Round Hill Travel Diary

Grandparents were available and our schedules miraculously opened up, so we booked a last minute trip on a Thursday and were in Jamaica just a few days later. We do a February trip every year, just us two. It’s always a nice chance to decompress after the holidays and thaw out from the cold, but mostly to discuss the year ahead and plan out action items. Achieving multiple big, important conversations at home honestly feels impossible sometimes. I’m so thankful to my parents for giving us these 3 - 4 nights every winter because, outside of the work planning component of it all, it’s really just so good for our relationship and I look forward to it every year.

Round Hill Resort:

Round Hill has been on my radar for quite some time. It just oozes timeless, barefoot luxury. Designed and partly owned by Ralph Lauren (amongst a small list of other villa owners), it operates as a boutique hotel with 1950s Caribbean charm.

I should mention before typing this that we paid for our trip at full price and they don’t know who we are or that I’m writing this! I normally don’t do full on reviews of properties, so I wanted you to know up front that there is absolutely no bias at all. We actually booked our trip through Emily West, whom we book most all of our travel with these days. She is a high-end travel advisor and always knows the best new spots, the old classics worth visiting, and all of the insider tips & tricks of traveling to each specific place. Another plus is that you get lots of perks through booking with her, like daily breakfast, a resort credit, etc. Also, how cute is her website?

This beautiful resort (yes, it’s a resort even though it feels like an elegant boutique property) made such an impression on me, so of course I wanted to fill in all of my people. :)

Getting there:

We flew from Charleston to Charlotte (about 35 minutes) and Charlotte to Montego Bay (3 hours). From there, it’s a 25 minute taxi to the hotel.

We pre-arranged a private car (taxi) from the Montego Bay airport to Round Hill. Emily arranged this for us, but it’s also offered directly by the hotel and is added to your final bill. It’s $50 each way (this covers up to 4 people). I highly recommend this! We’ve done a good bit of island hopping and I always find the taxi situation to be such a pain because you never really know if you’re getting swindled (happens more than you’d think), so having a prearranged taxi that is affiliated with the property brought peace of mind.

Another thing to note is that the hotel offers a third party service called Club Mobay, which is like a VIP fast track service through customs and security at the airport. They greet you off the plane with a sign with your name on it, then guide you through the various checkpoints. It’s $50 per person each way. We denied this service because we didn’t think it would be necessary and can now confirm that we are happy with that decision. The Club Mobay lines were honestly about the same as the regular lines. While the Montego Bay airport is way bigger than any other Caribbean airport I’ve been to, it was very easy to navigate and not overcrowded at all. However, peak travel times, like during spring break, might be a different story and it might could be worth it then!?

Accommodations:

There are hotel rooms, suites, and villas on the property. We booked a one-bedroom suite that was atop the hill and had a plunge pool. It was fantastic!

Just to note, there are no TVs in the rooms, but I promise you don’t miss it.

Activities + Experiences on Property:

They’ve got a pool and a private beach area with tons of water toys, like kayaking, paddle boarding, snorkel gear, and more. There’s also plenty of tennis and pickle ball courts, basketball, and a really beautiful gym. A Kids Club is also on property!

Every day at 4pm, they set up a beachside tea under the terrace. Complete with little english cookies and clotted cream, homemade doughnuts, tea sandwiches, crudite, freshly popped popcorn, and various drink options like tea, coffee, etc. This was quite the hit! Some come still dressed in their bathing suits, some freshly showered for an early dinner. We would take our mini mahjong set everyday and play while enjoying sweet treats and coffee before going back to our room to freshen up for dinner.

There is also a beautiful spa on property. There aren’t amenities (as of now, at least) that include things like a sauna or steam room, but the massage I had was the best I’ve ever had and the setting couldn’t be more beautiful, as many of the rooms are on an upstairs terrace that overlooks the bay.

We walked the jogging trail, which goes around the property, every morning before breakfast and it was such a highlight!

Dining:

We really looked forward to meal time because the overall experience of it all was so nice. The food was consistently tasty. The Round Hill team grows their own micro greens on property, so it was something I noticed in most recipes, even just as a garnish.

There are lots of places to eat on this very small property! Within a fairly small area, there’s an upstairs open-air dining room, a seaside terrace and bar area, a beach bar, and a pool bar — each with a different food menu. The various menus almost overwhelmed! (We had just gotten the hang of what was on each menu when it was time to go… ha!)

When it comes to dinner in the upstairs dining room, which is the fine dining option on property, the menu changes nightly to go along with whatever the theme for the evening is. You can preview the menu schedule for the week on their website and also see the menu for each evening displayed in the lobby every day.

Breakfast was such a highlight for me, but I am just a big vacation breakfast person. It’s the only time I ever sit down for breakfast. I love orange juice but it’s the only time I ever drink it. I love the stillness in the air and impending excitement about the day. I just love every little thing about breakfast on vacation—and Round Hill’s breakfast totally set a new standard for me. It’s a white table cloth service, which felt very special in juxtaposition to the salty, open-air view. The coffee is served in a Ralph Lauren tea pot, with matching cups and saucers. The menu was large and delicious! In addition to both of our breakfast meals, we ordered something to share on two of the mornings—the french toast and the smoothie bowl. GET THE SMOOTHIE BOWL. Wow, just wow.

Service:

The team at Round Hill was the friendliest group of people I’ve come across while on vacation. They were so lovely and welcoming. (I can’t always say the same when it comes to other islands.) When we left, I genuinely missed seeing their smiling faces and hearing their warm hellos. It made the whole experience!

A few final tips and thoughts:

We stayed 4 nights and it was honestly perfect. I would maybe go for 5 nights but I don’t think I would book for longer than that because it is a small resort, after all, and there’s only so much to do. We enjoy breaking up longer trips by trying different off-site lunch spots, for example, or shopping around the area. While there wasn’t any of this happening in or around Round Hill, we didn’t miss it at all since we were just there for 4 nights. (However, we maybe would have yearned for some daily action like that had we stayed for longer.)

If you’re traveling with just your significant other and don’t have an overly lengthy flight to get there, I would even go for just 3 nights! Since you’re staying in place at the resort and there’s no reason to leave, I really think you could leave feeling like you had a very full long weekend.

In summary, this beautiful resort really made an impression on us. It has such a point of view and we really loved our time there. For the first time ever, we were already planning a return trip before we even left. We want to bring our children because I know they’d enjoy it as well.

It’s a truly special place and I highly recommend it, but I’m sure I forgot something. Let me know if you have any questions in the comments! x