Round Hill Hotel and Villas

Round Hill opened in 1953 on a 110-acre peninsula west of Montego Bay and promptly became the Caribbean retreat of mid-century glamour: Noël Coward and Oscar Hammerstein were among the original villa owners, John F. and Jacqueline Kennedy holidayed here, and the cottages have hosted an unbroken procession of the famous ever since. Crucially, the resort has resisted every temptation to grow, so the scale—a crescent of beach, a hillside of white-shuttered villas, a colonnaded great house—remains exactly as intimate as its founders intended.

The oceanfront rooms in the Pineapple House were redesigned by Ralph Lauren, a longtime habitué, in his crispest island idiom: white walls, mahogany four-posters, batik blues. Above them, the 27 privately owned villas—each individually decorated, most with pools and dedicated staff—scatter up the hillside among almond and mango trees, and taking one with family or friends is the classic Round Hill experience. The infinity pool at the point, seemingly pouring into the bay, is among the Caribbean's most photographed.

Days run on a gentle rota of beach, spa—housed in a restored eighteenth-century plantation house—tennis and long lunches under the seagrape trees, with evenings built around cocktails on the terrace and Jamaican-inflected dinners to a live band. It is unshowy, deeply loyal to its returning families, and one of the last places where the golden-age Caribbean can be experienced rather than imagined.