Special Event Sails in Chicago, IL

A one day, VIP event.  Moonlight Sail Aboard Tall Ship Windy.

Tall Ship Windy’s Memorial Day Start of Summer Celebration. Departing from Navy Pier on Sunday May 26th at 8:45pm, celebrate Memorial Day and begin the summer with your friends and family aboard the famous 148′ four-mast schooner S/V Windy.

Sailing Lake Michigan aboard Chicago’s official flagship Tall Ship Windy is a Chicago tradition.  Enjoying a night time sail and experiencing a moonlit Chicago skyline is truly phenomenal.  Join us for this special, one day only Memorial Day sail.  And, bring your camera!

There is something special about sailing in Chicago combined by kicking off your week and joining us for a 2-hour concert sail. This Navy Pier boat tour sails from 7pm-9pm every Monday this summer. We’ll help you chase your Monday BLUES away aboard the 148-foot Tall Ship Windy as you enjoy the breathtaking views of Chicago at sunset from the waters of Lake Michigan, accompanied by the sweet sounds of the blues.

Enjoy happy hour drink specials onboard this Navy Pier Boat Tour every night at 5pm and experience breathtaking views of the Chicago skyline from the water! It’s the perfect way to end your workday or kick off your weekend plans. Learn about the people, plans and persistence that shaped Chicago’s most famous sights and join us on the main deck to enjoy the lively narration and an Architectural Tour of Chicago from the water.

Set sail on Tall Ship Windy under the nearly full moon! Enjoy a peaceful Lake Michigan evening with stunning views of the moon rising and Chicago’s glowing skyline. Each Full Moon Sail is timed for when 99% of the moon is visible. Space is limited—reserve early!

The thrill of the Chicago Air & Water Show returns to the Lake Michigan lakefront this year on Saturday, August 10, and Sunday, August 11, 2024. Join us onboard Tall Ship Windy to enjoy a 2 hour or 2.5 hours of the show from the water.

A SPECIAL EVENT SAIL! Treat yourself to an Independence Day Sail from the best seat in town!

Order a cool drink from our bar, then relax and enjoy a leisurely evening listening to patriotic music and enjoying the Chicago skyline. The City of Chicago MAY also have fireworks on July 4th, but officially this has not been announced. Chicago’s Fourth of July celebration is one of the best in the nation. Enjoying this event from Chicago’s official Schooner, Tall Ship Windy, is truly a VIP event. This event sells-out early.