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Sailing Through History: A Voyage Aboard Tall Ship Windy in Chicago

a sunset over a body of water

Chicago, the city of architectural marvels and cultural diversity, offers visitors a unique opportunity to step back in time and experience the grandeur of maritime history. One such enchanting journey awaits aboard Tall Ship Windy, a majestic vessel that sails the waters of Lake Michigan. Join us as we embark on a virtual voyage below, exploring the charm and allure of this iconic tall ship and the rich history it carries.


Setting Sail on Tall Ship Windy:

As you step onto the deck of Tall Ship Windy, you are immediately transported to a bygone era. The ship, with its towering masts and billowing sails, exudes a sense of nostalgia that captures the imagination. Originally built as a traditional Great Lakes schooner, Windy has been meticulously restored to its former glory, providing guests with an authentic sailing experience.


Windy’s Grandeur:

Standing tall at 148 feet, Windy is a four-masted beauty that dominates the Chicago skyline when docked at Navy Pier. Its impressive rigging and intricate sails showcase the craftsmanship of a bygone era. Whether you’re an avid sailor or a first-time sea explorer, Windy embarks on an unforgettable journey through the waters of Lake Michigan.


A Floating Classroom:

Beyond its aesthetic appeal, Tall Ship Windy serves as a floating classroom, offering educational programs that delve into the maritime history of the Great Lakes. From the golden age of sail to the tales of notorious pirates, guests have the opportunity to learn about the region’s rich maritime heritage while feeling the wind in their hair.

Pirate Adventures:

For those with a sense of adventure, Windy also hosts pirate-themed cruises, turning the sailing experience into a swashbuckling escapade for the whole family. Young and old alike can learn the art of treasure hunting and enjoy interactive stories that bring the history of piracy to life on the open water.


Sunset Sails:

As the day transforms into night, Tall Ship Windy offers a blissful escape with its sunset sails. Witness the Chicago skyline bathed in the warm hues of the setting sun as you sail across the lake. It’s a perfect setting for a date night, an anniversary celebration or simply a moment of tranquility away from the bustling city.



Tall Ship Windy is not just a vessel; it’s a time machine that allows you to sail through history and experience the allure of a bygone era. Whether you’re a history enthusiast, a family looking for a unique adventure or a couple seeking a romantic getaway, Windy will take you on an unforgettable journey on the shimmering waters of Lake Michigan. So, set sail on this magnificent vessel and let the winds of history carry you away on a nautical adventure like no other.


December 15th, 2023