Separating the islands of Maui and Molokai—at little more than eight miles at its narrowest point—the Pailolo Channel is one of the windiest in the Hawaiian Islands. This means swimming and water sports in and around the channel are only for the very experienced. Some believe that Pailolo combines pai (lift) and olo’olo (shifting), while others say the name means “crazy fisherman,” in reference to the rough sea conditions. The annual Pailolo Challenge, held in September, is a 26-mile course from D.T. Fleming Beach Park on Maui to Kaunakakai Pier on Molokai—one of Hawaii’s best downwind runs.