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.
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Difficulty
easy
Duration
3–4 hours
Fitness Level
Casual physical condition suitable for all passengers
Wildlife
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.
Two Brothers Sailing Chicago
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.
Two Brothers Sailing Chicago operates private sailing charters on Lake Michigan from Chicago, Illinois. The company offers a selection of excursions aboard the yachts Vagabond and Drifter, providing small-group experiences that showcase Chicago’s skyline, Museum Row, and Navy Pier.
Trips range from two to six hours and include dedicated three-hour sunset charters that depart along the city front. Options include Vagabond Sunset Sails, Vagabond / Cityscape Sails, Sunset Sail & Stay with an overnight aboard the Vagabond for up to six people, Drifter Sunset Sails, and Drifter / Cityscape Sails. Most cityscape charters follow a route from Museum Row to Navy Pier to maximize skyline viewing and waterfront perspectives.
Two Brothers Sailing Chicago focuses on personalized private charters for small groups seeking a memorable outing on Lake Michigan. Booking information, trip durations, departure points, and specific availability are provided through the business’s reservation process. The company’s itineraries emphasize the visual highlights of Chicago’s lakeshore, including close views of the skyline at sunset and evening city lights for overnight guests.
For travelers seeking a water-level vantage of the Windy City, Two Brothers Sailing Chicago offers curated sailing experiences that combine Chicago waterfront sightseeing with the leisure of a private charter. Many charters depart from the lakefront near Museum Row, offering direct access to lakefront routes. Reservations are required and available through the company’s online booking channels, and confirmation emails are sent after booking.
Location
Chicago, IL
Operating on Lake Michigan
Tours Offered
5 Trips
Sunset, cityscape, overnight options
Trip Length
2–6 hrs
Short to extended charters available
Overnight Option
Yacht Stay
Overnight aboard Vagabond available
Reserve a sunset sail, cityscape cruise, or overnight yacht stay aboard Vagabond or Drifter — limited private charters available.
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.
Sunscreen
Protect your skin from sun exposure during daytime sailing.
summer
Light Jacket or Sweater
Prepare for cooler evening temperatures near the water.
spring|fall|winter
Camera or Smartphone
Capture stunning sunset views and cityscapes.
Personal Water Bottle
Stay hydrated during your time on deck.