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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 – STARTING MAY 2025

Available 2025 Cruises

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

Architecture and Skyline Sails

Leave the hustle and bustle behind and explore Chicago’s gorgeous shores with a leisurely trip around Lake Michigan.

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.

Mondays at 7PM

Monday Night Blues Summer Concert Series

Kick off your week and join us for a 2-hour concert sail from 7pm-9pm every Monday this summer.

People Watching Fireworks Against Chicago Skyline from Tall Ship Windy at Navy Pier

Wednesdays & Saturdays

Fireworks Cruise

There is no better seat in the house to watch the show than sailing aboard 148′ Tall Ship Windy.