See Chicago from the Water — Private Sailing Charters on Lake Michigan
Sunset sails, cityscape cruises, and overnight yacht stays aboard Vagabond and Drifter for small-group experiences.
Featured Sails & Charters
Choose from sunset sails, 2–6 hour cityscape cruises, and an overnight yacht stay.
About Two Brothers Sailing Chicago
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.
Book a Chicago Sailing Experience Today
Reserve a sunset sail, cityscape cruise, or overnight yacht stay aboard Vagabond or Drifter — limited private charters available.