Our Jamaica Trip

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.

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It’s all stripes, black and white checks, blue and white ceramics and beautiful wood.

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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.

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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.

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The view from our room!

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Again, such beautiful plants and flowers! Such a welcome sight in the middle of a cold winter!

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Love the Colonial Carribean design of the buildings and the complete indoor/outdoor style of every space.

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The view from a villa up the hill.

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The beach is small, but so relaxing. There are gorgeous trees that offer shade when you want it too.

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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! :)

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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.

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View from the pool down to the beach (past one of the beach bars, of course).

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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) :)

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Another gorgeous spot to lie, read and nap.

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Every corner of this place is interesting and pretty! Even this little stairway up to one of the restaurants.

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There is the most stunning path along the water to the spa and gym.

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You walk past this little beach covered in bleached white coral rocks that make the most amazing sound when the tide washes over them.

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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.

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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.

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Looking at this just makes my blood pressure go down.

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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.

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The stairs up to the rooms with this adorable stripe detail I plan to file away for future beach house projects! Love it!

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Our room- a big open window (some rooms have balconies too) and was perfectly lovely.

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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!

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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!

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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!

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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.

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Up above the patio is the more “formal” dining room where dinners were served some nights and breakfast in the morning.

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And one night there was a beach barbeque that was incredible!

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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.

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And they have this amazing organic garden that they grown many of their own vegetables in (and I ate many of them- yum!)

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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.

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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!





  1. So glad to hear you had some legitimate down time. You deserved it!

    My best friend’s daughter had her wedding held at Round Hill a few years ago. It was perfection. They reserved a few of the guest cottages for the family, while the rest of the guests stayed in the main hotel. It was fabulous.

    Welcome back to the ice and cold!

  2. Sold! Looks perfect. I’m putting it on my to go list.

    I live in Bermuda which is a direct 2 hour fligth from Boston. If you have never been, I think you would definitely enjoy it (but not in the winter, it’s not beach weather here at the moment.) Lots of adorable pink houses and amazing beaches!

  3. Thank you for bringing the sun and warmer temps back to Boston with you!!

    If you’re ever looking for another place to escape to for some laid-back luxury , I HIGHLY suggest Cap Juluca in Anguilla: http://www.capjuluca.com/

    Not quite as easy to get to (unless you have a private plane) but totally worth it (and celebrity sightings abound)…

    Welcome back!

  4. Erin, I have been reading for a while and love your style ( as do so many others! ;) The trip was amazing, and having lived on an island for a couple of years, I grew to love the textures around me. You feel so connected to nature, and the atmosphere around you is so enveloping! I hope you do go back often. Also, regarding some past posts, including Andrew’s, is to not be too hard on yourselves. Sometimes our limitations ( and having had cancer I now have many) turn out to be our greatest blessings. God Bless!

  5. Beautiful photos and thank you for sharing! Dreaming of sun right now from NYC! Glad you both had a wonderful time.

  6. Erin – this looks amazing! My husband and I do a “no kids” vacation every fall, and this definitely made the list. What airline did you take that went from Boston non-stop? I thought you had to go through Miami (or similar). Any place I can get to non-stop is so much more appealing!

  7. What a stunning resort! There is just something so special about the Caribbean and that resort looks like it captures all the charm and beauty of the islands. Jamaica is one of the islands I have never visited but after seeing your gorgeous photos, I am putting Round Hill on my list! I love the style with the dark woods, whites , lush greenery and stripes. Thanks for sharing your wonderful vacation!

  8. I enjoyed all your photos and stories about Round Hill until you got to the tea and scones. Now my stomach is growling and I must go feed the beast. Thanks for sharing this wonderful trip with us. We’re happy you both had such a wonderful time.
    Honestly, I thought you picked this place because of the decor; it’s so Erin! But I see it has a lot of other stuff going on too….

  9. I got chills reading your blog. We have traveled to Round Hill three times as a family and stayed in a villa. It is the most special place. You described it perfectly. It is simply elegant but rich in texture. The very best part though, is the warmth of the people. A trip to Round Hill heals the soul.

  10. Oh Erin, how lovely! I’m glad you had such an amazing time. Well deserved :)

    You also may have just shown me the perfect place for my honeymoon! How close were you to town in the event you ever wanted to leave this magical property?


    1. Not close- and there isn’t much of an “in town” anyways. There are various day trip they offer to swim with dolphins, tour Rose Hall and see some great waterfalls though! We never left, and felt no need to!

  11. We have been to Jamaica several times but have not been to Round Hill Resort. I hesitate to visit this lovely resort because I have been cautioned that the resort is in a flight path and you hear jets overhead every 30 minutes or so. Was this your experience?

  12. Erin, That was such a special place! Thanks for sharing! I wish we could go there sometime!
    Is it all inclusive?


  13. Every time I see the b/w stripes…I love more and more…and with that royal blue…Round Top sounds wonderful!! franki

  14. Ah. Roundhill would be a dream!! My husband and parents went to Jamaica last year, and we looked into RH, but had to settle on Couples San Souci–but, I highly recommend it, as the grounds are so similar and the service/food were impeccable! The rooms, not so much, but thankfully we were rarely in them! Jamaica is definitely a special place!!

  15. WOW! Breath taking, Erin! Haven’t been to Jamaica since November 2013 and I feel like booking a trip right about now. Canadian winters are so harsh; I wanna get away from the -30 Celcius we are feeling today!

  16. I have heard great things about that beautiful place and this (wonderful, detailed) post confirmed them all. It seems that after all you’ve been through last year, this trip was very well deserved! I was recently in Seychelles with my husband and some of your photos were reminiscent of our time there. Seychelles is neither a direct nor short flight for you, but if you ever have the time to go, GO! So magical and romantic, a truly unforgettable experience. Thanks for another great post!

  17. Thank you for another place to add to our “Must Do” list! Your virtual tour was wonderful, and I feel like you really gave us perspective from all angles–as of course you would!!! Our family(seven of us, including three college aged children and two significant others…we had three of the 27 rooms!) has just returned from our fifth trip to Hermitage Bay in Antigua…it is perfection, and Round Hill definitely looks on par–I checked it out for next year, and unfortunately, they require a two week minimum stay during the holidays–oh well, looks like this will just have to be a trip for my husband and me : ) Definitely hope you’ll look at Hermitage Bay–check out the Tripadvisor (mine are under” Shockly”–our bichon)reviews and I think it will go on your bucket list, too!

  18. Hi Erin – loved this post on Round Hill. I went over 10 years ago with family, and that trip is still one of my most favorite memories. You summed up the resort perfectly – the only thing I’ll add is that the staff there make you feel like you’re the most important person in the world. They catered to our every need and were just fun to be around every day. It was fantastic and I definitely hope to go back one day!

  19. Wow! What an amazing resort. Jamaica is somewhere I’ve always dreamed of visiting. I just checked how long it would take us to get from Doha to Jamaica…36 hours!

  20. Hi,

    I am glad you enjoyed your stay in JA. My family is from JA, and its so nice to here when people go down and have an amazing time. Another really nice part to visit is Negril. They have some really up and coming boutique hotels. It is still has a natural element like Round Hill Hotel, and as a designer I think you will love the natural beauty and warm colors.

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