Water Activities with Vagabond / Cityscape Sails in Chicago
Difficulty
easy
Duration
2–6 hours
Fitness Level
Minimal physical effort required; suitable for most visitors
Overview
Discover Chicago from Lake Michigan aboard Vagabond / Cityscape Sails, blending breathtaking cityscape views with the tranquility of the water. Perfect for a memorable day on the lake.
Vagabond / Cityscape Sails
Available from 10:00am to 5:00pm
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Adventure Photos
About This Adventure
Experience the stunning beauty of Chicago from the water on a memorable sailing charter. Choose from 2 to 6-hour trips that glide along the city front, showcasing iconic landmarks from Museum Row to Navy Pier. Enjoy a unique perspective of the Windy City against the backdrop of Lake Michigan.
Rates
Charters starting at $400
Duration
2 to 6 hour charters available
About
See the beautiful sights – Sail the city front from Museum Row to Navy Pier as you view Chicago from the best angle: the waters of Lake Michigan.
Adventure Tips
Book in advance for sunset trips
Sunset sails are popular and fill up quickly, so reserve early to secure your spot.
Wear comfortable clothing
Layer up as it can be cooler on the water, especially during evening cruises.
Bring your camera
Capture stunning photos of Chicago’s skyline from the water at golden hour.
Check weather forecast
Wind and weather conditions can change quickly on Lake Michigan; plan accordingly.
Local Insights
Wildlife
- Seagulls
- White ducks
History
Lake Michigan has been a vital transportation route since the city’s founding, influencing Chicago’s development into a port city.
Conservation
Vagabond / Cityscape Sails follows eco-friendly practices by minimizing waste and using sustainable sailing techniques where possible.
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Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Sunscreen
Protect your skin during sunny cruises.
summer specific
Hat or Cap
Shield your face from the sun during the daytime sail.
summer specific
Windbreaker
Keep warm and comfortable if the weather turns breezy.
spring/fall specific
Camera/Smartphone
Capture your memorable views of Chicago from the water.