Explore Chicago’s scenic shores with a relaxing sail around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. Select from Pirates and Maritime Stories at 1pm, Architectural and Skyline Tour at 3pm and 5pm, and Sunset and Skyline Tour at 7pm.
Labor Day End of Summer Celebration Sail
Celebrate Labor Day and the End of Summer on Tall Ship Windy. This is THE event on Labor Day on Lake Michigan!
This is the best Labor Day celebration on Lake Michigan. Aboard the famous 148′ Tall Ship Windy, we will have a live DJ with plenty of great sing along music, drinks, complimentary rum punch and party favorites for the celebration. And, yes, we will be shooting the cannons! Once aboard Tall Ship Windy, you will have a fun and celebratory sail on Lake Michigan where you can enjoy the Chicago skyline and the gentle waves of Lake Michigan
Don’t miss this once a year event and finish Labor Day weekend with a bang!
- Adults VIP Access
- Children VIP Access
- Adults Standard
- Children Standard
With the live DJ, sing along to some great summer favorites as well as a few traditional songs of the Pirates while enjoying the spectacular scenery that is the Chicago skyline and the wonderment of Lake Michigan. 148′ Tall Ship Windy’s famous end of Labor Day Celebration Sail is an event that should not be missed.
Please arrive at least 15 minutes prior to departure. This is a 1.5 hour charter departing promptly at 8:45pm and returns to Navy Pier at 10:15pm. Guests must be 21 years of age to drink and/or purchase alcohol and must have valid identification.
You can purchase these optional items when you book:
- Trip Insurance: $8.00 per person—gives you the ability to cancel your reservation if needed and receive a full refund. This applies up to 8 hours before your scheduled sail time.
- Please note that without Trip Insurance, your ticket is non-refundable from 48 hours prior to departure. Tall Ship Windy will exchange your ticket in the event of a weather cancellation.