02The story

01

Round Hill opened in 1953 on a private peninsula outside Montego Bay, and it has been the address of a certain Jamaica ever since: 110 acres of gardens and shoreline, white rooms under the palms, villas and suites designed by Ralph Lauren and a cocktail bar named for him.

The choice is between the Pineapple House, whose 36 rooms sit on the oceanfront, and the 27 villas scattered through the grounds, from two bedrooms to six, most with a pool of their own. Days pass between the beach, the tennis courts and the spa; evenings begin at the Ralph Lauren Cocktail Bar and move to The Grill or the Seaside Terrace. It is the Jamaica of the old photographs, still in colour.

02

A peninsula of 110 acres

The estate is a peninsula to itself, 110 acres of tropical garden and shoreline outside Montego Bay, and the scale is what keeps it civilised: nothing is crowded, the beach is a walk through the gardens, and the villas sit far enough apart to be private without being remote. Tennis and pickleball courts, an open-air yoga pavilion, watersports off the beach and a glass-bottom boat give a day its options, and golf can be arranged. Since 1953 the place has been run on the understanding that guests return, and the gardens have had decades to grow into the idea.

03

Pineapple House or a villa

The Pineapple House holds the 36 oceanfront guest rooms and the five suites, in white walls and windows full of sea and palm. The 27 villas are the other Round Hill, two to six bedrooms each, most with private pools, spread through the gardens so that a family or a house party can keep its own hours; Ralph Lauren designed the villas and suites, and his island register runs through them. The rooms suit a week at the water; the villas suit a household. Either way the light is white and the palms are close enough to hear.

04

Cocktails at the Ralph Lauren Bar

Evenings at Round Hill have a shape. They start at the Ralph Lauren Cocktail Bar, which is dressier than the day has been, and move on to The Grill or the Seaside Terrace, with the water black beyond the tables. The Georgian Room and the Hanover Terrace widen the choice, the Round Hill Bar and the Pool Bar loosen it. By day the spa keeps to its own pace and the yoga pavilion opens early to the sea air. None of it is new, which is the point: Round Hill understands its own history and dresses for it.

03Highlights

What sets it apart.

The signature moment

Half past six at the Ralph Lauren Cocktail Bar. The sea has gone to silver, the palms to silhouette, and a rum punch arrives with the first of the lights coming on along the peninsula. Somewhere in the gardens a villa is hosting its own party. Dinner at The Grill is at eight, and there is no hurry at all.

01Private peninsula since 1953
02110 acres of gardens and shoreline
0336 oceanfront Pineapple House rooms
0427 villas, two to six bedrooms
05The Ralph Lauren Cocktail Bar

04The Set by Invitation

Here, as a preferred guest.

01
Breakfast for two, every morning
Breakfast for two each morning, at the hotel’s own table: the first privilege of the day and the one most worth taking slowly.Breakfast on Regent Street, beside the river or on the sand, however the day is planned.
02
A hotel credit to spend
A credit held in your name at the hotel, to spend as the stay suggests: a table, a treatment, an evening at the bar.A credit for the spa, the pool bar or dinner, in the manner of the house.
03
A room above your booking
An upgrade to the category above, so the room you return to each evening outranks the one on the confirmation.An upgrade, in Bangkok towards the courtyard suites, on Siargao towards the larger villas.
04
An earlier arrival
Check-in before the house’s usual hour: the overnight flight lands, the car draws up and the first day begins in your room.The room ready early, so a dawn arrival in Bangkok or London begins upstairs.
05
A later departure
Check-out after the house’s usual hour, so the last morning is spent as the first was: at the table, by the pool or simply in the room.The last morning kept for the pool, the pier or one more hour of Soho.
06
Known before you arrive
VIP recognition as a guest of the house: your preferences and the occasion known to the hotel before the door is opened for you.The Set’s liaison and VIP desk place your occasion and preferences with the hotel in advance.
07
Offers for preferred guests
The offers a programme keeps for its own preferred guests, extended to a Dip Needle booking and shown beside the rate for your dates.By Invitation offers for your address and dates, set beside the rate in the proposal.