Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour

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Climb aboard Windy, Chicago's official Tall Ship Ambassador, and experience breathtaking views from the water on this tall ship cruise. Sail along Lake Michigan and learn about Chicago's architecture.


  • Feast your eyes on the breathtaking sights of Chicago from the waterside
  • Watch the sunset over the skyscrapers and bright lights of the Chicago skyline
  • Learn about the plans, people, and persistence that built Chicago's buildings
  • Sail on the 148-foot Tall Ship Windy, Chicago's official Tall Ship Ambassador
  • Enjoy live onboard narration and sip on a drink from the onboard bar


See the sights of Chicago from a unique waterside perspective on this tall ship tour. Sail around Lake Michigan onboard the tall ship Windy, a 148-foot traditional schooner. Choose from an architecture and history-focused tour or a sunset sail. On the Architecture and Skyline Sail, immerse yourself in Chicago's history and architecture. Take in the skyline, enjoy spectacular views, and discover the Windy City from the water. Learn about the people and plans that shaped Chicago’s most famous sights from the live onboard narration. On the Sunset and Skyline Sail, enjoy panoramic views of the sunset across the Chicago skyline in the company of friends or family. enjoy live educational narration about the sights you see with both options.


Sailing tour Live narration

Important Information

  • This tour takes place rain or shine

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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