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 activity.

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 activity.

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

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.

Windy is USCG inspected to carry to our capacity of 150.

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.

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.

Seating is first come, first served. Sections or seats are never reserved for groups. We cannot guarantee that your group will all be seated together.

There is a full bar in the aft salon of Windy with selected packaged light snacks, drinks, and gift store.

Visit for more info.


Payment due dates are reflected in the “charges” section of your contract. Payment is due in full at time of reservation, unless other terms are agreed to.

Reservations are completed with a payment.

Refunds are not given for unused tickets. A credit will be applied to the contact information for the group and can be used toward a future group booking.

Additional tickets may be purchased at the contracted rate on site. However, those seats are based on availability.