Why book?
To feel like your family has passed a vacation home in Jamaica down through the generations, with each round leaving it better than than the last.
Set the scene
It takes 20 minutes or so to transfer west from Montego Bay’s airport to Round Hill’s front gates, and there’s a good bit of city and country to soak up on that drive. When my van pulls in, segments of the staff are wrapped up in a game of footy on a lower field just past the entrance—guests have gathered to watch, and we’re promised that there are more matches to come should we want to spectate ourselves. Everyone here is interested in each other (genuinely, never nosily) and casual chats with friendly staff and fellow guests alike come easily, and even the most misanthropic among us will find themselves opening up in the warmth of the atmosphere. Mix in an undeniable chic—Ralph Lauren-designed digs, James Bond pedigree—and you’ve got to be feeling at least a bit sexy.
The backstory
Jamaican-born entrepreneur John Pringle opened Round Hill in 1953, using his insider status to build up what would become a veritable playground for the rich and famous on what was, at the time, an undeveloped stretch of paradise. And while the resort and its surroundings remain pastoral, low-to-the-ground, demure, there’s a sprawl nevertheless—it’s an Edenic compound, one where any people who may be just around the corner feel worlds away. Proof of the sophisticated, cosmopolitan party scene that thrived here while Pringle reigned can be found in the Grill, where framed black-and-white photos of notable guests—from Paul McCartney with an infant Stella to Michael Douglas—hang on the walls. John F. Kennedy even holed up here to write his inaugural speech.
The rooms
If you’re staying in one of the Pineapple House’s 36 rooms and the clean white interiors offset by crisp navy and pink accents bring to mind the stylings of Ralph Lauren Home, you’re not at all off base. Lauren, who owns a villa on the property, designed them himself. His philosophy posits that nature should be the focus of any space, and this is true—trappings frame and do not distract from the views. There are four types of rooms: Ocean View and Premium Ocean View options sit on the upper level and boast cathedral ceilings and large windows, with the Premium selection enjoying furthest proximity from the nearby pool and beach for utmost seclusion. On the lower level lie the Oceanfront Balcony and Premium Oceanfront Balcony rooms, with the same factors distinguishing Premium from not. What these options lack in vast airiness, they make up for in their titular balconies.
If you spring for the villas, expect a tad more variation. Each of the 26 rentable options are individually owned, and range from two to six bedrooms. Across the board, they’re homier and more spacious than the rooms found in the Pineapple House—shared living spaces, pools, kitchens, outdoor showers, the amenities list goes on and on. But the devil is in the details. Bookshelves are crammed with novels and almanacs, the wood boards of the ceilings stained dark in delicious contrast to the clean white walls and creamy linen furnishings.
Food and drink
Flagship restaurant at Round Hill (also designed by Ralph Lauren) serves up fresh Caribbean food that burns clean with ingredients from the onsite organic gardens. Highlights include jerk mac n’ cheese, oxtail ravioli, and scotch bonnet ice cream. The Seaside Terrace and private in-villa dining (including breakfast) are also fabulous, more casual options, but my personal favorite meal comes at Afternoon Tea. Laidback and self-serve, this 4 p.m. heaven is all about the tea sandwich. Housemade biscuits and tea on tap are also particularly good.
The spa
It’s a bit of a hike from the resort’s main campus to the spa—the path winds along the beach for nearly two kilometers before you reach the facility, a grand 18th-century plantation house flanked by a double stair—out front is a soaking pool that’s decidedly adults-only. Treatments are simple and effective—massages, facials, scrubs. The gym is also here, with fitness and yoga classes from, among others, Donovan, whose charisma is so profound that he played himself in How Stella Got Her Groove Back when that film was made here 25 years ago.
The neighborhood/area
Make no mistake: this is a bona fide resort, and as such the insular will find little need whatsoever to leave the premises. But it’s a twenty minute drive into Montego Bay proper, where most guests tend to venture to experience Jamaica’s nightlife. Legend has it Michael Jackson asked his security to keep fans away from him at a local dive bar, only to become upset when the locals were all too good at treating him like a normal person. Day trip options include excursions to rum distillery Appleton Estate and a visit to YS Falls for ziplining and swimming.
The service
Most of the staff at Round Hill has been working there for over three decades—some fresh faces are mixed in, of course—and the service is delightfully friendly. Even the hardest-hearted antisocial skeptic will find themselves drawn in to pleasant conversation without complaint.
For families
A few families with small children are present during my stay, and such is the vastness of the space that they had totally free reign not at all to lone adults’ detriment. There’s also a beautiful kids’ club with daily programming from 9 a.m. to 5 p.m., plus water sports rental equipment.
John Pringle Drive, Montego Bay
Jamaica
https://www.roundhill.com/
+1 876-956-7050