Day & Evening Sails in Chicago, IL

Take a relaxing sail along Chicago’s shoreline and enjoy breathtaking views of the skyline. Available daily, with special sunset and twilight options starting in September.

Set sail for a magical evening and watch Navy Pier’s fireworks light up the sky! Enjoy stunning skyline views, a relaxing sail, and a drink from our onboard bar.

Experience Chicago’s Air & Water Show from the Best Seat on the Lake! Great for friends & family!

Sail into Independence Day aboard Chicago’s Official Tall Ship Windy! Enjoy patriotic music, stunning skyline views, and a festive evening on the water.

Join us for a beautiful evening of blues music aboard the Tall Ship Windy on Lake Michigan, featuring talented artists like Grammy Elected Michael Charles.