Round Hill, Jamaica

In short… A timeless community on Jamaica’s north shore that has been sustained by families for generations. 

The vibe… Round Hill’s unique agreement, in which the owners “share” their cottages for most of the year, makes a stay feel less like a hotel than as if a chic family friend opened up their perfectly decorated island villa. A sense of ownership, pride and connection to the community that gives Round Hill its charming personality is palpable from the moment you set foot inside the open-air lobby, where Kingsley, the legendary concierge, has been welcoming guests for more than 45 years. Many of them feed the property’s legend—the walls are lined with images of notable visitors and residents such as Ralph Lauren, Paul McCartney, Grace Kelly, Paul Newman and Babe Paley. Oscar Hammerstein wrote “The Sound of Music” in Villa 12, and JFK famously rehearsed his inaugural speech poolside at Villa 25. But while guests—boldfaced and not—mingle together over afternoon tea, for the most part, a stay here is utterly low-key, with days spent in chaises along the sandy cove, playing tennis or sailing, or by your own villa’s pool in the blithe laxity of a Slim Aarons photograph.

The rooms… Each cottage reflects its owner’s personal style, with shared proclivities for striped awnings, bougainvillea, exposed mahogany, brass fixtures and other nostalgic period hallmarks. 

The food and drink… A dining highlight was fresh mahi-mahi, caught that day by a generous guest at a neighboring dinner table and prepared by the resort’s chef. You’ll leave with jars of Round Hill’s very own tomato tapenade and their signature crispy plantain chips. 

The wellness… The journey to the spa requires a remarkable stroll along paths carved into the rocky shoreline, separating lush jungle and blue sea. 

Extra tip goes to… Kingsley Blake served as Round Hill’s legendary concierge for more than four decades. Now, he embodies the spirit of Round Hill as its ambassador, beloved by all for his warm hospitality and smiles. 

Be sure to… Visit the Rasta Village in Montego Bay and make bammy, a traditional Jamaican cassava flatbread. 

Parting words… One love.

Date of stay… December 2019