For the historic 100th running of the world's longest and oldest freshwater race, the Chicago to Mackinac, the field was expanded to more than 430 boats. American Sailors takes you on board and behind the scenes as four great skippers prepare their boats, their strategy and their teams to take on the 330 mile challenge. Join Tom Giesler, the Pro, aboard Windquest, the defending champion, on one of the most beautiful and decorated boats ever to race in fresh water, John Nedeau, the Old Goat, who will guide his Great Lakes 70 ft boat Windancer for a record 61st time! Brian Torresen, the Cowboy, takes the helm for the first time aboard his tricked out 32 ft Melges called Peerless. And Steve Schiller, the School Teacher, who sails with his two sons and best buddies on his father's old boat, Souvenir, in a quest to end a 30-year dry spell.