A long-standing icon in Jamaica, Round Hill’s roots are rich with history. Originally, the 100-acre peninsula was part of Lord Monson's Round Hill Estate – a sugarcane plantation that later grew coconuts and pimento (allspice). The peninsular bluff’s fertile soil and ideal climate was also home to pineapple groves, which became forever prominent in the Round Hill logo and can be found sprinkled throughout the property.
Round Hill was conceived by Jamaica-born entrepreneur John Pringle, whose vision was to take the 'boutique' concept both onto another level and into a new domain. John was raised with hospitality in his veins, as his mother owned the former Sunset Lodge Hotel in Montego Bay and was a prominent social figure in Jamaica. After John completed schooling and served in the British Army, he spent a few years in New York City where he worked for Elizabeth Arden and ultimately left to open his own men’s fashion boutique. After meeting his wife and starting a family, John wished to return to Jamaica with his family to put his ambition and talents to work.
The plan for Round Hill resort in Montego Bay comprised the design and development of a luxury cottage complex that, based on John's revolutionary business model, would offer those who purchased a cottage a share in hotel profits. In other words, he envisioned creating a unique Montego Bay resort that would appeal to the very rich who desired a cottage in the West Indies without the concern of absentee ownership.
John worked tirelessly to turn his dream into reality, and in 1953, Round Hill opened its doors to great acclaim with Sir Noel Coward as its first shareholder. Prominent American and European socialites, literati and artists were invited to build 'cottages' and invest in the hotel. Shareholders included Adele Astaire, Bill and Babe Paley, Lord and Lady Ednam, Mr. and Mrs. Oscar Hammerstein, Clive Brook, Jack and Natasha Wilson, the Marchioness of Dufferin and Ava, Mr. and Mrs. Henry Tiarks and Viscount and Viscountess Rothermere.
The original architecture was designed by William Ballard and the décor was conceived by Guy Roop. Collaborating with Mr. Pringle, they brought to fruition a collection of impeccably designed, freestanding, whitewashed cottages that capitalized on the incredible views of the bay and warm, Caribbean climate. This 'cottage colony' model that Pringle had devised at 26 years old has since been widely copied by others all over the world.
Over the past sixty years, Round Hill resort in Montego Bay has maintained its secluded ambiance and classic charm while building upon John’s original vision. Many of the cottages today have been fully upgraded and expanded, include modern fixtures and amenities, and boast the latest technology while still maintaining the authenticity that they were built upon. The Spa at Round Hill and surrounding grounds were acquired in 2001, adding 10 additional beachfront acres to the property including a beautifully restored 18th century plantation house.
Today, the inspired capacities of Round Hill’s Managing Director, Josef Forstmayr, and team of highly skilled and dedicated staff have been able to preserve the history and legacy of this iconic resort while staying at the forefront of the current industry.
Take a peek into the wood-paneled bar in Round Hill’s lounge and you will find an array of black and white photographs of times past – depicting the carefree, whimsical and chic, laid-back style that has defined Round Hill over all these years.
Read More about John Pringle
Pineapple House’s 36 deluxe guestrooms were redesigned under the careful direction of Ralph Lauren.
Sir Noel Coward, Errol Flynn and Ian Fleming were known to holiday in Jamaica quite often.
Viscount Esmond Rothermere ("Daily Mail" newspaper fortune) was the original owner of Cottage 16 at Round Hill with Lady Anne Rothermere, his wife.
In this villa, history tells us that Ian Fleming's 'good friend' Lady Rothermere heated up their relationship until Noel Coward and Ian decided to move down the coast to Orecabessa to start a property similar to Round Hill.
This property was owned by one of their Jamaican friends - Blanche Blackwell. Blanche wanted to develop a similar resort there. Blanche's son, Chris Blackwell, is continuing this dream with the recent opening of Goldeneye in Orecabessa.
Errol Flynn actually bought Navy Island in Port Antonio, another 2 hours drive east of Orecabessa. His widow Patrice Wymore-Flynn still operates her cattle farm there.
John F. Kennedy and Jackie Kennedy preferred to stay in this four-bedroom villa with pool because of its privacy, magnificent view and large lawn, great for entertaining and children's play. In fact, JFK and Jackie Kennedy honeymooned in this villa.
This spectacular cottage was the setting for the big screen picture by 20th Century Fox, "How Stella Got Her Groove Back," starring Angela Bassett, Taye Diggs and Whoopie Goldberg. Taye Diggs later returned to Round Hill to marry the famous actress Idina Menzel.
Many musicals have been written in this cottage by the original owner Oscar Hammerstein. History tells us that it is at Round Hill where he met Maria von Trapp and "The Sound of Music" was written.
This villa was originally owned by dancer and entertainer, Adele Astaire. Later, John F. Kennedy edited and rehearsed his now infamous inauguration speech by the pool. You can view several artifacts of his stay and speech in the villa today.