For the best Chicago sunset, visitors and residents alike come aboard 148′ Tall Ship Windy- the official ambassador for the City of Chicago. Departing Navy Pier at 7pm daily, you will enjoy a spectacular sailing cruise and enjoy the breathtaking moments as the sun sets gently behind the Chicago Skyline.
Browse our sails below and book your Chicago Sailing Adventure today!
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.
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.
This is the don’t miss sail of the year, Tall Ship Windy’s Labor Day End of Summer Celebration Sail. Departing from Navy Pier at 8:45pm, celebrate Labor Day, and for some the end of Summer, with your friends and family aboard the famous 148′ four-mast schooner S/V Windy.
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 20 and on Sunday, August 21, 2022.
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!