Naples was established by Louisville Courier- Journal owner Walter Haldeman. The sister of President Grover Cleveland was one of the first to build a beach house, in what’s now called Old Naples, but she wasn’t the last to appreciate the sun and sophistication. Even into the 1930s there wasn’t much going, but there was one popular club—Club 41—where celebrities like Gloria Swanson and Gary Cooper would sometimes hang out. It’s not a place for stargazing, the privileged come here to get out of the public eye, but the list of part-time residents includes Mike Ditka, Jane Seymour, astronaut Michael Collins and Dick Gephardt. You’re most likely to see celebrities during the winter “season,” when the town is full and buzzing, but the summer brings better rates and great beach days with an even slower pace.