Experience a breathtaking Chicago sunset sail on the iconic Tall Ship Windy. Enjoy live Blues music on Monday nights. Book your unforgettable evening now.
- Navy Pier - 148’ Tall Ship Windy departs from historic Navy Pier, the entertainment venue in Chicago
- Lake Michigan - Tall Ship Windy will sail from Navy Pier into Lake Michigan and at the perfect time, turn so our guests may see the glorious sunset behind the Chicago Skyline.
- Chicago Skyline - As you sail on Tall Ship Windy, guests will have a phenomenal view of the Chicago Skyline.
![](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-720x480/0f/7a/2d/10.jpg)
- On-board WiFi
- Goods and Services Tax (GST)
- Landing and/or facility fees
- On-board restrooms
- Alcoholic Beverages
- Snacks
- Gratuities
The famous Tall Ship Windy sunset sail is truly famous. Used in many world-renown photos, backdrops for special events, weddings, or just an evening out, the sunset sail aboard one of the only four-mast Schooners still in operation will not disappoint. You will enjoy a sail on Lake Michigan and at just the right moment, S/V Windy will gently turn toward the Chicago skyline for a view of our spectacular sunset. Sit back and relax, enjoy some soothing music, and gently complete your day with this dramatic sunset. ** Please note, tickets purchased for sunset sails on Monday evenings will be upgraded from our traditional 75 minute sail to our Monday Night Blues Summer Concert Series, which departs the dock at 7pm and returns at 9pm. Enjoy live Blues music and 45 extra minutes aboard beautiful Tall Ship Windy!
For a full refund, cancel at least 24 hours before the scheduled departure time.