Chicago Skyline Tall Ship Sail

Enjoy a Relaxing Sail on a Tall Ship From Chicago's Navy Pier

1 Participant Included - Add More?

About This Experience

General Information hide

Relax and enjoy one of the most exciting sailing experiences in Chicago, a Sailing Adventure in the Windy City on the 148’ four-mast Tall Ship WINDY. Built of modern materials, but like the old trading schooners and sail training ships, the WINDY has all the character and charm of the great days of sailing. 

You may choose to help by raising and trimming the sails, or even taking a turn at the wheel. There are no set courses; as authentic sailing ships, the WINDY sails with the wind so every cruise is unique. She is silently pushed by the winds once her sails are set and engine turned off.

From the water, Chicago’s magnificent skyline is second to none and the Captain and Crew are always willing to point out the skyline landmarks and Great Lakes wildlife. So set sail and enjoy a Chicago adventure as you experience the waters of Lake Michigan!

Where It's Located hide

  • Chicago, Illinois

Who Is Included hide

The Chicago Skyline Tall Ship Sail Experience Gifts Certificate is valid for one participant, unless additional participants are added onto the certificate. There may be up to a 100 additional participants on the cruise.

This experience is not suitable for non-paying guests.

When It Is Offered hide

The Tall Ship Sails of Chicago are typically offered seven days a week May to August, subject to availability.

How Long Is It hide

The Chicago Skyline Sails have a sail time of 1¼ with a total duration of approximately 2 hours.

Weather hide

The Chicago Tall Ship Sails take place in most weather conditions but may be rescheduled by the Captain due to high winds, heavy rain, fog or other inclement weather.

What To Wear hide

Dress comfortably, layers and flat rubber-soled shoes are recommended for this sailing adventure. You may want to bring a light jacket as temperatures are cooler on the water.

Additional Information hide

The Chicago Skyline Tall Ship Sail takes place on a custom designed 148' Tall Ship which accommodates 150 passengers and was built to U.S. Coast Guard requirements. The WINDY has be designated as Chicago's Official Tall Ship Ambassador!

The ship is equipped with all of the latest life saving equipment, including life jackets, life rafts, and ship-to-shore radio. There is a small concession stand as well as clean men's and women's restrooms are available on board.

There is a full bar on the Ship with selected packaged light snacks and drinks available to purchse, as well as a gift store.

Gratuity for the Captain and Crew are not included and may be extended at the end of your sail.


Inquire about this Experience

Reservation Information hide

Changes to reservations for the Chicago Skyline Tall Ship Sail Experience cannot be made once the date of this Experience is reserved.

Xperience Certificates® cannot be exchanged once a reservation for the experience has been made.

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