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.
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Difficulty
easy
Duration
2–6 hours
Fitness Level
Minimal physical effort required; suitable for most visitors
Wildlife
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.
Two Brothers Sailing Chicago
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.
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.
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.
Sunscreen
Protect your skin during sunny cruises.
summer
Hat or Cap
Shield your face from the sun during the daytime sail.
summer
Windbreaker
Keep warm and comfortable if the weather turns breezy.
spring/fall
Camera/Smartphone
Capture your memorable views of Chicago from the water.