The open-air cocktail bar pays homage to its celebrity guests with black-and-white photos of everyone from Bing Crosby to Paul McCartney and Michael Douglas sunbathing on the private beach. Located on Montego Bay, this old-world Caribbean getaway and its 27 villas have been a club for the Hollywood A List since the Fifties. Ralph Lauren owns Cottage 26, and in 2004 lent his considerable decorating skills to renovating the hotel’s historic Pineapple House. It now has mahogany four-poster beds, plantation-style chairs. Meanwhile JFK and Jackie (before she was “O’) honeymooned in Villa 10 and you don’t get much more 1960s royalty than that. If you are not feeling in the party mood then make like a nun and head for Villa 12, where Oscar Hammerstein started writing the Sound of Music after meeting Maria von Trapp on vacation.