The Great House at The Tryall Club: A Symbol of Jamaica’s History and Luxury
The Great House, at the heart of The Tryall Club, is a restored 19th-century sugar plantation house. It stands as a testament to Jamaica’s history and a beacon of refined hospitality. Overlooking Montego Bay’s untouched coastline, this estate is where history and luxury merge seamlessly.
A Rich History, A Private Sanctuary
Once an 18th-century sugar plantation, The Tryall Club has evolved into a private retreat for those seeking exclusivity. Its tranquil environment attracts billionaires and discerning guests who value privacy over prestige. Visitors return often, making it a generational haven.
In the 1950s, William and Ida DeLisser sold the estate to two Texas investors: future Governor Tom Connally and future Senator Lloyd Bensten. They envisioned it as a members-only club catering to international jet-setters, diplomats, and cultural tastemakers. When boxing legend Lennox Lewis became the first prominent Black homeowner, it marked a turning point toward inclusivity, with many native Jamaicans now owning villas.
The Villas: A Curated Collection of Luxury
The estate offers more than 90 private villas, each reflecting the personal style of its owner. From beachfront homes with stunning art collections to minimalist coastal designs, each villa embodies the luxury of its owner’s unique tastes.
«The estate offers an exclusive club that is close to the airport and secure, adding to the sense of privacy while being part of a welcoming community,” says Hugh Benjamin, owner of the Pineapple House.
Stay at The Tryall Club
Villas are available for rent in weekly blocks, with rates ranging from $393 per night (Great House Villas) to $7,663 per night for standalone villas.
Jamaican Hospitality at Its Best
The warmth of Jamaica’s people, combined with the island’s rich culture, makes every moment at The Tryall Club unforgettable. The staff’s genuine hospitality creates a seamless blend of tradition and luxury, offering an experience that lingers long after departure.
Book Your Getaway Today
Ready to experience the blend of history, luxury, and authentic Jamaican hospitality? Book your vacation at The Tryall Club and immerse yourself in an unforgettable stay.
MWR LIFE invites you to unwind and discover the magic of this one-of-a-kind estate.
Dating back to the 1700s, a stone aqueduct and waterwheel stand as symbols of The Tryall Club’s history, a reminder of its origins as a sugar plantation and a piece of Jamaican heritage.
The 18th-century stone aqueduct and waterwheel are still preserved on the property, maintaining a connection to the estate’s colonial past. These relics, marked by dedicated plaques, offer a sense of rootedness that gives Tryall its soul.
While The Tryall Club quietly hosts celebrities and industry leaders, it remains a sanctuary where privacy is valued over fanfare. First names are more common than bodyguards, making it a special retreat for those seeking peace.
Benjamin, a Jamaican native with homes in New York and Tryall, exemplifies the club’s appeal. He returns to Tryall to escape his fast-paced life, finding solace in its calm atmosphere.
Celebrities and industry figures often choose Pineapple House villa for its stunning panoramic views of the Caribbean Sea, as well as its top-tier amenities, personalized service, and Caribbean artwork. This makes the experience truly unique and luxurious.
The Tryall Club’s legacy also extends to sports, where the court and course are integral to the club’s offerings.
Framed by the Caribbean Sea and the hills of Hanover Parish, The Tryall Club’s 18-hole course is one of Jamaica’s most scenic spots for golf.
Golf here is a legacy. Designed by Ralph Plummer in 1958, the championship course has hosted global events like the Johnny Walker World Golf Championship. Today, it also offers a popular junior golf clinic, helping nurture future players who may one day become villa owners. Many visitors and owners enjoy cocktails and golf soirees just before sunset.
A new program, The Social Swing, debuts this year, offering a relaxed experience for golfers of all levels. Guests can enjoy three holes, socialize, and sip cocktails while playing. It’s more about camaraderie than competition, with a laid-back atmosphere and Jamaican-inspired drinks.
General Manager Kenton Jones highlights the course’s unique setting, saying, “You play along the sea, through the hills, and past historic spots like the old aqueduct. It’s a beautiful, relaxed course with great challenges for both serious golfers and those just looking to enjoy the views and good company.”
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.
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.
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.
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.
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.
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 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, 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.
