An iconic colonial-style resort designed by Ralph Lauren.

Since the 1950’s, midcentury luminaries, Hollywood stars, and the blue-blooded political class have flocked to Lord Monson’s former sugarcane plantation in Montego Bay for a taste of secluded paradise. Jacqueline and John F. Kennedy honeymooned there; The Sound of Music’s first draft was written in one of its villas; Paul McCartney drops in like it’s his personal pied-à-terre. Today, it remains as big a draw as ever. Fashion designer Ralph Lauren is behind the breezy tropical refresh of the 27 villas—one of which he owns—that exude a West Indies sensibility. Whitewashed open-air spaces are decked out in tile and wood, with mahogany four-poster beds and brightly patterned pillows topping milky sofas in the stand-alone villas. The private pools and outdoor showers are edged by fragrant jasmine and frangipani. The 36 airy oceanfront rooms at Pineapple House, revamped by Lauren as well, are equally stylish, and feature pieces from the designer’s Home Collection. Head to The Grill restaurant for wood-fired renditions of traditional Jamaican dishes, or The Restaurant for a more elevated tasting menu from James Beard Award-winning chef Martin Maginley. Then find an open raffia stool at the cocktail bar, where black-and-white photos of the resort’s history line the walls and a piano provides the soundtrack, and order the famous double-rum punch crafted with the sugar cane spirit produced by the island’s own Appleton Estate.