
By Marc Kristal
In the 1960s, when I was, as the saying goes, in short pants, I visited Montego Bay, Jamaica for the first time, in the company of my mother and younger brother. The family stayed in a modest hotel, and had a lovely time. We swam in the impossibly blue Caribbean, ate oxtail stew and did the limbo; I climbed Dunn’s River Falls in Ocho Rios and had my picture taken with water cascading onto my head.(I also received many gentle lessons from the hotel staff, regarding respectful ways to address chambermaids, waiters and porters, which remain with me to this day.)
My brother and I were perfectly happy – but our mother was not. All she wanted was to visit Round Hill.
Sited on a 110-acre peninsula on which planters grew coconut and allspice, Round Hill Hotel and Villas, which opened in 1953, was the creation of the Jamaican entrepreneur John Pringle (later the island’s first tourism director). It was Pringle’s idea to build a small inn along the beach of the 30-acre, amphitheatre-like property–the 36-room Pineapple House, named conceivably for the logo the hotelier sketched on a napkin–to be funded by developing small cottages on the grounds for individual investors. Pringle’s first taker was Noel Coward, whom he badgered into acquiescence in the course of a long plane flight; as that initial conquest suggests, Round Hill became legendary for its owners (ultimately occupying 27 villas) and guests, including Cole Porter, Alfred Hitchcock, Grace Kelly, and John F. and Jacqueline Kennedy. Photographs that still grace the bar, of white-jacketed gentleman and bejeweled ladies smoking, drinking, gambling, and generally living it up in classic self-destructivist style, suggest the storied shimmer that put stars in my mother’s (and so many others’) eyes.

At a long glance, Round Hill now looks much the same – as marketing manager John Bradway observes, half-century-old photos of the grounds might have been taken yesterday – and runs the same way, with shareholders renting their villas to hotel guests when not in residence. But in many ways, the place has decisively entered the 21st century. Consider the décor: In 2005, Ralph Lauren–owner of two villas–redesigned the Pineapple House guest rooms, retaining their midcentury Caribbean flavor while updating the style with a simple palette composed largely of white cotton and dark wood –a refreshing elegance the actress (and frequent visitor) Alfre Woodard calls “organic posh.” The designer’s hand is evident as well in the just-finished Grill at Round Hill, the new open-air restaurant composed of black granite floors, white tongue-and-groove columns and brass lanterns, which overlooks the current dining patio (as well as the magnificently landscaped hillside and sea) from the second floor.
Round Hill has also smartened its amenities, notably the beach, which has been widened and deepened, and the capacious negative-edge pool, constructed in 2006 from old stones and resembling a contemporary interpretation of a 19th-century cistern. The hotel hosts some thirty weddings a year – “a three-night minimum, and never two on the same weekend,” Bradway says – as well as business meetings; the newly renovated Hanover Room, a pavilion beside The Grill with an expansive terrace, serves both.
Most impressive is Round Hill’s spa, which opened in 2002. It is, in fact, not part of the original property, but installed in a remodeled, handsomely restored 18th-century great house called Welcome Wharf, commanding ten acres of lawn, and a five-minute walk from the hotel, along a path overhung with foliage and limestone outcroppings, beside the water’s edge.
Along with a fitness center and pool, the spa offers a very full complement of massages, facials, hand and foot treatments, body therapies, and skin renewal processes; the massage I received, from a petite, shy woman with hand strength the Boston Strangler would have envied, proved to be sensitively attuned to my aches and pains and thoroughly effective, and one of my traveling companions, following a liquid night, pronounced the special Hangover Massage, with its toxin-extracting Sweet Basil rub, a success.
Round Hill’s spa manager, the appropriately named Serene Sanders, introduced me as well to her newest innovation, a secluded hilltop “Garden Loft” behind the great house, veiled atavistically by tall trees and their long tendrils. Here couples can enjoy simultaneous massages, followed by champagne a deux as prelude to a romantic afternoon.
It’s questionable, however, whether one would choose Round Hill if romance were uppermost. The hotel is, rather, the sort of traditional, family-friendly resort that maintains a thoughtfully programmed Kids’ Club, “classic” Jamaican entertainments featuring limbo contests and a shirtless man in orange pants balancing a beach chair on his nose, and – despite the organic vegetable garden, of which Josef Forstmayr, Round Hill’s droll Austrian-born managing director, says, “Just having it – everyone feels healthier!” – over-thought cuisine that is less successful than the kitchen’s simpler vacation fare.
