Tall Ship Windy

Leave the hustle and bustle behind! Explore Chicago’s shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from the water.

We’ll help you chase your “Monday blues”, aboard the 148-foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake Michigan accompanied by the sweet sounds of the blues.

Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in town! Grab a cool drink from our bar, relax, and enjoy a leisurely evening sail past the brilliant and beautiful Chicago skyline.

Chicago’s Fourth of July celebration is one of the best in the nation. Enjoying this event from Chicago’s official Schooner, Tall Ship Windy, this is truly a VIP event. This event sells-out early.

An experience you don’t want to miss! Chicago’s famous Air and Water Show aboard the 148′ Tall Ship Windy is truly a magical event.

Enjoy the beautiful Chicago lakefront and skyline from your favorite tall ship throughout our sailing season. Valid for Skyline Sails ONLY. Not redeemable any Special Event Sail.