Round Hill Resort – Jamaica’s Timeless Beauty

Round Hill Resort – Jamaica’s Timeless Beauty

It’s that time of year again when I get that itch for warm sun on my face, tanned feet, coconut infused cocktails and salty kisses. March has always been my favorite month for Caribbean travel, as it is the time when I start to get a little cabin fever and am ready to say good-bye to my beloved New England winter.


When searching for an ideal Caribbean destination for travel with our then infant daughter, Pippa, I was looking for several key things: a non-stop flight (from New York or Boston), a resort not too far from the airport, luxe hotel accommodations, kid friendly and of course high quality food and a beautiful beachfront. Not too hard, right?  Our preference has always been those of lower key, smaller luxury properties versus some of the larger commercialized resorts. I surveyed many and while the feedback often geared us towards the bigger kid friendly choices, I knew those properties were not a fit for us.  After weeks of my own research I knew I had found my spot when I came across Round Hill Resort in Jamaica.  Rich in history and tradition, Round Hill appeared to be a classic, chic smaller property. They also boasted about their kids program and farm to table cuisine right from their own gardens.  Oh, and did I mention Ralph Lauren owns a villa here and also responsible for most of the design in the newer boutique hotel portion? It instantly checked off all the boxes.  

It had been over ten years since my last trip to Jamaica but I recalled how much I loved the culture, the warmth of the people and especially the  flavors of the local cuisine.  If anything ‘jerk’ was on the menu, I would load up!  After seeing all that Round Hill had to offer, it was an easy decision that this would be our mid-winter destination.  I was looking very forward to getting back to Jamaica and sharing it with Matt, who had never been and our new daughter, Pippa.

The flight into Sangster International Airport, Montego Bay from the East Coast is a easy one, four hours from the NYC airports and around four and a half from Boston Logan.  Upon arrival into Montego Bay, we were met by the loveliest woman from  MOBAY, Jamaica’s personalized airport meet and greet service.  This was the best $160 spent for the two of us.  The courteous representative met us as we disembarked and fast tracked us through a private customs and immigration process.  I knew I would receive no complaints from my husband on this when we saw the lines to go through the customs and immigration.  Please take note…arriving and departing the island on a Saturday can be a nightmare if you do not opt for this.   I highly recommend doing this no matter when you travel.  It also grants you access to the MOBAY VIP lounges as well, which came in very handy on our departure.

The twenty minute drive from the airport to the resort takes you through the heart of Montego Bay.  As we made our way along the scenic winding road, I already liked how removed I felt from the hustle and bustle of the tourist scene in Montego Bay.  


Pulling into Round Hill for the first time I knew this was the right choice for us. Greeted at the security gate and led into the property, Round Hill Resort sits amongst 110 acres of lush tropical flowers and gardens on its own private peninsula. With breathtaking views from nearly everywhere I looked I was thrilled that this is where we chose to spend our family vacation.

As we reached the main building with its iconic green and white striped canopies, we were met by the very friendly staff and their signature rum punches.  

From the old-fashioned mahogany counter check-in, to the black and white checkered tile flooring, the open air lobby lounge has a very British Colonial feel with a modern and tropical twist.

Round Hill Resort is a classic beauty, full of relaxed timeless elegance. What drew me to Round Hill in the first place was this understated luxurious vibe.  

Once a pineapple plantation, there is natural beauty in every corner of the resort. 

Round Hill first opened its doors in 1953 and has been a favorite escape for its guests ever since. From celebrities, to politicians to even recently the Royals (Yes, Prince Harry and Megan Markle spent the weekend there ahead of us two years ago). John and Jackie Kennedy favored Villa 10 for their family vacations and other of its famous guests included Grace Kelly, Adel Astaire to just name a few.  Perhaps most notable, Ralph Lauren and his family own a villa right at Round Hill and has been a favorite family vacation spot of his for years. One will see Ralph’s footprint quite a bit throughout the resort.


Guests have two options when planning a trip to Round Hill:  The Pineapple House, which is the boutique oceanfront hotel or a choice of one of the 27 villas that are set up on the hill.  

The first year we went with Pippa, who was 8 months old at the time, we opted for the hotel.  I loved the Pineapple House!  For me, being closer to the water is always better!  The boutique hotel boasts 36 Ralph Lauren designed rooms.  We had an oceanfront balcony room, featuring a separate seating area and king-sized bed.  The sunset views from our terrace were something else.  The set up worked well with an infant as it was easy enough to make trips back and forth to the room from the beach, pool and restaurants.  The Pineapple House is just steps from the infinity pool, which also has a shallow kid pool.  The décor is minimally perfect, decorated in whites with hints of tropical blue. Each guest room features upscale modern amenities. 

This past year we were fortunate to be able to stay in one of their private Villas.  There are 27 unique, private villas, most with their own swimming pools. The villas come with a delightful on-site staff, who are available to prepare daily breakfast and other meals if you should choose.  The villas are situated amongst the hill lending to some of the most majestic views of the Jamaican seaside.   

The villas are ideal if you are traveling with family or a group of friends.  As Pippa was nearly two this time around, the villa worked better for us as we like having a separate bedroom when we put her down to sleep. Our villa was splendid.  We truly enjoyed the privacy that came along with the villa.  Being able to eat in our outdoor dining area at night after we put Pippa to bed couldn’t have been more convenient. 

*There are private villas and there are also split villas. The split villas may share a common outdoor area, pool and even a kitchen. This would be great with another family or group you choose to travel with.  I personally would not opt for one of these as you do not know who will be on the other side.

