Designed to Travel: An Inside Look at Round Hill
Interiors maven Christine Gachot and her fellow designer husband, John, open up their travel diaries
Tucked in a secluded cove above Montego Bay, Round Hill is one of my favorite places in the world. Since opening in 1953, this storied resort—where President Kennedy penned and practiced his inauguration speech in Villa 25—has hosted its fair share of notable guests; Grace Kelly, Truman Capote, Alfred Hitchcock, and Ian Fleming were among its frequent visitors. To this day, Round Hill continues to offer an elusive blend of timeless luxury and tropical charm.
For me and John, who have been visiting for decades, the resort’s history, along with its Caribbean climate and dramatic landscape, is deeply inspiring. We first decided Round Hill would be our place because of our own family’s personal history here—John’s grandparents were regulars. And so, this tiny corner of Jamaica has become our home away from home. We visit to disconnect from our incredibly satisfying, but chaotic, New York City work lives—when a creative reset is needed. Though we’ve explored every corner of Jamaica, nothing resonates more deeply than hearing our beloved host Kingsley say, “Welcome home.”
The island’s undercurrent of sound is a symphony in the background of our days and nights—birds chirping in the breeze, mangos hitting the shingled roof of our cottage, and the love songs of tree frogs at night. The constant soundtrack is lulling, and each day spent here allows us to sink further into soft relaxation.
Making an entrance…
The Round Hill experience begins immediately at Sangster International Airport, when our hotel driver warmly meets us with a smile and two chilled Red Stripes. As the car whisks us through the small towns of the Caribbean landscape, I begin to feel both excited and relaxed at the same time. We’re back! The resort sits on a secluded peninsula overlooking Montego Bay’s aqua-blue waters, surrounded by deliciously vibrant and lush foliage. The main hotel and its villas dotting the property combine traditional Jamaican colonial architecture, creamy white walls, and steep shingled roofs, with the luxurious and elegant aesthetics of Ralph Lauren.
And wow—arriving at the property always feels like stepping into a dream. The tree-lined alley leading up the hill, with the clear blue water glimmering in the distance, is every bit as iconic as the hotel itself. I approach the green and white awning to take in the view to the beach, along with familiar faces at the front desk, which remains nearly unchanged in all of its 70 years.
The ever-welcoming team greets us by name and with a hug, offering chilled eucalyptus towels and crisp glasses of the house rum punch upon our arrival. Although our villa is ready, we opt to indulge in another welcome drink, the first of many swims, and fresh fish tacos at the Tree Bar. We also need to say hello to our friends and check in on local resident celebrity, Otis the duck. We’re just getting started!
Come hungry…
Dining options are aplenty, and all of them exceptional. From casual beach bars—my favorite lunch spot—to gourmet dinners, there is something for everyone. The culinary program is led by executive chef Martin Maginley, who reimagines local Caribbean cuisine with a modern twist using only the freshest ingredients—produce is plucked straight from the onsite garden. If you’re staying in a villa, don’t miss breakfast—it’s an experience in itself. The menu is simple and lovely: vibrant platters of fresh fruit (perfect for nibbling throughout the day), eggs cooked to order, fluffy pancakes, and baskets of the most irresistible homemade pastries.
John and I especially enjoy afternoon tea served at the cocktail bar. It’s the perfect pause from the sun—a chance to sip a pre-dinner cocktail, enjoy lovely canapés and small bites, play a round of backgammon, and chat with fellow guests. A collared shirt is required, but John doesn’t mind, it’s all part of the charm. Most evenings, we dine at our villa, where the house cooks prepare meals to order. Menus are planned the day before, provisions are gathered that morning, and the kitchen fills with heavenly aromas throughout the day—shrimp, freshly caught local fish, and more. After so many years, they know us well; I don’t even need to mention that I don’t eat meat.
If you’re staying at the hotel proper’s Pineapple House, be sure to enjoy a dining experience at the Seaside Terrace, overlooking the ocean. Indulge in fun, themed buffet nights, candlelit and under the stars. And don’t miss the beach barbecue on Monday evenings, a cherished Round Hill tradition.
