Learning To Relax: Round Hill, Jamaica

I am a city girl. When taking online quizzes like, “which country should you travel to next?” or “what’s your travel style?” I always end up with some sort of cosmopolitan destination. I love walking aimlessly through city streets, trying all the food, and- of course- people watching. Always on the go. 

But I’m learning how to relax.

It’s a funny concept: learning to relax. Relaxing seems like something that should come naturally, an ability that we’re inherently born with like breathing. But for most people relaxing is hard! There are thousands of books, apps, workshops, and guided meditations yet still most people would say they struggle in this area.

Round HIll Pool.JPG

I had the opportunity to visit Round Hill Hotel and Villas, located in Montego Bay Jamaica, for three nights at the end of October. It’s not a big secret that a good travel companion is worth their weight in gold and can make or break a vacation, so when none of my trusted travel companions could make the trip, I decided to go solo. I’ve traveled on my own before but never for this long and only to cities, never to a resort. Would I feel lonely? Bored? Would all the honeymooners make me depressed and miss my boyfriend at home? I had no idea. But what I did know is that working on the beach would be far superior to my windowless cubicle.

Round HIll Departure.JPG

The flight from New York to Montego Bay is surprisingly short and fabulously direct. Round Hill is just a half hour cab ride from the airport so you can easily go from grabbing breakfast at the airport to savoring lunch overlooking the ocean, cold beer in hand.

Round Hill Villas.JPG

Built on a sugar-turned-pineapple plantation, Round Hill Hotel and Villas is a historical boutique hotel comprised of 36 beachfront rooms and 27 villas. Designed by Ralph Lauren, the rooms are traditional but airy- exactly the blue and white preppy that you would expect. The villas, on the other hand, are all privately owned and individually designed, though they incorporate Lauren’s stylistic vision. Some villas have private pools. Those that do not are close to the resort’s pools and have oversized terraces and lawns. The villas range from 2 to 5 bedrooms, making them perfect for families. Each of the bedrooms has an individual entrance so they can also be sold as separate rooms. The villas come allocated with 3 private staff members, including one that can cook breakfast.

Round HIll Villa Pool.JPG

Ralph Lauren himself owns two of the villas, which are not available for guests to stay in unless he is on property. He’s not the only famous name who has frequented the property; Prince Harry was recently best man in a wedding and it was rumored Paul McCartney was visiting during my stay. The cocktail bar is full of photos of the resort’s many famous guests. John F Kennedy even wrote his inauguration speech in villa 25.

Round Hill Villa Table.JPG

None of the rooms in either the hotel or villas have televisions. You must be thinking; a single girl goes to a resort on her own with no TVs! She must be SO BORED! The absence of television was a conscious choice by the hotel to get guests to truly relax. Should you really need to see the big game, you can head over to the Pineapple room. There’s also a library if you’d like to print your boarding pass.

Though Round Hill is rated the #1 hotel for families in the Caribbean, it’s definitely a family-friendly resort and not a family-centric resort. It’s the perfect place for adults who have kids, but hate other people’s kids. There were no children screaming, running around, or splashing in the pool. In fact, because children spent most of their time in their villa’s pool or the free kids club, I hardly saw children at all. Babysitting services are available for an insanely low rate of $10/hr so parents can enjoy dinner off property if they’d like.

Round HIll Farm.JPG

Being a smaller property, the chef has the opportunity to create quality meals instead of the massed produced buffets typical of an all-inclusive resort. Round Hill created the largest organic garden (of this type of establishment) in Jamaica, the products of which the chefs incorporate into their dishes.

While there are several places to eat throughout the day, dinner is hosted at only one location per night. Twice a week dinner is served in the farm-to-table fine dining pavilion, other nights it’s served on the more casual seaside terrace or as a beach bbq, complete with music, dancing and bon fires!

Round HIll restaurant.JPG

Though there aren’t a lot of structured activities, like there are at a traditional resort, I still found plenty of things to do to occupy my time. In addition to the traditional free non-motorized sports, like kayaks and paddle boards, Round Hill offers a daily free glass bottom boat ride. Also complimentary is a shuttle which takes you to the local craft market, Hip Street and downtown Montego Bay.

My days were spent reading or working on the beach or by the pool, or enjoying cocktails at the beach bar. Even when the resort is full, there’s always choice seating available on the beach so you don’t have to rush out at the crack of dawn to throw down a towel. You can also visit the spa or fitness center.

Round Hill Beach.JPG

At four pm it’s time to join the other guests in the cocktail bar for a daily complimentary high tea. Based on the villa concept of the property, one would think that Round Hill is a very private keep-to-yourself resort. And while it certainly can be if you want, most guests are chatty, warm, and eager to meet new people. High tea is just the start of the social activities. The hotel also hosts a cocktail party at the pool bar for guests to mingle and share their newfound knowledge of the island.

Round HIll green.JPG

What makes Round Hill so special are the people that it attracts. Most people I met come annually, giving a sense of family and acceptance. At lunch one day I met a family with three small children from Australia. Each one of their children was born in a different country and we spent hours talking about our lives and the adventures we take. After dinner one night, a wedding group at called me over to enjoy after dinner drinks with them. Suddenly it was 2am! At the cocktail party, I met a Canadian/Swedish couple and a single Greek man. Our conversation spilled from the party to dinner, where we emptied several bottles of wine.

Round Hill is definitely not for everyone. It’s very small; there’s no swim up bar, and definitely no nightclub. It can seem a bit quiet. If you like a lot of scheduled activities, you may be bored. But if you truly just want to relax, can create your own fun, and don’t like overwhelming large hotels, Round Hill is fabulous. It’s not all inclusive, but you are able to charge everything to your room so you don’t have to carry cash. Not having an all-inclusive plan encourages guests to go off property and try local restaurants.

Round HIll Sunset.JPG

It was a truly relaxing experience. I found freedom being on my own schedule with nobody’s needs to look after but my own. I was able to be alone when I want, to be social when I want, and to eat when I want. After four days, I felt like I was walking on a cloud. As I walked through the Montego Bay airport to my gate all the little things that typically annoy me when I fly didn’t faze me in the slightest. While I know that I can’t just escape for 4 days whenever I feel stressed out, the reset definitely put me in a better position to come back and tackle my life and its stressers.


Good for: Families, groups, couples, history buffs, those looking for a quiet, relaxing experience
Not good for: Party lovers, those looking for a lot of onsite activities, those looking for a large resort 
Price point: low season starts at $429/nt, high season starts at $959/nt
Special features: Complimentary glass bottom boat
Amenities that you get booking with me: Daily breakfast for two, $100 food and beverage credit, welcome amenity, and upgrade/early check-in/late check-out upon availability. Guests booking suites for a minimum of two nights also receive a $100 spa credit.

Nayara Springs: Secluded Heaven in the Sky

Do’s and Don’ts of Cuba