Yet if the louche jet-set glamour of yesteryear has passed, Round Hill nonetheless remains a paradise of palm and sea almond trees, and bright, fragrant flora (tended by 47 gardeners) surrounding impeccably maintained villas – 21 with private pools – and historic structures, all of it undergirded by service that manages to be at once unobtrusive and ever-present. “Everything happens naturally here – everything is easy,” Bradway says. One could not disagree.
The difference between Round Hill and Jamaica Inn, another storied, fifties-era hotel in nearby Ocho Rios, can be seen in the celebrities the latter attracts. Arriving at the estate-like property – two-story arcaded structures arranged in a loose U shape around a downsloping lawn and painted a distinctive periwinkle blue (Winston, one of the barmen, tells me later that the shade is custom-mixed) – I walked from the open-air entry to the top of the grand stair that leads down to the grounds, drawn by the sea view, and saw, ascending toward me, a woman so beautiful that my head snapped back. I was not, it transpired, alone in my estimation: it was Lisa Hanna, former Miss World (1993), presently a member of the Jamaican Parliament, and a regular Inn habitué. This siting was topped, shortly thereafter, by the appearance of the less comely but more notorious Anita Pallenberg, Keith Richards’ partner in life and heroin in the 1960s – entirely appropriate for a hotel that, during peak season, doesn’t take children under twelve.
Yes, the vibe is different at Jamaica Inn. Partly this derives from the fact that, though the property occupies only six acres – roughly a fifth the size of Round Hill – its public spaces feel much bigger, in large measure because the outsized expanse of rolling green, ringed with lush, colorful planting and including a croquet lawn, dissolves into a broad and deep, 700-foot-long private beach. (Indeed, according to owner Peter Morrow, whose family purchased the hotel in 1958, eight years after it opened, Morrow’s father added the lawn because there was too much beach.) The sea itself, in Jamaica Inn’s protected cove, is especially felicitous, with a sandy bottom that gently drops away to facilitate both wading and swimming.
Consequently, the experience remains all about beach, water and view: The 47 suites, as well as the restaurants, bar and library, overlook the grounds and Caribbean; and Morrow’s father enlarged the terraces for the first-floor accommodations to create fully furnished living rooms than encourage an indoor/outdoor life. (The hotel also maintains a small portfolio of one- and two-bedroom cottages on an adjoining bluff, fitted out with generous decks and plunge pools, and set its KiYara Ocean Spa invitingly at the bluff’s edge.)

Accordingly, whereas life at Round Hill, with its tennis courts, busy pool scene, and sociable villa residents, has a various, communal flavor, Jamaica Inn’s clientele seems happy to spend entire days beneath beach palapas, plastered to lounge chairs with no more company than a sunblock-and-sweat-sodden Vanity Fair. This is fortunate, as – unlike Round Hill, where the service owns the uniformity of excellence one associates with a multi-star establishment – each Jamaica Inn staff member has a distinct personality. Partly, one senses, this is deliberate. Peter Morrow told me that, when his family purchased the hotel, they inherited a core clientele of repeat guests that kept the place at capacity for decades; nine years ago, with the old crowd dying off, Morrow met the challenge by hiring Mary Phillips, who’d worked at Round Hill for over a decade, as general manager. Alternately affectionate and fearsome, Phillips – a sinewy, braceleted, sun-browned woman, trailed everywhere by her dogs Zion and I-And-I, and as big a character as any of her guests – has brought business back, at least in part, by encouraging the human individuality that gives Jamaica Inn its savor.
Yet the more one releases the expectations of the luxury traveler and embraces Jamaica Inn’s overlay of idiosyncrasy, the better time one has – and that, too, differentiates the vibe. The personalities of the staff make the hotel what Teresa Lake, a Virgin Atlantic executive who has been visiting since childhood, called the most “Jamaican” place on the island. It is, moreover – like its sister historic property in Montego Bay – in irreproachable physical condition. And Jamaica Inn has a secret weapon: its cuisine. Maurice Henry, the former sous-chef overseeing the kitchen, has the gift of being able to extract maximum flavor from everything by doing just enough. If the beach, the ministrations of the barmen, and the intriguing company don’t inspire romance, Henry’s jambalaya or curried goat will bring your senses to life.
Round Hill and Jamaica Inn: vintage resorts, each with its own style, both reinvented for a new century – and still infused with pre-brand, old-school Caribbean hospitality.
Visit
www.roundhill.com &
www.jamaicainn.com
for more information


































