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All Sails in Chicago, IL

Browse our sails below and book your Chicago Sailing Adventure today!

From $79 $59 per Person
  • 2 Hours - Complimentary Beverages

Chicago’s Famous Friday Night Pirates Pub Sail

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.

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  • Most Popular!
From $29 per Person
  • 75 minutes

Chicago Skyline Sail Aboard 148' Tall Ship Windy

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. Select from Pirates and Maritime Stories at 1pm, Architectural and Skyline Tour at 3pm and 5pm, and Sunset and Skyline Tour at 7pm.

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From $49 per Person
  • 90 minutes

Fireworks Cruise! Departs Every Wed 8:45p and Saturday 9:15p

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.

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Fireworks Sails

Special Sails

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!