This past October Boy and I visited Round Hill in Jamaica, to celebrate a milestone birthday for Boy.
| The Main Lodge at Round Hill |
Round Hill is one of the fabled Caribbean resorts, and one that I've always wanted to visit. This was my first—and I'm confident will not be my last—stay at the Queen of Jamaica's resorts.
Situated on a secluded, 100+ acre peninsula near Montego Bay, Jamaica, Round Hill has virtually nothing in common with the enormous all-inclusive resorts the island is known for. Round Hill is, in contrast, very discreet, quiet, small, and exclusive.
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| An aerial view of Round Hill Image courtesy of same |
Long celebrated for its exquisite location, luxurious amenities, splendid service, and rigid door policies (no tourists allowed, thank you), Round Hill has long been a favored tropical destination for those born with golden spoons in their mouths, captains of industry, international socialites, Wall Street heavyweights, and Hollywood icons of the old school.
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| Babe Paley and her husband, William Paley at their villa in Round Hill, photographed by Slim Aarons |
For example, Mrs. and Mrs. William Paley were once among Round Hill's most famous residents.
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| Mr. and Mrs. Ralph Lauren at Round Hill Image courtesy of Architectural Digest |
Today their villa at Round Hill is owned by Mr. and Mrs. Ralph Lauren.
| The view from the veranda at Round Hill's main lodge |
Round Hill sits on a lovely, sheltered bay, far from the hubbub and madness of Montego Bay.
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| President John F. Kennedy at Round Hill Image courtesy of Round Hill |
President and Mrs. Kennedy were regular visitors at Round Hill, drawn to it for its exclusivity and firm policy of protecting the privacy of its guests.
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| The pools at Round Hill Image courtesy of same |
The resort has all of the amenities that one could possibly wish for: a protected beach, pools, a spa, several bars, luxurious dining pavilions, and more. The staff couldn't be nicer, or more accommodating.
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| Miss Grace Kelly, relaxing on the beach at Round Hill Image courtesy of same |
Grace Kelly was a regular visitor at Round Hill, both before and after her marriage to Prince Ranier of Monaco.
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| Mr. Clark Gable and Mrs. John Pringle at Round Hill Image courtesy of same |
Clark Gable was also an habitué of Round Hill.
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| Miss Mary Martin and Sir Noël Coward at Round Hill Image courtesy of same |
The playwright and composer Sir Noël Coward once owned a villa at Round Hill, where he regularly entertained the stars of Broadway and London's West End.
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| Miss Joanne Woodward and Mr. Paul Newman having fun at Round Hill Image courtesy of same |
Joanne Woodward and her husband Paul Newman were no strangers to Round Hill.
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| Sir Paul McCartney and friends at Round Hill Image courtesy of same |
More recently Sir Paul McCartney and his family have been frequent visitors to Round Hill.
| The villa we stayed in at Round Hill |
While Round Hill's storied history was a plus for us, it was the sybaritic luxury of the resort that attracted us to it.
| A night time view of the villa |
We stayed in a private villa during our visit there, owned by a major U.S. media mogul.
| The outdoor living room at our villa at Round Hill |
The villa was beautifully appointed, with both outdoor and indoor living rooms to lounge about in.
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| The lovely, charming, and sweet Angela, the Major Domo of our villa at Round Hill |
We were beautifully attended to during our stay by a housekeeper/cook, two maids, and a gardner/poolman. The staff cooked breakfast for us at our villa every morning, and served us lunch, too.
| The "English taste" method of arranging pillows |
We found the accommodations pleasant and exceedingly comfortable. After only a minor amount of rearranging . . .
| The "American taste" method of (re) arranging pillows |
| Another view of the pool at our villa at Round Hill |
We hardly left the grounds of our villa during our stay at Round Hill. Why should we, when we were so beautifully attended to? We ate breakfast and lunch at our villa every day, and we only ventured out in the evening for drinks and dinner at the resort's handsome bar and dining pavilion. It was all very cushy, and very private, Dear Reader.
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| Boy swimming in his birthday suit at our villa at Round Hill |
We spent most of our time at Round Hill lazing about our villa and swimming in its private pool.
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| So, who needs a Speedo? |
Bathing suits were largely superfluous, we found.
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| One does, of course need white wine! |
Wine and cocktails, snacks, and meals were but a phone call away . . .
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| The splendid evening sky at Round Hill Image courtesy of same |
It was a lovely, low-key holiday, and a welcome respite from the madness of Manhattan and one's more mundane daily responsibilities. I look forward to returning to Round Hill again sooner rather than later. I highly recommend it to you, Dear Reader, as the perfect getaway from one's winter cares . . .
Round Hill Hotel and Villas
John Pringle Drive
Montego Bay, Jamaica
(800) 972-2159
www.roundhill.com
Please note: Reggie has received nothing in return for writing this review of Round Hill in Jamaica, nor does he expect to. He has written this review solely for the enjoyment of his readers, which is why he writes this blog.
All photographs, except where noted, by Reggie Darling














































