Tall Ship Windy in Chicago, IL

600 E Grand AveChicago, IL 60611
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One of the best ways to see Lake Michigan and the Chicago city skyline, Tall Ship Windy takes guests on a leisurely cruise on the water. Sailing from the Navy Pier, guests can anticipate breathtaking views on the 148-foot traditional four-masted gaff topsail schooner. With three spacious decks with seating, passengers can sit back, relax, and take in the views on this 75-minute tour.

1 or more people

Good To Know

from Ashley, one of our Chicago Travel Experts
  • Sails from Navy Pier in Chicago.
  • Ship sails rain or shine.
  • Well suited for families, and people of all ages.
  • Children must be accompanied by an adult.
  • Take in the world-famous Chicago skyline and enjoy spectacular views.
  • Explore Chicago's shores with a leisurely trip around Lake Michigan.
  • Tour duration 75 to 90 minutes depending upon the tour selected.
  • Not wheelchair accessible.


from Tall Ship Windy
Since 1996, Tall Ship Windy has been sailing from Navy Pier in Chicago and has hosted thousands of happy sailors since. Feel the spirit of centuries past and hoist the sails as part of your experience on Tall Ship Windy.

Our sails are both fun and educational, which makes them the perfect way to see Lake Michigan. There’s just no way to see Chicago’s world-famous skyline than on the Tall Ship Windy.

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Frequently Asked Questions about Tall Ship Windy

Where is Tall Ship Windy located?
The ship is located on Navy Pier, and is docked about halfway down the pier on the South dock. Look for our masts or our ticket booth.

What if it rains?
The ship typically sails 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 activity.

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 guests' comfort. Again, please prepare for an outdoor adventure activity.

Are there life jackets on board?
The US Coast Guard requires that there are life jackets for every passenger. However, they are only passed out in an emergency.

Is the boat accessible to people with disabilities?
To board the vessel, passengers must be able to descend six stairs of normal size. Items brought aboard may be left at the dock or folded and stowed in the aft salon for the duration of the sail. Pregnant women may sail at their discretion.

How many people does Windy sail with?
Windy is USCG inspected to carry to our capacity of 150.

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.

Can our group sit together?
Seating is first-come, first-served. The venue cannot guarantee that your party will all be seated together.

Is there food or drink on board?
There is a full bar in the aft salon of Windy with selected packaged light snacks, drinks, and a gift store.