MONTEGO BAY, Jamaica — Celebrating its 60th anniversary this year, Round Hill Hotel & Villas epitomizes an era in Jamaican tourism when relaxation and glamour went hand in hand. Set on the grounds of a former sugar plantation about 10 miles west of clamorous Montego Bay, Round Hill was built as a private resort community and is not averse to a little name-dropping. A-list shareholders and their guests have included Noel Coward, Cole Porter, Grace Kelly, and Jacqueline Kennedy. Ralph Lauren renovated and designed the accommodations in the Pineapple House, a 36-room oceanfront hotel. But for a true immersion in the Caribbean lifestyle, choose a suite in one of the 27 private villas. The air-conditioned bedroom and bath are almost an afterthought since daily life takes place in an open-air living space for eating, reading (and for the misguided, even working) and a semiprivate pool for lounging. On an island where mega-resorts rule, Round Hill demonstrates that the true essence of luxury is understatement. Hotel rooms from $329, villa rooms from $349.
ROUND HILL HOTEL & VILLAS John Pringle Drive, Montego Bay, Jamaica, 800-972-2159, www.roundhill.com