I have enjoyed a lot of different sailing events, from local regattas to glamorous destinations. Each had its own appeal, but once I’ve been there, done that, I rarely return because there are new places to explore. But I made an exception for the Golden Rock Regatta, a little-known Caribbean series that is held in November, featuring long-distance races to a smattering of islands: St. Maarten, St. Eustatius, St. Barths and Anguilla. Exhilarating stretches of racing during the day are followed by nightly raft-ups and casual parties. It perfectly combines the thrill of racing with the adventure of exploring a different piece of paradise each night, which has given me the opportunity to forge friendships with other “Rockers” over the years.