Water Activities & Sunset Sail with Two Brothers Sailing Chicago
Difficulty
easy
Duration
3–4 hours
Fitness Level
Casual physical condition suitable for all passengers
Overview
Set sail on Lake Michigan and watch Chicago's skyline light up the night with Two Brothers Sailing. Experience a luxurious overnight aboard Vagabond, blending city views and maritime serenity.
Sunset Sail & Stay
per group • 3 hours of sailing and over night stay - 15 hours total
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Adventure Photos
About This Adventure
Experience a breathtaking sunset sail against the stunning Chicago Skyline, followed by a serene overnight stay aboard the luxurious yacht, Vagabond. Enjoy the enchanting city lights as they twinkle in the night, making this a unique and memorable getaway for up to six people.
Rates
1 - 6 People
Duration
3 hours sailing and over night stay 15 hours total
About
Beautiful sunset sail with Chicago Skyline in the background, glimmering city lights once the sun goes down. Back to Montrose Harbor for a relaxing overnight stay on our luxury sailing yacht, Vagabond.
Adventure Tips
Arrive Early for Boarding
Get to the harbor at least 30 minutes before your scheduled departure for a smooth start.
Bring Layered Clothing
Evenings on the water can cool down; dress in layers for comfort.
Use Sun Protection
Apply sunscreen and wear a hat during the day to protect from UV rays.
Capture the Sunset
Don’t forget your camera or smartphone to snap breathtaking sunset shots.
Local Insights
Wildlife
- Seagulls
- Common Loons
History
The Chicago River and Lake Michigan have been vital for city development, serving as transportation and trade routes since the 19th century.
Conservation
The company emphasizes eco-friendly sailing practices, including minimal engine use and proper waste disposal, to protect Chicago's waterways.
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Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Sunscreen
Protect your skin from sun exposure during daytime sailing.
summer specific
Light Jacket or Sweater
Prepare for cooler evening temperatures near the water.
spring|fall|winter specific
Camera or Smartphone
Capture stunning sunset views and cityscapes.
Personal Water Bottle
Stay hydrated during your time on deck.