The fashion designer Ralph Lauren has been visiting Jamaica for more than 20 years. In that time, he's contributed to several charities, and even bought one of the 27 villas at the Round Hill Hotel & Villas (800/972-2159 or 876/956-7050;; doubles from $420)—which is why he was the ideal candidate to update the hotel's 36-room Pineapple House. Renovated guest suites now have whitewashed wood walls, tile floors, and bamboo four-poster beds. In appreciation of his endeavors on the island, the government of Jamaica has issued a commemorative stamp (65 cents each) depicting the Renaissance man. The stamp, which also celebrates the centenary of the Jamaica Hotel Law, is available at local post offices for a limited time.
—Hillary Geronemus

Wild Boar Restaurant

Round Hill Hotel & Villas

A west shore institution, Round Hill is one of the places that put Jamaican tourism on the map. Over the years, many a famous name has slept here, from presidents and prime ministers to movie stars and professional athletes. The 36 white-on-white rooms are spread between the two-story Pineapple House overlooking the infinity pool and beach, and 27 private villas (most with their own pools) scattered among the property’s coconut, pineapple, and allspice groves. The 18th-century great house is now a luxury spa, the cocktail lounge and piano bar were designed by Ralph Lauren, and culinary maestro Martin Maginley oversees one of the best resort kitchens on the island.