Round Hill resort is a boutique hotel in Jamaica that opened in the 1950’s and has hosted celebrities like John & Jackie Kennedy, Grace Kelly, Harry and Megan Markel and Pierce Brosnan and is a place that fashion designer Ralph Lauren likes to call home. Round Hill was an old Pineapple plantation and built in 1953 by John Pringle, a Jamaican native. John studied over seas and he met and knew a lot of famous people over seas and he wanted to build a resort where they would all come to visit and own villas. He was able to get investors to help build the resort as well as villas on the 100 acre Jamaican peninsula. Ralph Lauren owns two villas here and has designed the 36 room, Pineapple House.
The resort is timeless and elegant with so much charm. The moment you drive down John Pringle drive and arrive at this gorgeous lobby seen below, you are in awe. The staff is so kind and greet you with a huge smile, professional uniforms, and a “welcome home.” They all work to learn your name and it has all the feels of a wonderful country club without any of the stuffiness.
This resort is one that has been on my list of places to visit for while and I knew I would love, but I wasn’t sure how much I was going to love the island of Jamaica. After being here, I see what a unique and special place it is with so much history and beauty. I am so glad we came to check it out.
Before arriving, I read a ton about the resort from my friend Mary Weiss who has been coming here for many, many years. It was so nice fun to read her experiences and reviews. She has come on girls trips, couples trip, with just her family and then with all of her extended family. It is truly that kind of place. It would be a really fun place to come with extended family to rent one of the larger villas on property. For this trip, Matt and I came just the two of us and it was nice a place to relax and retreat and we did just that. I had Melanie, our travel agent, book it for us and they were running some pretty good deals since it was “off season.” I will share more about our beautiful villa below.
HOW TO GET TO JAMAICA
The best part about Jamaica is that it is pretty easy to get to. It is a short flight from Miami (about 1hr 20 min or so) and about 2.5 hour flight from Charlotte. We flew into the Montego Bay airport which is a really nice size airport for a Caribbean Island. One thing that I learned about at this airport is a service called Club Mobay. It is an extra service that you can purchase online to help speed your way through all the customs lines and be personally escorted through the airport at your arrival. Honestly, we had no idea about it and somehow got really lucky by asking the right woman a quick question and I swear she just gave us the service with hopes that we would give her a nice tip. Which is exactly what happened and we were thrilled. On the way home, Club Mobay was already full (so book it early if you are interested); but the concierge at our hotel set us up with an airport escort and again, we just gave him a nice tip and they whisked us through all the lines. The advantage of Club Mobay is that you get to access their VIP lounges and get complimentary drinks and I think that’s it. From the airport, Round Hill is only about a 20 minute drive. You can contact the concierge to set up a car service.
WHERE WE STAYED AT ROUND HILL
We stayed at the Round Hill resort in a one bedroom suite. Round Hill is known for its 27 gorgeous villas ranging from one bedroom to 6+ as well as the Pineapple house which has 36 oceanfront rooms that our beautifully decorated by Ralph Lauren and set overlooking the hotels Infiniti pool.
We chose the one bedroom suite because we were really set on trying to find something that had our own dip pool and since we were headed here in “off season” we were able to snag a really great rate on this one bedroom suite. It gave us the privacy we wanted plus an absolutely amazing set up. This one bedroom villa was WAY more space than we every needed with 3 floors which included two nice living spaces, 3 bathrooms (one on each floor), a kitchen, bar, and master bedroom and bathroom. You felt like you could easily sleep 4-6 people in here but that was actually only one bed in the whole place. I heard someone say that they could arrange to add another bed in one of the rooms if requested.
One issue we did find in our one bedroom villa during the time of year we were there is that it was super hot when we first arrived (they definitely needed to go in there before our arrival and turn down the AC) and that the master bedroom was designed with no windows, only screens. So the master bathroom was basically open to the elements and being that it was end of July, the elements were HAWT! So in our house, the master bathroom and the stairwell going to all 3 floors which also just had screens for windows; were always quite steamy in July. Thankfully the AC worked well in our master bedroom, but we had to always make sure that our bathroom door was closed and the door going to the stairwell was closed so all of the hot air was not getting in. I am not sure the set up for all the other rooms/villas on the resort, but I imagine they are somewhat similar. The design of a lot of these villas is to be an “open air” concept where the doors slide open in the home to open up to the beautiful outdoor spaces, pools and views. With that being said, that is also the concept with every communal space throughout the resort including the lobby, dining room, bar area and library. So you can see how in cooler months, this is both gorgeous and appealing; but in the hottest part of the year, it can be a little steamy 🙂
We were located up the hill a little bit from the main lobby and beach area, so we would call down to the bellman to request for a golf cart pick up whenever we needed. I have been to places that sometimes this can take quite a bit of time, but not here! They were so quick and I swear we never waited longer than 4 minutes. That was a nice treat.
