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Ian Keown’s Caribbean: 60 Years of Caribbean Posh at Round Hill

Noel Coward with Sean Connery in Jamaica during the filming of "Dr. No," the first James Bond movie.
Sean Connery with Noel Coward in Jamaica during the filming of “Dr. No,” the first James Bond movie.

by Ian Keown

“Noel Coward patted me on the knee and said ’Dear boy, if only you’ll stop going on about your damned cottages, I’ll buy one of them‘.”

The Honorable John Pringle, OJ, CBE, a courtly octogenarian with a properly plum-y English accent, was recalling his encounter with the famed playwright/songwriter on a PanAm flight to New York in 1950.  Pringle was the visionary who conceived and created the legendary Round Hill Hotel, 15 miles east of Montego Bay in Jamaica.  A mere 26 years old and following wildly contrasting stints as equerry to the Duke of Windsor and top salesman for Estee Lauder, he had no experience of running hotels; yet he is generally considered to be the father of tourism in Jamaica and, by extension, one of the most influential pioneers of tourism throughout the Caribbean.

“I had this idea about a colony of luxury cottages,” Pringle told me shortly before his death in 2007.  “I would sell them to wealthy people who would stay there in winter, then rent them out as hotel rooms in summer.  I knew the type of people I wanted — mummy’s friends.”

Interior at Round Hill, Jamaica
Interior at Round Hill, Jamaica

His mother’s friends just happened to be the cream of the crop of London society (Pringle’s godfather was the Duke of Sutherland).  When he had found his dream site — 28 acres of a secluded whaleback promontory on Jamaica’s northwest shore, then a coconut and pineapple plantation — and put his proposal on paper Pringle set off for New York and found himself sitting next to the celebrated  playwright/songwriter.  Coward did indeed buy the first cottage but then a few days later introduced Pringle to his friend Adele Astaire (Fred’s sister), who also bought one.  Before Pringle had even flown off to London to pester mummy’s friends, he had sold half of Round Hill’s cottages and one of the world’s most celebrated resorts was off and running, something of a legend right from the start.

This was a stroke of luck not only for John Pringle but for Jamaica (and the Caribbean): his vision for Round Hill defined a clientele that any island would envy (there were exceptions — “I once had to order Rex Harrison out of my hotel,” Pringle told me, “for behaving abominably to one of my staff“) and set a tone of refinement that places it in the pantheon of storied caravanserais like, say, Hotel du Cap on the French Riviera or the Cipriani in Venice.  This year, Round Hill Hotel & Villas is celebrating its 60th anniversary as one of the world’s legendary resorts, a newsworthy achievement at a time when new hotels zoom into the blogosphere and then fizzle and fade before your next vacation comes around.  Designed for the long haul, Pringle’s revolutionary business plan is quite commonplace today: cottage owners could recoup their investment by making their villas (or individual suites) available for rentals eight months of the year to lesser mortals while they themselves returned every winter with bulging wallets.  And return they did: the Aga Khan (who adopted the Pringle formula when planning his own luxury resorts in Sardinia back in the 80’s); a London newspaper mogul; an Italian count whose ancestors crop up in grand operas; John and Jackie Kennedy (who spent part of their honeymoon there); Cole Porter and Leonard Bernstein (who often played the Steinway for their fellow guests).  One longtime owner told me of the evening the local mento band played some of Bing Crosby’s hit songs and the crooner was so delighted he slipped them a tip so lavish they immediately packed up their bamboo flutes and rhumba boxes and disappeared for a whole week.

Bedroom at Round Hill
Bedroom at Round Hill

That was then, of course, how about now?  Well, how about Paul McCartney, Diane Sawyer, Ewan McGregor, Michelle Williams, Russell Simmons and Steve Case of AOL fame?  They’ve all vacationed at Round Hill in recent years.  Ralph Lauren owns a “beach cottage” in the resort to augment his grander villa just up the hill.   And three years ago my family and I were mesmerized by the contortions of Meet the Press’s David Gregory trying to maneuver his 6-foot-5-inch frame under a floor-hugging bar while dancing the limbo.

