Curator’s statement
Round Hill: a 1950s haven for the famous, royalty, the Illuminati, and anyone looking to disappear for a while in pineapple groves. It was originally a Lord’s Estate. Grace Kelly was a loyal guest. JFK and Jackie O preferred to stay in villa 10. Where Hammerstein wrote The Sound of Music. There’s even a noir snapshot of Princess Di waterskiing at the hotel. Ralph Lauren designed the rooms. It’s where Stella got her groove back!
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Trip overview
A dear friend, stylish client (she’s a real-life fashion designer, folks!), and newlywed just got back from her honeymoon. Instead of a hotel review, I asked her to do a honeymoon trip retrospective with me. Below is the output of the bride’s brainstorm—her must-haves, can’t-miss moments, and little luxuries.
Liked…
The vibe: Old-school luxury. You can feel its charm from the start. Loved the mid-century history—it felt like a true Caribbean icon.
Dancing to live music: Piano bar, a saxophone, and the perfect nightcap.
The beach was beautiful, the pool was peaceful, the Pineapple library is a good place to be.
Indulgent baths: Elemis products. Soaking tub and epsom salts. Robes, slippers, reusable water bottles.
Loved…
The service: Warm and relaxed. They somehow made everything feel special, but easy. Loved that they offered turn-down service. The complimentary afternoon tea on the deck was such a thoughtful touch, too. ”Every inch of this place was stunning and every staff member went above and beyond.”
All of the complimentary amenities: Snorkeling. Glass-bottom boat. Pickleball. Buy-up water skiing. “There are no TVs in the rooms, but we loved it. You won’t get bored here.”
Fora breakfast & spa credit perks: The breakfast spread is free (with perks!) & oh so good. Smoothies and omelets were repeat orders. “The spa was dreamy! We walked down a trail along the water, which looked like we were in the jungle… Did a couples massage and I also added on a Jamaican Coffee Bean Scrub which was awesome. Recommend doing any scrubs at the beginning of vacation before you get a lot of sun!”
Best drinks: Affogato and the coconuts at the beach hut.
Splurge that was worth it...
Private dinner on the beach. A trip highlight. Four-course meal.
First: seafood casserole (unreal).
Second: lemon sorbet (a palate cleanser à la Princess Diaries).
Third: blackened salmon and peppercorn-crusted ribeye.
Fourth: rum raisin bread pudding and chocolate banana cake (10/10!!!).
The cherry on top: the organic garden on-site.
Learned…
Get the airport perks: Easy 25 minutes away from the airport. Club Mobay VIP service.
Dress code: “Its the perfect mix of casual and luxury. You can be casual during the day and dress up as much as you want for dinner.” That being said, after 7:30 pm men must wear pants (except for BBQ Mondays).
Family-friendly: Pineapple Kids Club. Cribs and highchairs are available at no extra charge. Early dining options with children's menus.
Packing list: You can’t have too many swimsuits. Beach bag. Sun protection. Chic cover-ups for afternoon tea and the beach bar. Light dresses for dinner—it’s hot. Bold prints. Lively colors.
Need to know
Longing for…
More time at Round Hill. Could’ve stayed at one hotel the whole week. Instead of trying to pack in more variety, lean into fewer hotel and location changes and embrace island time.
A touch of adventure: Still on the bucket list—Dunn’s Falls, the luminous lagoon, and zip-lining.
Rewind moment: Beach read in one hand, affogato in the other.
For more inspiration and insider recommendations, visit our Jamaica page.
Travel Advisor
Sydney Getzin
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