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.
More ways to explore the area's outdoor wonders
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.
Difficulty
easy
Duration
1–1.5 hours
Fitness Level
Light-moderate—able to climb a gangway and stand on deck for the duration; optional sail handling requires basic mobility
Wildlife
History
Tall Ship Windy represents Chicago’s maritime training tradition and the city’s 19th-century development as a Great Lakes port.
Conservation
Operators encourage leaving no trace at boarding sites and support Great Lakes conservation efforts—avoid discarding trash overboard and respect protected shoreline habitats.
Reserve your spot on the Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail" today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Arrive 20 minutes early
Boarding can be staggered and the gangway may be narrow; arriving early avoids last-minute crowds and gives time to find seating.
Dress in layers
Lake breezes can be much colder than on land—bring a windproof layer even on warm days.
Bring seasickness remedies
Though Lake Michigan’s swells are usually mild, anyone prone to motion sickness should take precautions ahead of the cruise.
Secure small items
Cameras and phones can slip on wet decks; use straps or pockets to keep valuables safe.
Windproof jacket
Blocks lake breeze and keeps you comfortable on open water.
spring
Non-slip shoes
Flat, closed-toe shoes help maintain footing on deck.
Sunglasses with strap
Reduces glare off the water and prevents dropped lenses in the wind.
summer
Motion-sickness tablets
Provides peace of mind for those prone to nausea on the water.