Tall Ship Windy

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Departing from Chicago’s famed Navy Pier, Tall Ship Windy offers visitors a unique view of the city skyline alongside the excitement of sailing a real, authentic Tall Ship. With several tour options to choose from as well as chartered trips and events, there is a lot to do aboard Tall Ship Windy during the summer months.

About the Ship

Tall Ship Windy is a 148-foot, four-masted, gaff topsail schooner. Though she is a modern vessel built with some of the best-made modern materials, Windy is modeled after schooners from the 19th century’s Golden Age of Sail.

Built in 1996, Windy was designed by Capt. Robert “Bob” Marthai and brought to Lake Michigan in July of that year. She was immediately welcomed by the Chicago community as the largest schooner to sail the lake. Her mission to bring the job of Tall Ship sailing to the general public was also well recieved. As a modernly built ship, Windy sports all the benefit of modern day amenities such as pasteurized plumbing, a 300hp diesel engine, and bow thrusters for docking while still maintaining the authenticity of real Tall Ship sailing in her design.

From the start, Windy was dedicated to spreading the love of sailing to a modern audience. As such, she has been used for recreation as well as education since coming to Chicago in 1996. Hosting scouts, families, youth groups, and visitors as well as hosting festivals and celebration has endeared Windy to the people of Chicago in a unique way. As such, former Chicago mayor Richard M. Daley gave Windy the prestigious title of the official flagship of the City of Chicago in 2006.

Main Attraction

Tall Ship Windy is one of two ships owned and operated by Tall Ship Adventures of Chicago, a small business owned by locals Capt. Bruce and Karen Randall since 2008. The couple owns both Tall Ship Windy and sister ship Pianissimo. They offer both tours and charter options on Lake Michigan throughout the warmer months in the area.

There are several tour options which range from 60 minutes to 3 hours long and more. Popular choices are the Real Pirates of the Inland Seas, Arrrrchitecture Cruise, and Spirit Ships & Haunted Harbors. Additional options offered by Tall Ship Adventures include catered events, picnics, BBQs, and even weddings.

Why It’s a Must-See

Though rides on Tall Ship Windy are only available on a seasonal basis, they offer visitors to the city of Chicago a truly unique way to view the skyline and learn about the area. With the appeal of a small business and the glamour that comes from being the city’s flagship, Windy offers people from all places an authentic sailing experience that is uniquely Chicagoan.

Where to Buy It

There are a number of ways you can enjoy admission to this attraction.

Save up to 20% online at Smart Destinations. If you add more than one attraction to the cart, you will get an automatic savings of up to 20%. It’s called Make Your Own Pass.

Pay Full Price and purchase a ticket from Tall Ship Windy either online or in person.

Purchase a Tourist pass. Tall Ship Windy is available on the Go Chicago Card.