Driving up the road to Round Hill Resort and Villas in Montego Bay, Jamaica, one is greeted first by the casuarina trees. Gracefully swaying in the breeze, they are a perfect omen of what’s to come: easy, understated sophistication.
The plantation-style welcome room features the resort’s signature white and emerald green cabana stripes, accented by retro black-and-white checkered floors, with the veranda leading out to the stunning Caribbean Sea. Even when simply checking in, welcome rum punch in hand, it’s hard not to feel as glamorous as the resort’s iconic guests like John F. Kennedy, Jackie Onassis, and Paul Newman. To look the part, wear white linen, Ray-Ban Clubmasters, and espadrilles (leave the flip-flops at home).
Opened in 1953, Round Hill has spent the past 60-odd years garnering a legendary reputation in Jamaica and across the entire globe, being named the World Travel Awards World’s Leading Villa Resort 13 years in a row and earning the AAA Four Diamond Award of Excellence. The property consists of 27 classic and contemporary villas, as well as a 36-room beachfront hotel designed by Ralph Lauren, who also keeps his 20-acre vacation home here.
Hopping in the back of a golf cart, it’s a quick jaunt up to the legendary Villa 10. With four stunning suites spanning three levels, each with garden or ocean views (two rooms with both), it’s no wonder this is the villa that Kennedy and Onassis chose for their honeymoon. Many of the homes are now privately owned and are rented throughout the year, and each owner’s personal but elegant touches remain on display for guests. At Villa 10, Matisse prints, leather-bound books, and family photos with Sigourney Weaver give a visitor the feeling that she is simply crashing at a good friend’s impossibly gorgeous tropical cabin.
The upstairs bedroom at Villa 10 features a deep-set tub overlooking the manicured garden and ocean; if one prefers to bathe standing up, downstairs there is a secluded outdoor shower (just beware of falling avocados). And down a few rose bush-lined stairs at the edge of the garden is the villa pool. With no infinity pool extravagance, this offering is unfussy and completely private—perfect for mid-afternoon dips.
Of course, one doesn’t come to Jamaica just to go swimming—one comes ready to eat. The beachfront Restaurant at Round Hill is manned by chef Martin Maginley, who takes inspiration from the island’s classics (curry, jerk, roti) and presents them with sophisticated flair. An evening meal of lobster curry with a glass of chardonnay is the perfect way to start off a few long, leisurely days at Round Hill. Before lights out, simply fill out the breakfast form waiting on the nightstand; in the morning, chefs come right to the villa kitchens, awakening sleeping guests with the smell of brewing Jamaican Blue Mountain coffee and the perfume of mangos and papayas.
Tennis is the activity of choice at Round Hill, but the nearby Tryall Club as well as Half Moon both offer world-class golfing. The Spa at Round Hill, located a quick seaside stroll across the cove, hosts its own range of activities: island classics like hot stone massages, as well as enhanced anti-aging facials.
Leading the charge is hospitality veteran Josef Forstmayr, managing director of the property. “We want you to fall in love with Round Hill, but to keep you coming back, you need to fall in love with the island,” he explains as dinner is prepared back at Villa 10. As the sun dips below the palms, and the warm evening wind picks up ever so slightly, it’s difficult to think about anything other than wanting to see the sun rise one more time, at Round Hill.