Another thing I will mention about our villa was that there were no TVs. Honestly, we were probably a little shocked by that more than anything; but we truly never missed them. I liked that it forced you to sit outside on the porch under the stars, take an evening swim or enjoy a book rather than be on the TV. I mean, we are only talking a few days…so we managed to live without it 🙂
Other Jamaican hotels considered:
Tryall Club – This resort is just down the road from Round Hill and maybe a 1o minute drive or less. We had lunch here one day and enjoyed getting a quick look at the resort. It looked really nice with a great pool and beach area. We sat at the outdoor restaurant for lunch and had a great meal. They also have a golf course right on property for those that are there to play golf.
Half Moon – This is a larger resort that was probably 30-40 minutes away from Round Hill that is supposed to be nice and have a little more action than Round Hill if you are looking for that. We had dinner at one of their restaurants here, but unfortunately we didn’t really get to see much of the resort because the restaurant was across the road at their golf course area and we got there at dark.
The Rock House – This resort is a more budget friendly option with no beach but a rocky coastline to jump in and enjoy the beautiful water. Each villa had a fun and unique feel and could be a really fun option. If you did want to hit the beach, you can get on a free shuttle to their sister property, the Skylark hotel as well.
our villa #214
Below is our master bathroom that got a little steamy with the screened windows.
THE BEST PLACES TO EAT IN JAMAICA
The food at Round Hill was delicious. If I could go back and enjoy breakfast every morning at my same exact table overlooking the water with my fresh eggs and fruit, and pineapple china sipping the most delicious coffee, I would!! Now I understand that if you rent one of the villas on property (2 bedrooms or larger), you have a chef that comes and cooks and serves breakfast for you every morning at your house! How great is that???
Round Hill has one main dining area that serves dinner most nights, but they also change up the locations throughout the week. They have themed meals that change throughout the week and the location of dinner might change up as well. They have a Jamaican night buffet one night which was incredible on the terrace and I hear the Monday night beach barbecues are not to be missed, but sadly we were not there over a Monday night. They pride themselves in farm to table as they grow many items right on property. I tried ox tail and curried goat for my first time here which are two popular Jamaican dishes and were quite tasty.
Something to note in Jamaica is that the food is good and it is all very authentic. The Jamaicans are very proud of their food and not scared to shy away from their local spices and flavors. So just know that you will be eating a lot of things like jerk chicken, rice and peas, curried seafood, and even goat… all things that are native to their culture.
Other options off property:
Tryall Club – We had lunch here one day and I highly recommend heading here to check out the resort one day. It was fun to see and my shrimp and avocado wrap was delicious.
Sugarmill – This is a nice restaurant over at the Half Moon resort property. For us, it took way too long to get there with traffic and did not feel worth the drive. I would save this spot for dinner only if you were staying somewhere closer to Half Moon.
House Boat Grill – We never made it here, but this is a spot you can hit if you are wanting to get off property that is a little closer ride from the Round Hill resort.
Marguerites – This is another spot that we had a reservation at for one night, but we ended up deciding to just stay at our hotel and eat there rather than hop in a car and try to go off property.
THE BEST THINGS TO DO AT ROUND HILL
The stunning 30 acre resort located in its perfect, private cove has a lot to uncover and explore right there on property. From the beach, to the pool, to the spa and fitness center; you can find yourself enjoying time relaxing as much as you want or playing all day long. They offer fitness classes throughout the week, have boats you can rent right at the dock on property, and you can even grab snorkel equipment and hit the reef just off the Round Hill beach.
If tennis and pickle is your thing, they have staff on hand that teach tennis clinics, private lessons or will even just hit with you if you want to get out there for a bit. You can rent the courts by the hour (hard and soft courts) and play a match with friends and family too.
They also have two small buildings on property that are so cute. One is a small library that looked so inviting, but I never went in to really sit and enjoy; but the other was a really cute room that had a couch, TV and card table. It looked like the perfect little spot to get a Mahjong game going 🙂
Below I am sharing a little bit of things we did on and off property. I will say that we felt like Jamaica was one of those islands that we were probably happiest just being at our beautiful resort and staying and enjoying it. We ventured off and tried a few excursions off property and they were not our favorite. You can read more below, but I think it is important to mention.
Explore the Property – Matt and I did this on our first full day and loved walking around everywhere and seeing the sprawling beauty of the entire resort.
Rent Boat at Round Hill – They have a hut right on property with a dock that you can rent boats, hot dog tubes for the kids or hire a captain for the day.
Spa at Round Hill – I highly recommend taking some time to enjoy the spa. I had a 1.5 hr massage with Althea and she was incredible. She massaged my scalp and face down to my toes and was amazing.
Tennis and Pickleball – Grab some family to play with or schedule some time with a pro to hit or take a lesson. I hit with the pro, Ian, and he was awesome.