Rest your head…
Villa 23 and Villa 18 have become our true homes away from home. I even have the same little spot where I drop my keys each visit, and both villas are cared for by two of the most thoughtful teams at Round Hill. They know exactly where we like to tuck our luggage away, and they anticipate every detail with such grace. John and I have created some of our sweetest memories here, and the walls themselves seem to hold treasures from our past visits. On the shelves are books we’ve read by the private pool and a pair of porcelain hens that John once tracked down and gifted to me for our own home—personal touches from the owners that surely mean as much to other guests as they do to us. The warmth of Villa 23 feels so personal, as though you are staying in someone’s perfectly designed home, while the view from Villa 18 is straight out of a film set. And with the devoted on-site teams who cook, clean, and assist with such genuine care, you truly cannot go wrong with either.
As expected, relaxation comes easy nearly everywhere here, where sand, sun, and salty air create an enchanting atmosphere. And when it rains… even better. Thunder rhythmically rumbles like drums and thick raindrops permeate the cadet grey sky. It’s magic. Years ago, during one particularly rainy stay, I was initially disappointed. But, the feeling quickly melted away when I experienced the island’s energy shift into something equally as captivating, a current of dark and moody electricity. John is enamored, and he almost always sketches or paints when the dark clouds come rolling in. Now, I welcome the rain! The weather doesn’t matter here—it’s all great, and I truly mean that.
Make yourself at home…
Round Hill is sprinkled with all kinds of fitness and wellness offerings. Tennis and pickleball courts sit deep within the lush tropical setting, while a hiking trail—my personal favorite—loops through the property and offers the most stunning ocean views. There’s a myriad of water sports available—snorkeling, scuba diving lessons, paddleboarding, and windsurfing is all right there on property. If you’re seeking a more tranquil experience, the spa is not to be missed. Set overlooking the ocean on a sprawling lawn sit three pavilions and a serene pool, which are removed just enough from the main resort to feel like you are transported yet again. Even the procession to the spa and fitness area is special—lush, jungle-like vegetation surrounds a walking path that hugs the ocean and is marked with stone charms, wishes left from previous guests. It’s calmness at a higher level.
Yoga and fitness classes are offered in the outdoor pavilion, while a state of the art fitness center is housed in a climatized space. The spa itself offers a wide range of treatments; the signature house massage is award-winning. So don’t be concerned about the rum cocktails… you’ll have plenty of opportunities to work them off! Our boys grew up coming here, and while we’re now empty nesters, the resort offers a kids club for children of all ages, providing a wide variety of activities for any little ones tagging along. There’s also nanny service available for both daytime and late evenings, seamlessly integrating family time into adult fun.
That extra mile…
Each visit—no matter how many years pass—still leaves me in awe of the service and genuine generosity. Many of the team members have been here for over two decades, carrying with them a profound knowledge of the property and its spirit. They remember our favorite drinks, quietly unpack our suitcases without being asked, and always greet us with a warm smile and an easy laugh. From the gardeners to the ever-charming bar team, the service is polished and attentive, yet never overbearing.
The takeaway…
In a world where hotel options have grown into what feels infinite, few properties offer an authentic and unique experience. Round Hill is one of the few that has retained its original sense of old school glamour, with service to match. The entire experience is seamless and beautifully framed by the hotel’s history, tropical climate, and allure of the ocean.
Be generous to operations teams everywhere, but especially here, where the veteran staff has been delivering a consistently luxurious experience for the past 70 years. Treat all of the villas and common spaces like your home, because for many, this resort is our fantasy escape that we return to over and over. Filling it with positivity, love, and respect goes a very long way.
Don’t miss…
Introduce yourself to Kingsley Blake, the beloved ambassador of Round Hill. For more than four decades, he has been the embodiment of exceptional hospitality—welcoming guests with warmth, charm, and an unwavering commitment to their experience. His presence is part of the magic of Round Hill, where his genuine care and personal touch have become as legendary as the property itself.
Pro-tip: Book the Blub Mo-Bay concierge service before you go for a seamless arrival. You’ll breeze through customs, collect your bags with ease, and be personally escorted through the airport.
Next time…
I’ll do it all over again, exactly as I always have.