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Chicago Skyline Sail Aboard 148' Tall Ship Windy

Quick Details

Experience breathtaking views of Chicago from the waters of Lake Michigan! Leave the hustle and bustle behind and explore Chicago’s gorgeous shores and skyline with a leisurely trip around Lake Michigan.

Standard Boarding
Adult Ages 13+
Child Ages 0-12
VIP Captains Boarding
Adult Ages 13+
Child Ages 0-12

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 a Chicago’s famous traditional tall ship! Select from Pirates and Maritime Stories at 1pm, Architectural and Skyline Tour at 3pm and 5pm, and Sunset and Skyline Tour at 7pm.


Experience The Beautiful Chicago Lakefront With Three Sailing Options

Tall Ship Windy offers three exciting ways to enjoy the Chicago lakefront and skyline. Scroll down to learn more about our Skyline sails and book today!

1pm. Pirates and Maritime Stories

Join us on our main deck for “True Stories of Piracy” on the Great Lakes and Caribbean! 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.

3pm and 5pm. 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 3pm and 5pm 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.

7pm Sunset and Skyline Sail

Head out on our traditional tall ship and explore the Majesty of Lake Michigan while Windy sails across our beautiful lakefront Chicago skyline. From the world famous Tall Ship Windy, experience the phenomenal sun setting across the Chicago Skyline.  A perfect Sunset Skyline Sail for individuals, family or friends.

Private Charters

Please visit our private charters page for more info or download our charters fact sheet here.