Chicago’s views are notable no matter where you see them from, but taking advantage of the opportunity to see Chicago from Lake Michigan is a fascinating experience for locals and visitors alike! Sailing from Navy Pier since 1996, Tall Ship Windy has hosted thousands of happy sailors throughout summers in Chicago.
Tall Ship Windy is the first certified, four-masted traditional sailing vessel to have been built in the USA since 1921. Its character is particularly unique as the tall sails are reminiscent of pirate ship adventures from days long ago. This majestic 148-foot, four-masted schooner is built of modern materials and offers modern amenities, but still retains all of the important character from the past.
In 2006, Windy was awarded the honorable status of official flagship of the City of Chicago, by Mayor Richard Daley. Ideal for educational groups, families, history buffs, romantics, and even just friends hanging out, Tall Ship Windy is certified for up to 150 persons throughout its three large decks. For overnight chartering purposes, Windy is capable of accommodating up to 36 people in 12 cabins.
Types of Tall Ship Windy Tours
On-the-water boat tours of Lake Michigan are offered by Tall Ship Windy throughout the warmer months. Options that guests can choose for sailing tours may include architecture boat tours, city skyline tours, and even educational tours about Lake Michigan (taught by pirates!).
Special events offered may vary from season to season, but some of the favorites to experience with Tall Ship Windy are fireworks cruises as well as jazz music cruises. These special and unique events are typically scheduled for weekends and special occasions. Visitors should check the company website for details.
Tall Ship Windy may also be chartered for private events including weddings, corporate or family groups.
What You’ll See on a Tall Ship Windy Tour
Tall Ship Windy cruises allow for an uncompromised view of Chicago’s world-famous skyline such as:
- Willis Tower (formerly Sears Tower)
- The Prudential Building
- Smurfit Stone Building
- John Hancock Center
- Navy Pier Ferris Wheel
- and much more!
Tall Ship Windy Services
Tall Ship Windy offers standard service for public tours accommodating up to 150 people on a leisurely 1+ hour cruise of Lake Michigan.
Private charter cruises are also an option for the use of Tall Ship Windy for events such as weddings, team building, corporate functions, family reunions, parties and more.
Tall Ship Windy Timing
Chicago’s weather means that boat cruises are usually best left for the summertime. Tall Ship Windy’s season typically sets sail daily in May, June, July, August in the afternoons and evenings. April and September both have a limited schedule—guests should check with the tour company before making plans.
Most tours with Tall Ship Windy last for one hour and 15 minutes, but visitors should be sure to ask for the exact time when booking.
Tall Ship Windy Considerations
Answers to questions that you might not have thought to ask:
- Money Saving Tip: If you are planning on visiting several tourist attractions during your visit to Chicago, you might think about a tourist pass such as the Go Chicago Pass or Chicago Explorer Pass, both include the a tour on the Tall Ship Windy.
- Guests must arrive at least 30-45 minutes prior to their scheduled time of departure in order to avoid forfeiture of the cruise. The time ahead will be used for safety orientation and boarding the vessel so that it can sail on time.
- The Windy sails rain or shine. Tour guests should dress appropriately for the weather.
- In case of seriously inclement weather that is not appropriate for sailing, the captain may postpone the trip for up to 2 hours. If the sail must be cancelled, tickets may be exchanged for a later date (however, no refunds are allowed).
- Three open decks are available of seating and a covered aft salon houses a full bar, gift shop, and bathroom. Seating is first-come, first-served and cannot be reserved.
- Life jackets for every passenger are available in case of an emergency.
- In order to board, passengers must be able to descend six stairs, making Tall Ship Windy accessible to those with some disabilities, based on specific needs.
- Groups larger than 20 may be eligible for discounts, so be sure to ask when scheduling by phone.
- Tall Ship Windy can be seen in dock about halfway down the pier on the South Dock. The ticket booth is located at 600 East Grand Avenue, Chicago IL 60611.
A trip to Navy Pier may also be combined with a sightseeing bus line such as American Sightseeing, Gray Line Chicago, and Chicago Trolley Company.
Book a Tall Ship Windy Cruise
Tickets for Tall Ship Windy must be purchased in advance online. Tours often sell out. Booking is easy online. Online bookings show weekly availability including tour times as well as revealing tours that are already sold out. Pay for your tour in advance with a credit card and receive an email with all of the information you need about where and when tours meet as well as what to expect.