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Day & Evening Sails in Chicago, IL

Browse our sails on Chicago’s scenic Lake Michigan lakefront, and book your Windy City boat tour today!

From $59 per Person

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. Your ticket includes up to four complimentary beverages; beer, soda or water, per person.   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.

From $39 per Person

Watching Fireworks on Wed and Saturday night has become a Chicago tradition. And, there is no better seat in the house than sailing aboard 148′ Tall Ship Windy – the Official Flagship of the City of Chicago.

Order a cold drink from our bar and enjoy a thrilling fireworks performance as you sail along the stunning and iconic Chicago skyline during this special event sail.

The Wednesday Fireworks Boat Tour departs promptly at 8:45pm. The Saturday tour starts promptly at 9:15pm.

Experience a Sail on Chicago’s Lakefront and book your Windy City boat tour today!