Walking into Round Hill’s classic, open-air lobby, I had an immediate emotional connection and a sense of nostalgia swept over me. The view off the sweeping porch is palm trees perfectly placed on a manicured lawn supported by a backdrop of the sparkling blue Caribbean Sea.
Head concierge Kingsley Blake has been welcoming guests to Round Hill for 42 years. When he greeted me, he was sporting a bright turquoise jacket, and his warm Jamaican manner was infectious. He handed me a glass of fine rum punch and put me on notice that I was here to relax.
Kingsley explained that Round Hill began as the dream of John Pringle, a well-connected, Jamaican-born entrepreneur. The 110-acre peninsula was home to a plantation estate and pineapple groves.
In 1953, Round Hill Hotel & Villas opened as a luxury boutique cottage compound to appeal to the rich and famous who wanted a West Indies vacation home without the trouble of absentee ownership. Pringle invited prominent American and European socialites, literati and artists to build private cottages. It was the first of its kind in the Caribbean, and famous guests from then and now have made the resort their favorite place to vacation, including Cole Porter, Paul Newman, Grace Kelly, Paul McCartney and Meryl Streep
Fast-forward 61 years: The hotel operates on the same basis, with 36 ocean-front guest rooms and 27 villas owned by private shareholders. When the owners are not in residence, villas are available for rent. Villa owners Ralph and Ricky Lauren have taken a personal interest in helping reshape Round Hill and enhancing its old-school character.
The best way to describe Round Hill is elegant, understated, discreet, sophisticated and well-appointed. Service is impeccable, with a feeling of warm Jamaican hospitality. Many guests return year after year, and the tenured staff knows them by name.
The Pineapple House features 36 plantation-style guest rooms, all overlooking the Caribbean. Recently renovated and redesigned by Lauren with four-poster mahogany beds and white-on-white décor, the upstairs rooms have vaulted ceilings. Many have French doors that open onto private terraces. The spotless, spacious bathrooms feature Waterworks fixtures with deep soaking tubs and walk-in showers. WI-FI is available throughout the property, but thankfully there are no TVs in any of the guest rooms. The Pineapple Room is available for a fix of your favorite show or to watch the big game.
The 27 privately owned villas are decorated to the personal tastes of their owners. Villas for rent feature two to six bedrooms, living rooms, verandas, and views of the Caribbean Sea; 24 have private pools. Guests can book private villas complete with dedicated staff.
In 1953, John F. Kennedy, the young senator from Massachusetts, brought his bride, Jacqueline Bouvier Kennedy, to Villa No. 10 for their honeymoon. He returned in 1960 to Villa No. 25, where he wrote and practiced his inauguration speech.
The Round Hill grounds are flawless. There is a double-edge infinity pool that seems to spill directly into the ocean below. The beach is perfect for a sunset stroll or a cocktail at one of the tiki-style bars.
The spa and adults-only pool is a 10-minute walk from the main part of the resort on a winding, narrow path along the ocean surrounded by hanging vines and dense jungle. Housed in a former 18th century plantation home and surrounded by 10 acres of lawn that descend down to the ocean, the spa offers a variety of treatments and massage, along with a full-service beauty salon and a fitness center complete with personal training and ocean-side yoga, cardio, and body-sculpting classes. Request massage therapist Winsome for a signature mix of Swedish and Thai techniques with Jamaican aromatherapy oil — it hurts so good.
Round Hill embraces families, offering kids’ programs and nanny services. At the end of each day, afternoon tea is served for all. Children are picked up at the Pineapple Kids’ Club and join parents for cookies, cakes and juice served at the seaside bar.
Directed by James Beard Award–winning chef Martin McGinley, the food is top-shelf. Breakfast is set beneath almond trees on a seafront terrace. Dinner is either in the open air or higher above the sea in the new Grill at Round Hill, featuring contemporary Caribbean cuisine.
The resort recently returned two of its 110 acres to organic gardens and offers farm-to-table dinners. The kitchen garden and orchard account for nearly a third of the produce served on the resort. Each Monday, the whole resort heads to the beach for lively barbecue with flowing rum punch, grilled lobsters and a steel-drum band — a night worth planning your trip around.
The bar at Round Hill is as elegant as when the jet-set crowd came here in the 1950s; the old photographs that adorn the walls feature famous faces enjoying the beach and nightlife. Live entertainment from local magicians fills the atmosphere each night.
There is more than enough to do on the property besides lounging at your private villa pool. Round Hill offers such activities as snorkeling, kayaking, paddleboarding, windsurfing and glass-bottom boat tours. If you want more action off-property, shopping, golf, scuba diving, white-water rafting and zip-line adventures are all within minutes of the front gate.
Longtime Managing Director Josef Forstmayr has done a brilliant job preserving the special appeal of Round Hill by maintaining the best of the past without compromising what today’s world-class travelers expect. It’s no wonder guests return over and over again. Exclusive, exceptional and elite, this is a true five-star experience, but not in the way of Viceroy, Ritz-Carlton or Four Seasons. At Round Hill, the authenticity and soul shine.
