Bucket Listers is excited to partner with Tall Ship Windy to offer you exclusive ticket pricing:

Skyline Sail

💰Price list:
Adult: $45.77 per person (originally $49)
Child: $36.43 (originally $39)
🗓️Multiple dates
⏰Schedule:
1:00 PM - 2:15 PM: Pirates and Maritime Stories
3:00 PM - 4:15 PM: Architecture and Skyline Sail
5:00 PM - 6:15 PM: Architecture and Skyline Sail
📍Navy Pier: 600 E Grand Ave, Chicago, IL 60611

About the event:

There’s no better place to view Chicago or Lake Michigan than aboard 148′ S/V Windy; the Official Tall Ship Ambassador for the City of Chicago. Don’t miss these scenic and educational cruises from Chicago’s famous traditional tall ship! Select from Pirates and Maritime Stories at 1:00 PM or Architectural and Skyline Tour at 3:00 PM and 5:00 PM. 

1:00 PM Sail: Pirates and Maritime Stories

Join us on our main deck for “True Stories of Piracy” on the Great Lakes! From epic battles to trickery and treasure, experience the incredible tales of real pirate adventure that happened right here on these magnificent inland seas. This Chicago sail is both educational and entertaining! On this unforgettable sail, you also get to enjoy awe-inspiring views of the world-famous skyline of the Windy City while sailing the gentle waters of Lake Michigan. There’s something for everyone in the family on this fun tour.

3:00 PM + 5:00 PM Sails: Architecture and Skyline Sail

Experience breathtaking views of Chicago from the water! Leave the hustle and bustle behind and explore Chicago’s gorgeous shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. The 3:00 PM and 5:00 PM tours feature the history of Chicago and its world-famous architecture. To learn about the people, plans, and persistence that shaped Chicago’s most famous sights, join us on the main deck and enjoy the lively and educational narration.


Pirates Pub Sail

💰Adult: $92.47 per person (originally $99) (includes one complimentary rum punch)
🗓️Friday Nights
⏰9:00 PM - 11:00 PM
📍Navy Pier: 600 E Grand Ave, Chicago, IL 60611

About the event:

Yes, this is Chicago’s famous and only floating pirates pub! The event on Navy Pier is on Friday nights for you and your friends. Aboard the 148-foot Tall Ship Windy, you will enjoy the merriment of days of yore.

You will be able to listen and sing to the traditional songs of the pirates while enjoying the spectacular scenery that is the Chicago skyline and the wonderment of Lake Michigan. Chicago’s famous Pirates Pub Sail is an event that should not be missed.

Please arrive at least 15 minutes prior to departure. This is a two-hour charter and returns to Navy Pier at 11:00 PM. Guests must be 21 years of age or older and must have valid identification.

Educational Sail: Tall Ship Discovery

💰Price list:
Adult: $27.09 per person (originally $29)
Child: $15.88 per person (originally $17)
🗓️Saturdays, Sundays, and Mondays
⏰Schedule:
11:00 AM - 12:30 PM
📍Navy Pier: 600 E Grand Ave, Chicago, IL 60611

About the event:

Ahoy! Join us for an exciting educational adventure aboard the Tall Ship Windy! Great Lakes history and maritime tradition come alive from the decks of our floating classroom.

This unique, hands-on learning experience is a great way to enjoy physics, ecology, history, and storytelling while taking an active part in sailing the vessel.



Pirates Pub Sail is a 21+ event. Our other sailing experiences are all ages.
All sales are final. No refunds or exchanges.