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A Round Hill Reverie (post by Reggie Darling)

The below post was written by a dear guest of Round Hill, who visited us this past October. We wanted to share his story with you, so please enjoy! You may visit his blog here:

Now that the madness of the Christmas season is over, Dear Reader, I’m planning on posting a series of essays that have been in my queue for some time.  Today’s post, a review of one of the Caribbean’s most storied resorts, is the first in the line up.

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.

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.

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.

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.

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.

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.

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.

Mr. Clark Gable and Mrs. John Pringle at Round Hill
Image courtesy of same

Clark Gable was also an habitué of Round Hill.

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.

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.

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.

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

. . . the pillows in the villa’s indoor living room were perfect, at least for the requirements of Boy, the Fancy New York Decorator.

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.

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.

So, who needs a Speedo?

Bathing suits were largely superfluous, we found.

One does, of course need white wine!

Wine and cocktails, snacks, and meals were but a phone call away . . .

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

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