All Sails in Chicago, IL

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.

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.

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.

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.

History comes alive on this exciting educational adventure for curious minds of all ages. Experience a hands-on sailing trip aboard Windy led by our crew-educators.

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.

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.