Round Hill is quiet and relaxed. That is the one thing perhaps that stood out to me the most about Round Hill versus other places we have stayed in the Caribbean.  The resort could be fully committed and you never would know.  The privacy and lack of crowds was huge for us. I never felt we had to ‘lobby’ for a pool chair or get to the beach before breakfast to drop belongings (which is a pet peeve of mine), no swim up bars and rowdy pool parties. This is not a spring break spot.  Even when we stayed at the Pineapple House and would spend late afternoons at the Infinity Pool, we were often only there with a handful of others.  A visit to Round Hill for me is all about the relaxation, privacy, the beauty and above all the best service we have received at a Caribbean property.  

The service at Round Hill is extremely personalized and top notch.  The staff, most of all who have been with the property for decades, will refer to you by name and by the end of your stay you will be sad to say goodbye. There is something to be said when returning to a beloved spot you are greeted by the same smiles and warmth from the same people from the year before.   

As someone who loves to go to new destinations and try new properties, it is very hard to go anywhere else after experiencing Round Hill. It is a place we would love Pippa to get to know as she gets older.  

This place has become very special to our family.


The crescent shaped small beach at Round Hill is PERFECT!  The shallow waters off the beach are extremely calm and very lake-like, which make it ideal for kids and adults alike to swim. There is no shortage of Caribbean blues with bright turquoises every where you look!  There  are also two floating docks for sunbathing and just add to the family fun.  

Off the shoreline is a beautiful natural reef with an abundance of colorful sea life to explore either by the resorts glass bottom boat or with your snorkeling fins. There is no shortage of water sports right from the property. Stand up paddle boards, kayaks will have you covered.


It came as no surprise to learn Round Hill has been awarded one of the Top Luxury Family Destinations in the Caribbean. The Pineapple Kids Club and 7-Up Club welcome children ages 3-12. With several activities scheduled  for the children from: tennis, arts & crafts, basket weaving, movies and games, your little ones will not be disappointed. The Kids Club is managed by certified professionals and the care is included in your stay.  There are also ‘Mary Poppin’ like nannies available for a 3-hour minimum throughout the day and night at very good rates.  The care they provide for your little really made us feel good and safe. The resort provides cribs, high chairs and even a reduced priced children’s menu. 


Dining on any vacation is a very important thing for me when considering where we will go.  When I learned that Round Hill had its own on-site organic gardens I was psyched!  

There are three restaurants at Round Hill and all beyond exceptional. I would highly recommend taking advantage of one of their all-inclusive meals plans. 

Breakfast at Round Hill on the Seaside Terrace may have been my favorite. I looked forward to the Escoveich fish with their steamed calaloo almost every morning. I also enjoy knowing I could have some of their local micro greens, fresh from their gardens with their homemade lemon vinaigrette for breakfast. Every chance I had I indulged in the local Jamaican fare.  Pippa particularly enjoyed the fresh fruit and smoothie bar where we introduced her to a lot of tropical fruits!

The restaurant at Round Hill also features  James Beard chef, Martin Maginley whose philosophy of “ Lean Clean Caribbean Cuisine” is off the charts, specializing in locally crafted, custom Jamaican specialities. 

Every afternoon at 4pm Tea is served along traditional tea sandwiches and pastries. 

Round Hill at night is fabulous!  Evening attire is island chic. Who doesn’t love that?! We would dress and make our way for pre-dinner cocktails in the dimly lit, old-world, open-air bar. Black and white photographs of all the Hollywood A-Lister guests who visited, line the walls. On a typical night, there will be piano for cocktails followed by local live Jamaican bands beating to the sounds of steel drums and the hymning Reggae.    

Each night of the week, Round Hill offers a different themed dinner or events from cocktail parties with management to  beach BBQ’s, Farm to Table or Jamaican night.


Saving one of my favorite features of this place for last.  Not only is there a state of the art fitness center with a customized fitness schedule, there are also running trails on the property.  Follow the hill past the organic gardens where you are then reach the highest peak of the property.  There you will see Montego Bay in the distance and an entirely different view of the island than you will have from your villa or room. I prefer early in the morning to catch the most magnificent views of the sunrise from the East.  If yoga is your thing, try out the Open Air Yoga Studio at the fitness center.  Daily customized fitness classes or personalized tennis instruction also get your day at Round Hill off to a good start. 

The Spa and the grounds at Round Hill are special.  The walk alone from the resort to the Spa is worth doing.  Pamper yourself in one of the luxurious treatments or just snuggle on one of the hammocks swaying to the sweet island breezes.

In full disclosure, both times we visited we did not leave the property!  There was no need to nor did we want to.  While there are many great adventures waiting outside of the resort (the hotel concierge will assist you with all of these), I tend to like to stay put and do nothing when on this type of vacation. 

Some favorite things to do nearby are visiting the rainforest and waterfall tours. There is no shortage of prestigious golf courses nearby. Transportation will be provided to the nearby Tryall Golf Course, which is one of the Caribbean’s top courses. There is also the White Witch Golf Course, Cinnamon Hill and the Half Moon Golf Course nearby.  Daily shuttle service from the property is also available to visit Montego Bay. The concierge at Round Hill will be able to assist you with any activities off-site you wish.  

For those who love to shop on vacation, as I do, you must pay a visit to @Strawbossrichard right on the property.  Richard’s gorgeous handwoven baskets, hats, hampers and more have all made their way into our home.  There is also a gift shop and boutique onsite.

Round Hill will charm you!  The ease of getting there, being there and experiencing Round Hill will have you going back for more. You will miss the Round Hill family when you are not there and count the days until you can return.  Thank you for taking such great care of this little family of mine and providing some of our most treasured first family memories. Until next time beautiful place…

No Comments

Sorry, the comment form is closed at this time.