Special Event Sails in Chicago, IL

Tall Ship Windy’s Memorial Day Start of Summer Celebration. Departing from Navy Pier at 8:45pm, celebrate Memorial Day and begin the summer with your friends and family aboard the famous 148′ four-mast schooner S/V Windy.

Watch the 2023 United States SailGP Chicago races from the water aboard Tall Ship Windy, departing from Navy Pier. Windy is spacious, with three decks: the fore deck, midship deck and aft deck for unique viewing opportunities.

Chicago’s famous 2 hour Pirates Pub Sail departs every Friday night at 9pm aboard Tall Ship Windy at Navy Pier. Yes, this is Chicago’s Famous and Only Floating Pirates Pub!

Aboard the 148 foot Tall Ship Windy, you will enjoy the merriment of days of yore. You will be able to listen and sing to the traditional songs of the Pirates while enjoying the spectacular scenery that is the Chicago skyline and the wonderment of Lake Michigan.  Chicago’s famous Pirates Pub Sail is an event that should not be missed.

Kick-off your week and join us for a 2-hour concert sail from 7pm-9pm every Monday this Summer. We’ll help you chase your Monday BLUES away 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.

The thrill of the Chicago Air & Water Show returns to the Lake Michigan lakefront this year beginning at 9AM on Saturday, August 19 and on Sunday, August 20, 2023.