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.
Browse our sails below and book your Chicago Sailing Adventure today!
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.
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.
Enjoy onboard happy hour drink specials every night at 5pm and experience breathtaking views of the Chicago skyline from the water! It’s the perfect way to end your workday or kick off your weekend plans. Learn about the people, plans and persistence that shaped Chicago’s most famous sights and join us on the main deck to enjoy the lively narration.
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.
The thrill of the Chicago Air & Water Show returns to the Lake Michigan lakefront this year on Saturday, August 17, and Sunday, August 18, 2024. Join us onboard Tall Ship Windy to enjoy 3 hours of the show from the water.
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!