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Tall Ship Windy Memorial Day Skyline Page Background

Tall Ship Windy

Welcome Aboard Tall Ship Windy!

Tall Ship Windy, sailing from 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 to lively Chicago Architectural Tours, there is something for everyone. Enjoy the Chicago skyline as you sail on our tall ship!

Book Your Next Sail

Available Cruises

Tall Ship Windy Pirate

Sept 20, 2024

Pirates Pub

Picture this: An onboard DJ, the wind in your hair as you dance the night away and the mesmerizing Chicago skyline as your backdrop.

Navy Pier Tall Ship Windy Pirate Close Up

Daily at 1PM

Pirates and Maritime Stories

From epic battles to trickery and treasure, experience the incredible tales of real pirate adventure!

Tall Ship Windy Lake Michigan Cruise Photo

Daily at 3PM and 5PM

Architecture and Skyline Sails

Select from Pirates and Maritime Stories at 1pm, Architectural and Skyline Tours at 3pm and 5pm and Sunset and Skyline Sails at 7pm.

Tall Ship Windy Cocktail Close Up

Daily at 5PM

Happy Arr-our Chicago Architecture and Skyline Sail

It’s the perfect way to end your workday or kick off your weekend plans.

Navy Pier Tall Ship Windy Photo

Daily at 7PM

Sunset and Skyline Sail

Sit back and relax, enjoy some soothing music and gently complete your day with this dramatic sunset.

Navy Pier Tall Ship Windy Photo

Saturdays, Sundays & Mondays

Educational Sails

Share the marvel of maritime heritage on the Great Lakes as history comes alive with an exciting educational adventure for curious minds of all ages.