Adventure Brief
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.
2–6 hours
easy
Family Friendly
No Experience Required
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.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
2–6 hours
Fitness Level
Suitable for all fitness levels since the sailing is managed by crew; minimal physical exertion required.
Wildlife
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.
Two Brothers Sailing Chicago
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.
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.
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.
Windbreaker Jacket
Blocks cool lake winds and maintains comfort during varied spring weather.
spring
UV Protection Sunglasses
Reduces glare from sun reflecting off the water.
summer
Insulating Layer
Keeps you warm as temperatures drop in the late afternoon and along the lake.
fall
Water Bottle
Hydration is key during hours spent outdoors on the water.