Cityscape Sails on Lake Michigan with Two Brothers Sailing Chicago
Difficulty
easy
Duration
2–6 hours
Fitness Level
Suitable for all fitness levels since the sailing is managed by crew; minimal physical exertion required.
Overview
Sail along Chicago’s stunning lakefront with Two Brothers Sailing Chicago, where 2- to 6-hour charters offer unmatched views of the city skyline from Lake Michigan’s waters.
Drifter / Cityscape Sails
Available from 10:00am to 5:00pm
Select participants and date
Adventure Photos
About This Adventure
Experience the breathtaking beauty of Chicago from the water on a charter that sails from Museum Row to Navy Pier. Choose from 2 to 6-hour excursions and enjoy stunning views of the city skyline, making this a unique and memorable way to explore the Windy City.
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
Dress for Wind and Water
Layers and windproof jackets help you stay comfortable during breezy lake conditions.
Bring Sun Protection
Sunglasses, sunscreen, and hats are vital since sunlight reflects off the water.
Arrive Early for Boarding
Plan to arrive 15 minutes before your scheduled departure to ensure a smooth start.
Keep Hydrated
Even on cool days, water is important when spending hours exposed on the lake.
Local Insights
Wildlife
- Double-crested cormorants nesting along rocky outcroppings.
- Common loons occasionally visible in the deeper water near Navy Pier.
History
Chicago’s lakefront has evolved since the 19th century from industrial harbor to a recreational hub, with Navy Pier opening in 1916 as a key cultural landmark.
Conservation
Two Brothers Sailing Chicago promotes environmentally responsible practices by minimizing waste and encouraging respect for Lake Michigan’s delicate aquatic ecosystem.
Select participants and date
Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Windbreaker Jacket
Blocks cool lake winds and maintains comfort during varied spring weather.
spring specific
UV Protection Sunglasses
Reduces glare from sun reflecting off the water.
summer specific
Insulating Layer
Keeps you warm as temperatures drop in the late afternoon and along the lake.
fall specific
Water Bottle
Hydration is key during hours spent outdoors on the water.