Paradise Found​​​
Bougainvillea, palm trees and a view of the Caribbean Sea frame the pool and patio at Round Hill Hotel and Villas, in Jamaica

A mainstay of the global glitterati, Jamaica’s Round Hill resort celebrates 60 years

he humid air is spiked with the scents of tropical flowers and saltwater. The sun shines onto pristine white sand while sounds of birds cawing in the palm branches punctuate the laughter of guests lounging on the beach below. A glamorous Grace Kelly relaxes in the shade of an umbrella while Truman Capote chats with his old friends Babe and Bill Paley (of the CBS empire) on the sprawling lawn of their villa. Women gossip about what they’ll be wearing to the event of the season, appropriately named the Sugar Cane Ball. Paradise? Absolutely.

Round Hill, the ne plus ultra of Jamaican resorts for the international jet set, has boasted much the same scenery and soundtrack for the past six decades and continues to inspire—as it did Ralph Lauren, who evoked the island hideaway in his Resort 2014 men’s Black Label collection.

An aerial view of the resort shows its size and position on the peninsula’s lush western slope

 

Round Hill’s reputation dates back to even before ground was broken on the lush property in the early 1950s. Once upon a time—when Jamaica was a British colony quickly evolving into a resort destination—a well-connected entrepreneur named John Pringle had a vision: to bring the boutique-hotel model into a new domain by developing a luxury complex where the very rich could own cottages and share profits. As Pringle explained in an essay written for Round Hill’s eponymous coffee-table book, “I wanted my hotel to be unique and its clientele even more so.”

Noël Coward once famously entertained friends by singing at the bar accompanied by Cole Porter on the piano. Oscar Hammerstein wrote the lyrics to The Sound of Music in Villa 12.

Pringle chose to situate his gem on a 100-acre peninsula west of Montego Bay that once housed a sugar plantation. The verdant land also harbored a pineapple grove—the inspiration behind Round Hill’s signature logo. With its architecture conceived by William Ballard, an industry luminary of the time, and chic décor designed by Guy Roop, Round Hill opened in 1953, a complex of cottages surrounding a spacious hotel. Noël Coward, a legendary British playwright, was the resort’s first shareholder. Other high-society visitors, such as Fred Astaire, Vere Harmsworth (of the Daily Mail newspaper fortune) and John and Jacqueline Kennedy, quickly followed. To put it lightly, Pringle’s idea was a smashing success.

 
Many of Round Hill’s interior spaces are decorated in a soothing palette of black, blue and cream tones that offset the riot of tropical colors outdoors 
Many of Round Hill’s interior spaces are decorated in a soothing palette of black, blue and cream tones that offset the riot of tropical colors outdoors 
Many of Round Hill’s interior spaces are decorated in a soothing palette of black, blue and cream tones that offset the riot of tropical colors outdoors 
 
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Throughout the 1950s and on through the ’70s—the height of the jet-set era—Round Hill enjoyed the status of being the crème de la crème of posh playgrounds. Its spacious, open wood-paneled bar is lined with black-and-white photos of smiling guests—a testimony to the legends who sunbathed in Round Hill’s poolside chairs and caroused on its secluded grounds. Coward once famously entertained friends by singing at the bar accompanied by Cole Porter on the piano. Oscar Hammerstein wrote the lyrics to The Sound of Music in Villa 12. Photographer Richard Avedon, Bing Crosby, Alfred Hitchcock and Hedy Lamarr were guests on many a balmy night. Famed society photographer Slim Aarons, a regular visitor, documented the leisurely lives of his wealthy friends, especially C.Z. Guest and the aforementioned Mrs. Paley. To explain the reason the property’s charm was so irresistible during the time, managing director Josef Forstmayr says, “Round Hill established a very strong Jamaican vacation experience with the highest standards of service, cuisine and accommodation while always maintaining a strong local flavor.”

Modern-day Round Hill, boasting 27 villas and 36 hotel rooms, has not changed much; relics from the mythic resort’s storied past are everywhere, balancing out its 21st-century advancements. The hotel’s guest list continues to read like a social register, but Charlie Chaplin, Clark Gable, Princess Margaret and Prince Sadruddin Aga Khan merely have been replaced by today’s pop stars, Hollywood legends, business tycoons, heirs, heiresses and occasional members of royal families. Current shareholders include MTV founder Robert Pittman and Mr. Lauren, who redesigned the main Pineapple House in a classic tropical style and whose two cottages are dubbed High Rock and White Orchid. The latter, formerly known as Cottage 26, famously once belonged to the Paleys. In his 40th anniversary monograph, Mr. Lauren writes of first visiting Jamaica: “We came there on holiday as a young family almost three decades ago, and it wasn’t long before we moved into a romantic old villa overlooking the Caribbean. It had an English colonial spirit and glamour…. It was surrounded by a jungle of trees and flowers, peace and privacy. It was our own Garden of Eden.”

 
Ralph Lauren has owned property at the resort for more than two decades 
Since opening in 1953, Round Hill has been popular with many renowned photographers as a location for fashion shoots 
Such celebrities as Paul Newman and his wife, Joanne Woodward [left], and politicians like John F. Kennedy [far right] were frequent visitors 
 
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And of course paradise wouldn’t be complete without an extravagant fete. The most important happening of the year at Round Hill, the Sugar Cane Ball, is undeniably the most significant proof that old-world glamour and elegance are still alive and well. Held every February on the resort’s Seaside Terrace, the gala raises funds for Hanover Charities, western Jamaica’s largest charitable organization. Founded in 1957, the charity helps to improve education and health services for the residents of Hanover Parish. Attendees over the years have included the governor-general of Jamaica (the representative of Queen Elizabeth II), Ivana Trump and Prince Michael of Kent, who will be an honored guest at the 2014 ball, which is slated to take place on February 15. Throughout a night spent dancing, drinking and socializing, patrons also raise funds through an art exhibition, raffles and a silent auction, which has raised more than US$2 million since 2003.

“The first Sugar Cane Ball was in the 1960s. We have doubled the amount of attendees since then, and special themes—which began back in the 1980s—make it a lot of fun,” says Katrin Casserly, chair of Hanover Charities. Indeed, the ball’s diverse past themes have run the gamut from Venetian Masquerade to Night at the Raj, Chinese New Year: Year of the Dog, James Bond and Studio 54 (the theme of the 2013 ball). The theme for 2014, Black and White, is in homage to Capote’s legendary masquerade ball, an event fittingly as glamorous as the Sugar Cane Ball. Held in 1966, Capote’s masked gala was the quintessence of luxurious splendor, and anyone who was someone was seen that night capering and cavorting in the ballroom of the Plaza Hotel, in New York City. Perhaps there’s no better way to honor that kind of legacy than during a lavish gala on a breezy night at Round Hill.

The Sugar Cane Ball will be held on February 15, 2014, at Round Hill. For more information, please visit hanovercharities.com or roundhill.com.

 

Victorine Lamothe is an editor, writer and translator based in New York.

  • Courtesy of Round Hill Hotel and Villas
  • Courtesy of Round Hill Hotel and Villas
  • Courtesy of Round Hill Hotel and Villas
  • Photo by Bruce Weber; courtesy of Ralph Lauren Corporation
  • Courtesy of Round Hill Hotel and Villas/The Brandman Agency