After the book tour and the stress of our first (failed) round of IVF, I figured Andrew and I were due for some serious relaxation. We knew we wanted to go somewhere we could get to on a direct flight that wasn’t insanely expensive that also took our saved points and miles from rewards programs we had. We basically spun a globe and pointed and ended up with Jamaica. An easy direct 4 hour flight from Boston, we figured it would be perfectly sunny and after some research, settled on Round Hill Resort in Montego Bay. I’d heard of it before, but never seriously looked into it (other than Ralph Lauren’s villa there!) Turns out, my grandparents went a few times back in the 50’s/ 60’s too! So we just booked it (and yes, we paid for absolutely everything, no sponsored anything here) and didn’t think twice. And I’m happy to say, it was PERFECT!
Round Hill is the most charming, old school meets modern day resort. Truly.
Such classic design (updated by Ralph Lauren, whose house, as a mentioned, is on the property). Simple but totally lovely- just enough luxury but no stuffiness AT ALL.
It’s all stripes, black and white checks, blue and white ceramics and beautiful wood.
The landscaping and greenery on the property is to die for. It’s so lush and tropical, unlike any other Carribean resort I’ve been to.
There are hotel rooms that are all ocean front with a gorgeous view, and a bunch of villas as you go up the hill from the beach. The villas are perfect for those traveling with family or children, lots of room to spread out, your own private pools and unique design in each villa. If your going with just your significant other or a friend/family member I’d suggest staying in the hotel, The Pineapple House. It’s so lovely and convenient.
The view from our room!
Again, such beautiful plants and flowers! Such a welcome sight in the middle of a cold winter!
Love the Colonial Carribean design of the buildings and the complete indoor/outdoor style of every space.
The view from a villa up the hill.
The beach is small, but so relaxing. There are gorgeous trees that offer shade when you want it too.
Then there is the new infinity pool next to the beach- we would switch from ocean to pool through the day, which was so nice! Note the rainbow! :)
It’s lovely to be able to look at the ocean from the pool. I swear, this was the most relaxing vacation I’ve ever been on. I was able to completely unwind and enjoy doing absolutely NOTHING.
View from the pool down to the beach (past one of the beach bars, of course).
I liked sitting here next to the rocks where you could catch a nice breeze and lots of sun (that’s Ralph’s house where the white wall is) :)
Another gorgeous spot to lie, read and nap.
Every corner of this place is interesting and pretty! Even this little stairway up to one of the restaurants.
There is the most stunning path along the water to the spa and gym.
You walk past this little beach covered in bleached white coral rocks that make the most amazing sound when the tide washes over them.
The spa (where I had the most amazing massage ever, seriously) and the expansive green lawn where we hung out all the time after we were done with the beach and pool.
I mean, come on. It was insane! This spot has the BEST breeze and is so quiet we felt like we were on our own island.
Looking at this just makes my blood pressure go down.
We sat here many times with a glass of wine and just thought “how lucky are we?” Truly, I felt to blessed to be able to enjoy this place.
The stairs up to the rooms with this adorable stripe detail I plan to file away for future beach house projects! Love it!
Our room- a big open window (some rooms have balconies too) and was perfectly lovely.
Some other photos from the website since I forgot to take other pics of the room before we messed it up! But it loked exactly like this- the bathrooms were all renovated with Waterworks fixtures and was complete with a huge soaker tub!
The chic bar where we’d settle in for a cocktail after a long day in the sun (they also have kayaks and paddle boards you can use for free). I love the design, of course!
Striped banquettes and tons of black and white photographs of guests from time past (we spotted Paul McCartney and Pierce Brosnan). It was such fun looking at them all!
And the food. OH, THE FOOD! Such amazing meals at every turn! We didn’t have a single bad meal the whole time. This is the main patio where you eat lunch and some dinners.
The patio at night was so delightful with string lights and music.
Up above the patio is the more “formal” dining room where dinners were served some nights and breakfast in the morning.
And one night there was a beach barbeque that was incredible!
And every afternoon there is a proper tea with the best snacks EVER. I’m not kidding, I ate my weight in warm scones and run balls. And the fruit! I never new mango and cantaloupe could taste like that. I know, I sound like I’m making this up, but I literally am head over heels for this place.
And they have this amazing organic garden that they grown many of their own vegetables in (and I ate many of them- yum!)
While there were no TV’s in our room (which actually was nice) there is a main living room where Andrew could check the football game scores. :) And it’s cute too, bonus.
A big painting map of the property. What’s really interesting was that almost everyone we met or overheard talking was a return visitor- many people who come every year, one woman who comes once a month in the winter, and many people who were on their fourth or fifth visit. And I can see why! It’s such a welcoming, warm place where you don’t feel hassled at all, but your every need is met.
I was legitimately sad to leave. It was just awesome. :)
And thankfully, we popped into a cocktail reception for an an art show one night and was so pleasantly surprised by the watercolors of local artist Patrick Waldemar. I picked up this gorgeous little abstract landscape to commemorate the trip.
So obviously, I highly recommend this place and Andrew and I are already planning a return trip!