Day & Evening Sails in Chicago, IL

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, Sunset and Skyline Sail at 5pm and Late Summer Twilight Sail at 7pm.

For the best Chicago sunset, visitors and residents alike, join us aboard 148′ Tall Ship Windy – the official ambassador for the City of Chicago. Departing Navy Pier at 5pm daily, you will enjoy a spectacular sailing cruise and enjoy the breathtaking moments as the sun sets gently behind the Chicago Skyline.

Chicago’s famous 2 hour Pirates Pub Sail departs every Friday night at 8:45pm 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.

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 from Navy Pier has become a Chicago tradition. And, there is no better seat in the house to watch the show 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.