Explore Chicago’s scenic shores with a relaxing sail around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water.
Browse our sails below and book your Chicago Sailing Adventure today!
Are you looking for a relaxing sail along the Lake Michigan lakefront? Are you interested in an educational tour featuring stories from Chicago’s unique history? Or maybe you would prefer to enjoy a drink or two while watching a thrilling fireworks display over the stunning Chicago skyline? Let Tall Ship Windy be your guide!