The Chicago Yacht Club is proud to have a longstanding tradition of yachting excellence. The Club's most famous event is the Chicago Yacht Club Race to Mackinac, which is the longest annual freshwater sailing race in the world. Boats will pass under the Mackinac Bridge in Mackinaw City heading East. Perfect view from area hotels like Best Western Dockside, Hamilton Inn Select and Clarion Hotels in Mackinaw City.