Round Hill, Jamaica from the air
Round Hill, Jamaica from the air

At first glance, from the top of the flower-lined driveway leading down to the green-striped awnings and shingled roof of the clubhouse, Round Hill looks less like a resort than a large hillside garden planted with cottages rather than the other way round — 27 cottages gift-wrapped in flowering shrubs and bougainvillea vines, all of them overlooking a broad bay and sandy cove.  What Pringle referred to as “cottages” modern usage would call “villas,” ranging in size from two bedrooms to six bedrooms.  They are designed for sublime privacy and unabashed lazing, with lots of jalousie windows and ceiling fans for steady breezes (bedrooms are air-conditioned), a plush “outdoor” living room, a spacious deck with a private pool and a small kitchen where private maids prepare breakfasts to order.   It was a masterful design from the beginning and people looking for an escape from the 21st century still applaud its Caribbean Classic features.

In 1989, the cottage owners had the foresight to acquire a young Austrian, Josef Forstmayr, as Managing Director.  He’s still there, now one of the most respected hoteliers in the Caribbean.  I first met Forstmayr at another hotel on Jamaica not long after he arrived on the island in 1979 and was instantly impressed by his innate professionalism and his ability to make everyone, guests and staff, feel part of a select band of discriminating travelers.  A graduate of the University of Salzburg who greets his guests in effortless English, Italian, French and German, Forstmayr is the very model of an Austrian hotelier but with the customary pinstripes and cufflinks displaced by modish slacks and tropical togs.  He is totally committed to Round Hill’s mystique and traditions (this is, above all, a place where they cherish continuity) but he has diplomatically nudged the owners, the diehards versus the faddists, into the 21st century without sacrificing Round Hill’s Caribbean soul.   The original cottages, for example, were furnished with what might be called Safari Camp Chic (iron bed heads and banana-trash lampshades — the “luxury” came from the setting and the enveloping serenity) but they have now acquired a modestly contemporary vibe, although even today only a few of the suites have TV sets, which are usually tucked into armoires.

The Round Hill look
The Round Hill look

Having stayed at Round Hill on and off for almost 40 years, I’m not always thrilled by some of these trends — the live music on weekends is sometimes over-amped (harrumph!) and occasionally I’ve spotted dinner guests in shorts (double harrumph!) — but I am always impressed by the easy rapport between guests and staff.   Most of the maids, waiters and gardeners are following in the footsteps of fathers, aunts and cousins who often served the same guests.  Their village churches and charities thrive on donations from Round Hill regulars.


JFK at Round Hill
JFK at Round Hill


Sixty years on, Round Hill still fulfills John Pringle’s original promise: a refined setting for refined people seeking privacy but with plenty of options for mingling when you feel the urge to hobnob with fellow guests — over afternoon tea at the beachside terrace, at the manager’s weekly cocktail party for guests and owners, or playing doubles on the tree-shaded tennis courts.

The hotel’s delicately phrased invitation to players on the five, lighted courts sort of sums up Round Hill’s guiding philosophy: “We pride ourselves on presenting the game as it was intended:  as a genial game between gentlemen and ladies.  Proper tennis attire (white preferred), including tennis shoes, must be worn at all times… “

Mummy’s friends would expect nothing less.


Round Hill Hotel & Villas, near Montego Bay, Jamaica: 27 villas (84 suites), 36 luxury rooms in Pineapple House; special 60th anniversary offer from $379 double; www.roundhill.com, 800/972-2159.


iankeown-150x150    Ian Keown is a freelance writer based in New York City. Over the past 30-odd years his byline has appeared inTravel & Leisure (as a contributing editor), Gourmet (as contributing editor), Caribbean Travel & Life (contributing writer),  Diversion (as contributing columnist), Departures, ForbesFYI, San Francisco Examiner, Worth and Opera. His guidebooks include his own series of lovers’ guides: Guide to France for Loving Couples, Very Special Places: A Lover’s Guide to America, European Hideaways and Caribbean Hideaways (which the Miami Herald called “the bible.”).   He is the recipient of the  Marcia Vickery Award for Travel Writing and the first Anguilla 40 Award for in Recognition of Outstanding Contributions to Anguilla Tourism.

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  1. September 19, 2013 at 11:52 pm — Reply

    Great writer, great article, got to know more on Caribbean, will try to visit the place

  2. Everton
    September 20, 2013 at 5:59 pm — Reply

    love your article. I have spent time at Round Hill and it is absolutely fabulous, I love it. I am Jamaican and I have been to many hotels all over the island and my favorite by far is Round Hill. The architecture, the setting, the staff absolutely amazing.

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