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The Caribbean, Ralph Lauren Style

A trip to Round Hill Resort in Montego Bay, Jamaica

Written by Cathy Whitlock

Strolling the pristine grounds of this garden by the seashore, one can almost feel the ghosts of an era gone by, a time when Old Hollywood and politicos sipped martinis with Manhattan socialites and the international elite.


Photo: Courtesy of Round Hill Hotel & Villas
Located in Montego Bay, Jamaica, plantation style elegance meets tropical glamour at the Round Hill Hotel and Villas. 

Nestled on a secluded hillside in Jamaica’s Montego Bay, Round Hill is one of the Caribbean’s most iconic resorts. The 110-acre property turned haven was the brainchild of Jamaica-born entrepreneur John Pringle (who first came up with the business model of offering boutique hotel style villas to shareholders in 1953) and it quickly became a favorite of the rich and famous in the 50s and 60s who favored its old-school glam, secluded beaches, scenic villas and above all, its privacy.


Photo: Courtesy of Round Hill Hotel & Villas
Round Hill has 27 individually owned villas. Shown here is the living room of a Ralph Lauren inspired luxury suite, many with vaulted ceilings, large louvered ceilings and infinity edge pools. 

Steeped in tradition, history and lore, the resort’s 27 villas hosted many the illustrious guest. Villa 3 was frequented by playwright Sir Noel Coward and author Ian Fleming, the British novelist who loved the island so much that it inspired the birth of his character James Bond. Composer Oscar Hammerstein met Maria von Trapp at Round Hill and wrote the Sound of Music in Villa 12.


Photo: Courtesy of Round Hill Hotel & Villas
Mahogany and wicker settees become sophisticated island swings on one of the villa verandas.

Book the four bedroom Villa 10 where a young John F. Kennedy and his bride Jackie enjoyed the views and privacy or Villa 25 where the future president edited and rehearsed his famous 1960 inaugural address (“Ask not what your country can do for you”) and perhaps you too will become inspired. And movie buffs will no doubt recognize the stunning Villa 11 where Angela Bassett’s Stella Got Her Groove Back. Co-star Taye Diggs became such a fan that he returned to the resort to marry Idina Menzel in an evening ceremony. Alfred Hitchcock, Bing Crosby, Clark Gable, Bob Hope, Truman Capote, and Paul Newman were also regular guests.


Photo: Courtesy of Round Hill Hotel & Villas
Caribbean living at its finest: A modern plantation style bathroom epitomizes indoor-outdoor living. 

New Hollywood also appreciates the resort’s quiet elegance and charming plantation house charm that is devoid of prying eyes and cameras. Paul McCartney and his family, Meryl Streep and husband Don Gummer, Kurt Russell and Goldie Hawn, Kendrick Lamar, Future, Anna Wintour, Ewan McGregor, Russell Simmons, and Michael Kors are just a few of the celebs who come to chill. On a mission to experience some local flavor in Kingston and attend a Passa Passa (local dancehall reggae event), Ryan Gosling stayed at the resort shortly after filming Crazy Stupid Love. Before acceptance of her Best Supporting Actress Oscar in 2013 for 12 Years a Slave, Lupita Nyong’o (at the suggestion of Round Hill regular Alfre Woodard) stayed at the resort’s oceanfront guestroom and was seen weaving baskets on the property with the locals who come to sell their wares. As Managing Director Josef Forstmayr passionately notes,  “Jamaica brings out the best in everyone and its provenance and history sets it apart from any other place. Families here can be themselves and it’s very low key. Less is more here. And no paparazzi!”


Photo: Courtesy of Round Hill Hotel & Villas
Images of celebrity guests from Paul McCartney to Pierce Brosnan dot the walls of the cocktail bar. 

Credit some of Round Hill’s success and ambiance to Ralph Lauren, who with wife Ricky, fell in love with Jamaica some twenty years ago and purchased both a beach house (purchased from the late CBS head Bill Paley and his style icon wife Babe in 1985) and cottage on the property. Lauren’s design aesthetic is literally felt everywhere as he decorated the 36 guestrooms overlooking a private bay in the resort’s Pineapple House.


Photo: Courtesy of Round Hill Hotel & Villas
Signature blue and white accents are classic elements in this oceanfront room designed by Ralph Lauren.

White stone floors, four poster bamboo beds draped in white netting, signature blue and white accents and upholstered furniture and desks are classic vintage Ralph elements that translate as all-white tropical beach living.  


Photo: Courtesy of Round Hill Hotel & Villas
Classic Ralph: The Pineapple House boasts a vibrant blue and white décor.

Much like the designer himself, Forstmayr explains, “It’s quintessential Jamaican style and just like an exquisite cashmere sweater!”


Photo: Courtesy of Round Hill Hotel & Villas
A pair of mahogany four-poster bamboo beds are contrasted by the vibrant all- white tile flooring, bedding and canopy netting in Lauren’s designs for an oceanfront room

If you want to experience the laid-back plantation style with an updated Caribbean vibe for yourself, call early—Beyoncé and Jay-Z tried to book for Christmas only to find there is no room at the inn.