Discover Chicago’s Skyline From a Sailboat

Family, Coastal, Groups, Sailing

Are you ready to discover Chicago’s skyline from a sailboat?

Enjoy stunning views of Chicago from the waters of Lake Michigan for more than one hour! With a leisurely trip around Lake Michigan, you can leave the hustle and bustle behind and explore Chicago's beautiful shores and skyline. Bring your friends and family to have this lovely experience with you!

There is no better way to see Chicago or Lake Michigan than aboard the 148-foot S/V Windy, the City of Chicago's Official Tall Ship Ambassador. Don't miss out on these scenic and educational cruises on a traditional tall ship from Chicago! Considering your schedule, our experienced crew will offer you three different tours. You can choose between the Pirates and Maritime Stories Tour at 1 p.m., the Architectural and Skyline Tour at 3 p.m. and 5 p.m., and the Sunset and Skyline Tour at 7 p.m. There are also some special days for a sailing tour.

Special National Rum Day Sails on August 16th.  Bacardi Sail at 1pm and 3pm.  Cruzan Sail at 5pm and 7pm. Come join the fun with special drinks, gifts and more! Special AANA World Congress Sail on August 12th at 7pm. Open to everyone, celebrate and say thank you to the Nurse Anesthesiologists Visiting Chicago.

1pm. Pirates and Maritime Stories :
Come onboard our main deck for "True Piracy Stories" on the Great Lakes! Experience the incredible tales of real pirate adventure that occurred right here on these magnificent inland seas, from epic battles to trickery and treasure. This Chicagoshowl is educational as well as entertaining! On this unforgettable sail, you'll also get to enjoy breathtaking views of Chicago's world-famous skyline while sailing the calm waters of Lake Michigan. This enjoyable tour has something for everyone in the family.

3 p.m. and 5 p.m. Architecture and Skyline Sail : Enjoy Stunning Views of Chicago from the Water! Leave the hustle and bustle behind and take a leisurely trip around Lake Michigan to explore Chicago's beautiful shores. Take in the world-famous skyline, enjoy spectacular views, and learn about Chicago from the water. The 3 p.m. and 5 p.m. tours focus on Chicago's history and world-famous architecture. Join us on the main deck to learn about the people, plans, and perseverance that shaped Chicago's most famous sight,and to enjoy the lively and educational narration.

7pm Sunset and Skyline Sail : Explore Lake Michigan's grandeur on board our traditional tall ship as Windy sails past the stunning lakefront Chicago skyline. Enjoy the breathtaking sunset setting over the Chicago skyline from the renowned Tall Ship Windy. A fantastic Sunset Skyline Sail for couples, families, or groups of friends.

What are you waiting for? Bring your family and friends and join us now to discover Chicago’s skyline from a sailboat in Chicago.



  • Genießt die Aussicht auf die beeindruckende Skyline der Stadt aus einer ganz neuen Perspektive;

  • Bei dieser Tour könnt ihr Orte fernab vom touristischen Trubel besuchen;

  • Schönes und geräumiges Boot, bekannt für exzellente Sicherheit und Komfort;

Nicht vergessen

  • Alle Aktivitäten auf dem Meer sind abhängig von Wind- und Wellenkonditionen. Falls es das Wetter nicht zulässt, kontaktieren wir euch um ein anderes Datum zu finden oder erstatten euer Geld zurück;

  • Detaillierte Anbieterinformationen, einschließlich der lokalen Telefonnummern und Adressen, sind auf der Buchungsbestätigung zu finden.

  • Eine leichte Jacke gegen den Wind könnte nützlich sein;


  • Perfect activity for your group of friends or family to celebrate special occasions;

  • Euer einheimischer Kapitän wird die Fahrt kommentieren;

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Discover Chicago’s Skyline From a Sailboat
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