OVER 400 PRIVATE CHARTERS IN CHICAGO SINCE 2018
This 3-hour sailboat cruise will take you & your guests on a favorable sail down the gorgeous coastline of Chicago's lakeshore, giving a unique perspective on the city's world-class architectural landscape. If you're looking for a private & intimate sailing experience Chicago - this is the cruise for you.
Starting at $899 for 6 guests
Relax and enjoy a captained sunset cruise on our sailing yacht, a Jeanneau Sun Odyssey 37. We will cast off from Monroe Harbor in downtown Chicago and set sail to a favorable course on Lake Michigan. Bring your own food and drinks, listen to your favorite music, and take in the views of our city’s iconic skyline from the Lakefront.
Starting at $899 for 6 guests
Chicago's famous lakefront party is back. This 4-hour private sailboat charter is designed for you & your friends to party in luxury. We will depart from Monroe Harbor, anchoring the boat in the party zone. Whatever you do - don't forget a bathing suit, some sunscreen & something cold to sip on!
Starting at $1,099 for 6 guests
This 2.5 hour Chicago sailboat cruise will split your time us between sailing the city's famous Lakefront & eventually making our way to the famous Fireworks show at Navy Pier. These are the best seats you can possible have for a world-class fireworks show. We've all seen fireworks - you've never seen anything like this before.
Starting at $799 for 6 guests
“I rented [Dragonfly] to celebrate my bday with 6 close girlfriends. Greg was very communicative before the trip. He answered all my questions in a very timely manner. The boat is very spacious!
Dyna, Chicago, IL
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