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 Tours at 3pm and 5pm and Sunset and Skyline Sails at 7pm.
Browse our sails on Chicago’s scenic Lake Michigan lakefront, and book your Windy City boat tour today!
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 7pm daily, you will enjoy a spectacular sailing cruise and enjoy the breathtaking moments as the sun sets gently behind the Chicago Skyline.
Sail into the night and embark on a two-hour party sail; join us for Chicago’s only Pirates Pub. Sail onboard a 148-foot Tall Ship in the Windy City! This is an event you will not want to miss. Enjoy an onboard DJ and the wind in your hair as you dance the night away with the mesmerizing Chicago skyline as your backdrop. Sing along to traditional pirate tunes and your favorite party anthems while soaking in the breathtaking sights of Lake Michigan.
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.
Experience a Sail on Chicago’s Lakefront and book your Windy City boat tour today!