global events like the Johnny Walker World Golf Championship, and today includes a popular junior golf clinic, nurturing the next generation of players who may one day return as villa owners themselves. Many owners and visitors arrange cocktails and golf soiree just before sunset.
A new program, The Social Swing, is formally debuting this year. (Look to book the package on the website later in 2025.) The concept is for guests of all golf levels to enjoy three holes with a bit of socialization and great drinks. Think of it as a happy hour gathering where guests enjoy cocktails while taking a few easy swings on three of the holes on the resort's championship golf course.
It's less about the competition and more about the camaraderie—pairing the joy of play with the pleasure of good company and Jamaican-inspired refreshments.
'What makes golf at Tryall so special is the setting,' General Manager Kenton Jones said. 'You're playing along the sea, through the hills, and incredible, historic spots like our old aqueduct. It's a beautiful, relaxed course that still offers a great challenge, whether you're a serious golfer or just out to enjoy the views and a good time with friends.' Great Tennis At The Tryall Club, Jamaica
Tennis with a View: Set against the lush backdrop of Jamaica's northwest coast, The Tryall Club's championship courts blend sport and scenery in equal measure. The Tryall Club
Far from a leisure-only property, Tryall is ranked among the Top 10 tennis resorts in the Caribbean. It's not just a bullet point in a marketing campaign. Tennis is integral to the club's culture. With nine courts, expert instructors, and tournament-quality programming, it's as serious as it is serene.
'It's a big part of the Tryall lifestyle: friendly matches, daily clinics, and a really welcoming tennis community,' Jones said. The Nanny Program At The Tryall Club
Play as many rounds of golf and tennis as you can fit in a day. The Tryall Club's uniquely equipped nanny program is beloved, and appropriately elevated—think less babysitter, more Caribbean Mary Poppins. Trained childcare professionals become part of the family's experience, allowing parents to unwind while children are engaged, cared for, and safely entertained.
'It gives parents peace of mind knowing their kids are in great hands, whether they're in the villa, at the beach, or exploring the property,' Jones said. 'It makes it easy for everyone in the family to fully relax and enjoy their time here.' Dining At The Tryall Club
Ooshan Bar & Restaurant, the newest addition to The Tryall Club, has quickly become its crown jewel for dining—both a culinary and an architectural standout. The Tryall Club
Sitting right on the edge of the Caribbean is the Ooshan Bar and Restaurant at The Tryall Club. The architectural standout opened in November 2024 and has quickly become the club's crown jewel for dining. The bar is a buzzy and boozy affair from 5 to 6 p.m. daily, where guests and locals gather in a ritualistic ceremony to visit and try some of the clever cocktails (like the Tropical Storm and Drunken Pimento) for which Ooshan has become known.
Complementing the Beach Club, just steps from Ooshan along the beach, is the Beach Bar and Grill. This casual outpost delivers exactly what its setting promises: pizza, salads, burgers and baskets of onion rings, chicken wings and fish and chips. The atmosphere is relaxed, unfussy, and unmistakably Jamaican; barefoot and covered in sand is just as okay here as a linen cover-up. Throughout Tryall, the rum punch is fabulous. Don't hesitate to have a few (or many). The Spa At The Tryall Club
The recently opened spa at The Tryall Club is a peaceful retreat that reflects the restorative energy of Tryall. The Tryall Club
Livity Spa by Tryall Club, which opened at the end of 2024, blends holistic wellness with focused, results-based treatments. Guests can choose from an expansive menu designed to promote balance and vitality, while also offering space for stillness and reflection. Offerings range from massages and facials to sound meditation, a restorative practice that uses harmonic frequencies to quiet the mind and support nervous system regulation.
The spa was designed to feel completely connected to nature: open-air treatment spaces, ocean views, and the sound of the waves in the background. The island's restorative nature is reflected in the peaceful and intimate calm of the spa.
'People come for a massage and end up staying to just soak in the surroundings," Jones said. The Private Villas At The Tryall Club, Jamaica
Celestial Villa at The Tryall Club in Jamaica offers five stunning bedrooms for up to ten guests and the most stunning ocean views. The Tryall Club
With more than 90 privately owned villas ranging in price from $1 million to $5 million (and up), there's a footprint for nearly every size family. Villas range from one to two bedrooms up to the expansive 10-bedroom stand-alone villas that reflect the owner families.
'Villas offer a mix of amenities including private pools, gyms, game rooms, and more,' said Nicola Delapenha, a Coldwell Banker luxury property specialist. 'Each comes with a dedicated staff, combining the comforts of a private home with resort-style service. Styles vary, but all reflect the relaxed, elegant spirit of the Caribbean.'
The customer base for The Tryall Club largely consists of North Americans, especially from the U.S. and Canada. International clients from the U.K. and Europe, and local Jamaican homeowners round out the mix. According to Delapenha, each family is reflective of a customer type: affluent families, business leaders or celebrities seeking luxury, privacy and a multi-generational retreat. Celestial Villa At The Tryall Club, Jamaica
At Celestial Villa, indoor and outdoor living converge—the view from the great room flows seamlessly to the private pool and onward to the Caribbean Sea. The Tryall Club
The chic, airy oceanfront design of Celestial Villa is accentuated with the precision of fine British tailored service. The staff, the unseen gears that keep a house humming, is worthy of Downton Abbey. Laundry is attended to daily, even on-demand, while the housekeeping staff operates with a relaxed yet relentless efficiency.
The chef at Celestial—a culinary goddess who conjures soulful meals, steeped in love and legacy—reigns supreme over the kitchen. There's also a nice selection of daily treats, from freshly baked banana bread and blueberry cobbler to chocolate chip cookies and pound cake. Each dish is a whispered reminder of Jamaica's rich sun-kissed heritage. Add the cinematic backdrop of the Caribbean with every bite. Aqua Bay Villa At The Tryall Club In Jamaica
Aqua Bay, owned by the founders of the Sandals Resorts brand, is a crown jewel at The Tryall Club. The sanctuary space sits right on the ocean and includes its own private cinema worthy of a studio mogul, a fully-fitted gym and a luxurious spa suite with two massage tables. More than a simple accommodation, Aqua Bay is an empire of repose.
In a world of hyper-marketed destinations, The Tryall Club offers the ultimate luxury: relevance without reinvention. It remains a place of private legacy and personal return, where families, billionaires, and lovers of timeless design come not to be seen, but to live well, quietly. Jamaica's vibrant soul is woven into every moment here. The staff's genuine warmth and time-honored traditions create a living tapestry of hospitality, a seamless symphony of past and present.