Afternoon Tea – Every afternoon from 4-5pm they serve tea and light bites in the bar area that you can enjoy. Bring your cards or just sit and enjoy a cocktail.
Kids Club – The kids may love checking out the kids club for a day and enjoy activities throughout the property. They even have soccer field on property which was really cool.
Things You Can Try Off Property:
There were quite a few things that I saw for excursions in Jamaica off the property, but the main thing to keep in mind is that the island is large and many things I was looking at were very far away. So do your research before you book things. These are a few things that were relatively close to the Round Hill property.
Catamaran Cruise – We signed up for a group catamaran trip for a half day experience just so that we could get out on the water one day and do a little snorkeling. It was a large catamaran with probably 50 or so people on it and they played music and served drinks on the boat and provided the snorkel gear. We went to one snorkel spot and saw a reef with some fish, but nothing crazy. I wouldn’t highly recommend this; but if you were traveling with a larger group and could swing a private charter, that would probably be a fun option.
Mayfield Falls – This is the waterfall adventure we went on that I can say you definitely should not do. It took almost two hours in the taxi to get here and it was a terrible drive all the way there!!! The roads were horrible, full of pot holes, and it was a scary two lane road all the way there. I had no idea it was going to take so long and it was definitely not worth it! I hate saying this because this is locals lively hood up there at these Falls, but it did not feel like a safe drive at all. I was picturing this being a super popular, must-see spot and we were the only people there. Our guide was super nice and once we were there, we honestly had a a fun time; but I just don’t think we had any idea what we were getting ourselves into!
Mountain Valley Rafting – This seems like a popular thing to do in Jamaica to go on one of these bamboo rafts down the river. We did not do this on our trip, but wish we had done this rather than the Falls mentioned above. This was a much shorter drive that we actually passed on our way to the Falls. I would say it was maybe a 25min drive or so from the hotel. Again, we didn’t do this, so I am not exactly sure how exciting this is; but if you are looking for a little adventure, this could be worth it.
Golf at Tryall Club – This is a beautiful resort and the closest golf course to Round hill if you are looking to play a round of golf on your trip.
Rose Hall Great House – This is not something we did on our trip, but I have heard that guests like to tour Rose Hall Great House, a restored 18th-century architectural masterpiece. It is home of the notorious White Witch of Rose Hall: Annee Palmer. Known famously to have killed three husbands and taken on numerous slave lovers, only to die by the hands of the one she loved the most. They offer day and night tours where you will be guided through the home and its beautiful botanical gardens.
THE BEST TIME TO VISIT ROUND HILL
I think this is definitely a spot you can enjoy year around, but it is probably at its best during the winter months. I hear the time here during Christmas and New Years is absolutely amazing and I can only imagine how nice the weather is during our Fall and Spring months.
When we were there during July (height of Summer), it was definitely warm. They even said it was a bit uncharacteristically warm this year while we were there. I think they typically get at least some cooler weather in the evenings even in the Summer. As I mentioned above, they have a lot of “open air” construction in their homes and common areas; so you are living/eating in the outdoor temps a lot of times.
WHAT TO PACK FOR JAMAICA
Pack for this trip like any tropical vacation that you may pack for. I rounded up all my outfits for this trip right here in a blog post for you. I will also mention though, that if you are traveling with men, make sure to tell them to bring some slacks. They do require the men to wear slacks in the dining room after 7:30pm on property.
Final Thoughts on Our Stay at Round Hill
- This is a first class resort that is a wonderful escape for a long weekend. I would say 4 to 5 days here is the perfect amount of time. We stayed 4 nights and I that felt pretty perfect.
- Don’t forget to book Club Mobay when you book your flights to Montego Bay. If you can’t get Club Mobay, call the concierge at the hotel and ask if they can help you out.
- Enjoy your meals on property and maybe do one lunch and one dinner off property if you want to change it up a little bit.
- Take advantage of the activities that they have on the resort. The other excursions on the island were just tourist traps in my opinion 🙂
- Take a ride over to Tryall club to check it out. Enjoy lunch or schedule golf.
- If you can, make the splurge for one of the villas if at all possible. They are really beautiful and having your own pool is a really nice amenity.
- Don’t forget to tell the gentleman to pack pants for dinner. Men must wear pants to dinner after 7:30pm.
- The resort is kid-friendly and has a kids club, babysitter for hire in the evening, kids menus at the restaurants and activities for the kids to enjoy.
- Phew, if you made it to the end, I hope this was helpful! I try to include it all for you because I know when I am trying to plan a trip; I really appreciate a thorough review from someone. I would love to hear about it if you decide to book a trip here. It sure is a beautiful and special place.
I will just mention that this post is not sponsored in any way. We picked and chose this destination as a place we have wanted to check out and visit. I always like giving a full review on places we travel.
