Rivera is an active sailor. As owner and skipper of the sailing vessel "Voyager", he participated in the Marion–Bermuda Cruising Yacht Race in 1985, 2005, 2011, and 2013. In 2013, his vessel finished in 12th place out of 34 finishers. He also sailed "Voyager" 1,400 miles up the Amazon river and around the world, going so far as to meet the King of Tonga on the international dateline in time for the new millennium. The adventures were chronicled in six one-hour-long specials on The Travel Channel, and some of this footage remains available on his website.