By Alexander Britell

In the winter of 1960, then-president-elect John Fitzgerald Kennedy was looking for a getaway before the tempest of White House life began in earnest a month later.

He settled on Round Hill, already a jet-set favorite after opening its doors in Jamaica in 1953,  a place that offered the kind of tranquility – and privacy – JFK sought. (JFK had also spent a vacation at Round Hill a few years earlier).

It was here that the newly-elected president set to practicing his now iconic speech: “Ask not what your country can do for you – ask what you can do for your country.”

JFK, who was vacationing with his wife Jackie, stayed in the then-two-bedroom villa called Cottage 25, set near the base of the hotel’s namesake hill with sparkling views of the Atlantic. (The villa had originally been owned by Adele Astaire).

While Round Hill offers 36 hotel rooms, its collection of 27 luxurious villas have always offered the pinnacle of Caribbean luxury, rarefied, secluded, elegant retreats with all the amenities of the hotel and the space of your own private home.

Cottage 25 is no exception.

Now boasting three bedrooms, it’s a stunner, with a sweeping pool and hot tub, a lush hillside garden and a host of secluded corners for afternoon naps. (The garden is perhaps the most beautiful feature of a villa that doesn’t lack for highlights).

The inside is exquisite with rich wood, massive bathrooms and an impressive collection of Caribbean art.

Every cottage at Round Hill has its own team — they are the full fledged stewards of the property, often staying with a single unit for decades.

Cottage 25 is home to Joy Murray Marston and Verona Grubb, warm, kind and utterly attentive.

They’re the ones who will prepare your breakfast on the patio each morning, clean the villa and handle any request.

They’re joined by Nerrod Fletcher, who keeps the grounds and the pool looking just so.

Verona Grubb and Joy Murray Marston.

As the days go by, the Round Hill villa life becomes intoxicating. The beauty brightens, the palm leaves get greener, the sunsets bolder. Some days you don’t even descend the hill at all.

If it seems like every need you can think of is taken care of, its because it is. There isn’t service like this elsewhere in the Caribbean, where just about everyone you meet knows what you’re doing that day, what you need, what you’re looking for, from Joy and Verona to any of the bellmen to, of course, legendary concierge Kingsley Blake.

The marvelous garden at Cottage 25.

It gets to the point where all you have to do is think about something and it gets taken care of.

If JFK had stayed here any longer, he might have changed the introduction to his speech.

“Ask not for anything at all.”

See more in the latest CJ video at the top of the page. 

For more, visit Round Hill.