Tall Ship Windy is a historic sailing vessel that offers scenic tours of Chicago’s shoreline and architectural landmarks. Built in 1948, the Windy is a 148-foot-long traditional four-masted schooner that offers a unique and authentic sailing experience.
Tall Ship Windy offers a variety of tour options, including the Skyline Sail, which takes guests on a two-hour cruise along the lakefront to view the Chicago skyline and architectural landmarks from the water. They also offer the Sunset Sail, a romantic two-hour tour that offers stunning views of the sunset over the city, and the Pirate Adventure Cruise, which is perfect for families with young children.
In addition to their popular tours, Tall Ship Windy also offers private charters for special events such as weddings, corporate outings, and private parties.
Tall Ship Windy takes pride in providing an authentic sailing experience, with their crew dressed in traditional sailing attire and a focus on hands-on participation from guests. Visitors have the opportunity to help hoist the sails, steer the ship, and learn about the history of sailing and maritime culture.
Overall, Tall Ship Windy offers a unique and unforgettable way to experience the beauty and history of Chicago’s lakefront and skyline.
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FAQ's
What if it rains?
Typically, we sail rain or shine. It is up to the captain to decide whether to sail, postpone, or cancel. Please come dressed and prepared for an outdoor adventure.
Is the boat covered?
Three open deck areas are available for seating. A covered aft salon houses the bathroom, ship’s stores, and full bar. In the case of rain, a tarp may be placed over the main deck for the comfort of our guests. Again, please prepare for an outdoor adventure.
Are there life jackets on board?
The US Coast Guard requires that there be life jackets for every passenger. However, they are only passed out in an emergency.
Is the boat accessible to people with disabilities?
Windy is not handicap accessible. We welcome some guests with disabilities provided that the guests are able to ambulate up and down 6 steps on each side of then boarding ladder, and be escorted to a seat on the Main deck with minimal assistance. Assistive devices such as scooters, wheelchairs and rolling walkers, must be left on the dockside storage area, and may not be used on the ship while underway. Children using wheelchairs may be carried aboard by an adult in parental role with the Captain’s permission and must be seated with family or caregivers on the main deck Adults using wheelchairs may not be carried aboard..
How many people does Windy sail with?
Windy is USCG inspected to carry our capacity of 150 people.
Where do we board the boat?
Windy docks on the south side of Navy Pier just east of Chicago Shakespeare Theater and across from the Riva restaurant. Please arrive at least 30-45 minutes prior to your scheduled departure for a safety orientation and boarding.
Where do we pick up the tickets for group sales?
One person from your group must check in at the ticket booth and obtain a boarding pass for your entire group. We do not issue individual tickets to groups.




