Thank you for a great season! We're now closed. Check back for updates on our 2024 sailing season.
Thank you for another fantastic season! We’re already counting down the days until we can set sail with you again aboard Tall Ship Windy in 2024.
If you’re looking for other ways to sail, we invite you to explore our other exciting locations! Tall Ship Windy is proud to be a part of the Amphitrite Digital family of companies.
Join us at Paradise Adventures in Panama City Beach, Florida, where sun-kissed shores await. If you’re dreaming of a week-long yacht vacation, Charter Smarter in the Virgin Islands promises an unforgettable experience. For a full or half day on the water from St. Thomas and St. John in the US Virgin Islands, our team at Seas the Day Charters USVI is ready to make your dreams a reality.
No matter where your compass points, we’re here to create more unforgettable memories with you. Until then, fair winds and following seas.
Enjoy top-rated boating adventures on the Florida Gulf Coast at Paradise Adventures Catamarans and Watersports!
Explore the wonders of the Virgin Islands with an all-inclusive Charter Smarter yacht charter!
Enjoy a full or a half-day adventure with Seas the Day Charters USVI!
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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 Theme at 1pm, Architecture and Skyline at 3pm and 5pm, or Sunset and Skyline at 7pm.
75 Minutes | Starting at $39
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.
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.
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.
The Tall Ship Windy, located on Chicago’s Navy Pier, brings you exciting boat tours that are educational, creative, and inspiring. From our daily storytelling adventures and field trips for students to our concert sails, there is something for everyone. Come enjoy the Chicago skyline as you sail on our tall ship!
For groups or charters, email us at [email protected] or call us at: (312) 451-2700
The Tall Ship Windy offers the most spectacular fireworks experience during the Chicago summer.
Our sails are both fun and educational, which makes them the perfect way to see Lake Michigan.
Feel the spirit of centuries past and hoist the sails as part of your experience on Tall Ship Windy.
There is simply no better way to experience Chicago’s world-famous skyline than on the Tall Ship Windy.
We went on the "pirate" cruise. They told tales of actual Lake Michigan pirates and made it very entertaining for the kids and the adults. I want to go on this cruise again!
– Deb R., TripAdvisorWe went on the Lakeside Architecture Tour. It was a very educational and relaxing seventy-five minutes. I highly recommend the experience.
– Ron F., TripAdvisorI've set sail on Tall Ship Windy 4-5 times over the past few years, and it is always a good time. You get a nice view of the city and the crew is entertaining and knowledgeable.
– Daniel C., TripAdvisorIf you want humor, entertainment, and an inclusive experience for young and the old, don’t miss this! I appreciate everything about this adventure, and Austin you’re the best!
– Tina B., TripAdvisorHad a wonderful sail on a chilly, overcast night! Crew was professional, friendly and informative. Would recommend this trip to anyone, so relaxing. Oh, used a Groupon, an extra bonus!
– Cathy B., TripAdvisorBest view of the city! Highly recommend the 7pm sail to watch the sunset between the buildings. Fun and knowledgeable crew made the Windy the highlight of our Chicago visit.
– Lance B., TripAdvisor
