Experience the Chicago Skyline Sail: Tall Ship Adventure on Lake Michigan
Difficulty
moderate
Duration
2–3 hours
Fitness Level
Participants should be comfortable moving around a boat deck and standing for extended periods.
Overview
Discover the Chicago skyline like never before aboard the Windy, a stunning tall ship sailing Lake Michigan from May to October. This unique adventure blends cityscape views with classic nautical charm for an unforgettable outdoor experience.
Skyline Sail - May to Oct 1
75 Min Sail
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Adventure Photos
About This Adventure
Escape the city's hustle with a 75-minute sail on Lake Michigan, available daily from May to October. Experience Chicago's stunning skyline from the water, with themed sails including pirates, architecture, and sunset views. Each trip offers a unique perspective of the Windy City, making it a memorable adventure.
Duration
Each sail is approximately 75 minutes.
About
AVAILABLE NOW SAIL DAILY MAY THROUGH OCTOBER 1! Leave the hustle and bustle behind! Explore Chicago's 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.
- 1pm Daily: Pirates and Maritime Stories
- 3pm Daily: Architecture and Skyline Sail
- 5pm Daily: Happy Arr-our Chicago Skyline Sail
- 7pm Daily: Sunset and Skyline Sail
Beginning September 3: Enjoy a Sunset Skyline Sail at 5pm and a Late Summer Twilight Sail at 7pm
To book now, click a date to browse availability and select your preferred sail time.
Adventure Tips
Arrive Early for Best Seating
Arrive at least 20 minutes early to grab a good spot on deck for unobstructed skyline views.
Dress in Layers
Lake Michigan’s breeze can be cool even in summer evenings; layered clothing keeps you comfortable.
Bring a Camera with Zoom
Capture close-ups of architectural details and wildlife with a camera that has a good zoom lens.
Check Weather Before Heading Out
Lake conditions can change quickly; confirm the trip is running smoothly on your sailing day.
Local Insights
Wildlife
- Double-crested cormorants often seen drying wings on pilings
- Bald eagles occasionally spotted soaring above the shoreline
History
Chicago’s maritime tradition dates back to the 19th century when the Great Lakes were vital transport and trade routes.
Conservation
The operators adhere to lake protection guidelines, minimizing waste and using eco-friendly materials on board.
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Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Layered Clothing
Spring weather can be unpredictable; layers help you stay warm or cool as needed.
spring specific
Windbreaker Jacket
Protects against the lake breeze and sudden weather changes during summer sails.
summer specific
Comfortable Non-Slip Shoes
Ensures safe footing on the moving deck amid wet conditions.
fall specific
Sun Hat and Sunscreen
Essential for sun protection while exposed on the open deck.
summer specific