Chicago Skyline Sunset Sail Aboard Official Flagship of Chicago 148' S/V Windy
- Live Guide
- Instant Confirmation
- E-Ticket
- 75 min












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!
Itinerary Details
Operated by: Windy of chicago Inc, DBA: Tall Ship Windy
Stop At: Navy Pier
148' Tall Ship Windy departs from historic Navy Pier, the entertainment venue in Chicago
Duration: 10 minutes
Stop At: 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.
Duration: 50 minutes
Stop At: Chicago Skyline
As you sail on Tall Ship Windy, guests will have a phenomenal view of the Chicago Skyline.
Duration: 15 minutes