Love Letter

It's All Good at Round Hill

by Anna Watson Carl

Round Hill, a genteel, country club-style beach resort in Jamaica, gets top marks when total relaxation is the only agenda.  

MONTEGO BAY, Jamaica – He had me at hello. Not sure if it was his lilting Jamaican accent, his relaxed demeanor, or the fact that he was offering me an ice-cold rum punch, but I was smitten. Sporting a bright turquoise jacket with shiny brass buttons and an ear-to-ear grin that could have easily been on a Crest White-Strips ad, Kingsley Blake welcomed us to Round Hill.

"Now that you're here, you don't worry about a thing. You are here to relax." Looking out from the open-air lobby to the sweeping veranda, palm-tree dotted lawn, and the expanse of sparkling blue water beyond, it was easy to believe him.

There's something preposterous about taking off from New York on a bitterly cold, gray January morning and arriving, five hours later, on a tropical island that bears no trace of winter. Our squinting eyes were greeted by blinding sunshine, blue skies, and flowering trees, which was equal parts disorienting and marvelous. Our pale, swaddled bodies looked like alien creatures in this world of color and heat.


But our Round Hill welcome put us at ease. We later learned that Kingsley, the hotel's concierge (in his 38th year on staff there!), greets every guest with a smile and a cold drink and personally escorts them to their room. We were more than impressed.

Once the heavy winter layers came off — replaced by swimsuits and flip-flops — we began to unwind. This was my third trip to Jamaica, and I've seen a good deal of the island. I've driven across its pot-holed roads, eaten goat curry from a roadside stand, and tasted jerk chicken so hot it made my blood boil. I've spent time in small villages in the center of the island with not a tourist in sight, cooked with locals, and listened to live reggae into the wee hours. I've also stayed in larger resorts in Negril, in Ocho Rios, and in Montego Bay, and done plenty of sightseeing. But this time, my husband and I had only one agenda: to completely and totally relax.

Round Hill Beach

It would be impossible not to relax at Round Hill, which is far and away one of the most beautiful spots I've ever visited. Sitting on 110 acres of lush jungle-meets-ocean property just 30 minutes outside Montego Bay, Round Hill is nothing like the mega-resorts you find elsewhere in Jamaica. With just 36 hotel rooms and 29 private villas, the property oozes charm, with an old-world elegance carried over from its early days in the 1950s and '60s when jetsetters like Babe Paley, Noel Coward, and the Kennedys (JFK and Jackie) vacationed there.

Each of the guest rooms — all decorated by Ralph Lauren, a property owner at Round Hill, with four-poster mahogany beds and white-on-white décor — boasts an ocean view, and many have French doors that open onto private terraces. The bathrooms, with deep soaking tubs and walk-in showers, are spacious and spotless. Sitting on our terrace, whether drinking coffee early in the morning or watching the sunset with a glass of wine, we felt like we had just been handed a little slice of paradise. Truly perfect. One thing the rooms do not have (happily) is a TV, so take note if you were hoping to catch up on Downton Abbey.

Round Hill balcony

You won't lack for distractions. There's a gorgeous infinity pool surrounded by plush white lounge chairs that seems to spill directly into the ocean below. Though small, the beach is perfect for a sunset stroll or a cocktail at one of the tiki-style bars. The Spa, added in 2002, is housed in a former 18th-century pineapple plantation home surrounded by a manicured lawn that sweeps down to the ocean. They offer all manner of treatments, from massages to facials, plus a little gym and a hair and nail salon. The spa is about a ten-minute walk from the rest of the resort, accessible only by a narrow, winding path along the ocean surrounded by hanging vines and dense foliage. It's absolutely stunning, and a nice excuse to take a leisurely walk. I attended an outdoor yoga class one morning and loved seeing the ocean while doing a downward dog.

Round Hill Bar


Round Hill House

As for the food, it's good, not great, though they grow nearly all their produce on two organic gardens on the property. There are plenty of light, swimsuit-friendly dining options — grilled fish, salads, and grains — and a nice (though pricy) wine list. I love that they serve afternoon tea with scones, sandwiches, and the like. The biggest night of the week (with the best food as well) is Monday, when the whole resort heads to the beach for a huge BBQ. With flowing rum punch, grilled lobster, and a steel drum band, this night is worth planning your trip around. 

We loved our time at Round Hill. As in, I cannot wait to return. After four days of sunny weather, plenty of sleeping, reading, and sunning, we were completely unwound. If a winter (or spring or summer) stress-free getaway is what you're after, Round Hill is the ticket. 


Fly: Sangster International Airport (MBJ) in Montego Bay has direct flights to many US cities. Round Hill is 20 minutes west of the airport. 

Drive: Jamaica is a former English colony, so they drive on the left side of the road. You can rent a car to get around, but Round Hill can arrange drivers if you want to check out a local jerk shack in town. Good to know: The island is deceptively large, and the roads aren't all fantastic. Distances may take longer to cover than you might think. 


Round Hill Hotel and Villas
John Pringle Drive, P. O. Box 64
Montego Bay, Jamaica


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