Travel With Sara

Sailing On Tall Ship Windy In Chicago

Did you know that you can sail on a tall, pirate themed ship in Chicago? Windy, Chicago’s Official Tall Ship offers a fun, family experience.

Pirates on ship

Sailors board Windy off of the world famous Navy Pier. There is a ticket booth near the ship, should you need to purchase a last minute ticket. I would suggest purchasing your ticket online, so you are guaranteed a seat.

The evening myself and several friends boarded Windy, it was a beautiful evening. A few minutes into the sailing, sailors were invited to the middle of the ship to hear Pirate tales and more. Kids of all ages, listened intensely as a pirate told tales of the sea.

Pirate Storyteller

If you are wanting to sail on a tall ship, this is your opportunity. I personally chose to stay in my seat and take in the views of Lake Michigan and the Chicago skyline. You can choose to listen to the pirate tales or sit back and relax while Windy sails.

Onboard pirate ship

The pirate themed cruise is one of several themed cruises that Windy offers. From architectural tours to skyline sails, there’s a cruise for you. Sailing on a tall ship, like Windy, was fascinating to me, as I had never sailed on a ship with tall sails. I am proudly sporting my wings that I earned from flying Air Choice One into Chicago from North Iowa.

After your ship sails, be sure to explore Navy Pier and take a ride on the Centennial Wheel. The views from above are stunning. I chose to ride after I sailed on Windy, as the sun had set and the views of the skyline were out of this world.


Have you explored Chicago on Tall Ship Windy? If so, I’d love to hear which cruise you chose to take. Chicago is one of those cities that continues to amaze me. Each time I visit I see different things, as the skyline and sun offer stunning views that you simply cannot find anywhere else.

*Thank you to Windy, Chicago’s Official Tall Ship for hosting me and allowing me to experience Chicago in a new way.


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8 thoughts on “Sailing On Tall Ship Windy In Chicago

  1. mags

    That’s so fun! I’m going to Chicago for the first time in a couple of week and would love to do something like this.

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