THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Spend 75 minutes on Tall Ship Windy watching the Chicago skyline recede into a band of glass and steel while Lake Michigan’s breeze fills the sails. This accessible cruise combines city views, optional sail-handling, and onboard amenities.
Spend 75 minutes on Tall Ship Windy watching the Chicago skyline recede into a band of glass and steel while Lake Michigan’s breeze fills the sails. This accessible cruise combines city views, optional sail-handling, and onboard amenities.
Book with Tall Ship Windy
Book directly with Tall Ship Windy for the best rates and real-time scheduling.
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Operated by Tall Ship Windy · Chicago, Illinois
Step aboard as the city slips aft and the wind takes the wheel. The wooden decks of Tall Ship Windy creak with a different rhythm than the streets: gulls call, Lake Michigan stretches flat and wide, and the Chicago skyline reads like a page of steel and glass pushing skyward. For 75 minutes you trade traffic noise for the slap of waves and the slow choreography of sails.
easy.
1–1.5 hours.
Light-moderate—able to climb a gangway and stand on deck for the duration; optional sail handling requires basic mobility
Most sails board from Navy Pier or a nearby downtown dock; check your booking confirmation for the specific boarding point and arrive early.
Yes—this sail is family-friendly and suitable for most ages, though children should be supervised on deck and wear appropriate footwear.
Yes—guests are often invited by the crew to help with sail handling, but participation is voluntary and guided for safety.
This ticket lists all sales final, so there is no refund for cancellations; confirm schedules before booking and contact the operator for weather or accessibility questions.
Tall Ship Windy represents Chicago’s maritime training tradition and the city’s 19th-century development as a Great Lakes port.
Operators encourage leaving no trace at boarding sites and support Great Lakes conservation efforts—avoid discarding trash overboard and respect protected shoreline habitats.
Tall Ship Windy operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
Book with Tall Ship Windy
Book directly with Tall Ship Windy for the best rates and real-time scheduling.
Reserve Now