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Our sailboat "Dragonfly" is a 37' foot long, French built Jeanneau Sun Odyssey. Unlike most sailboats, this boat is designed for comfortable cruising, with a spacious open cockpit for seating, folding table, surround bluetooth stereo system that you can play from your phone, and full galley below.  Keep your drinks cool in the fridge, no cooler necessary. The boat is equipped with glasses, plates, silverware, towels, floaties, blankets, an assortment of drinks and packaged snacks. Dragonfly is fully insured and certified every year to operate as a legal charter in the city of Chicago. We carry onboard all necessary safety equipment including USCG life jackets and your captain is first aid CPR certified.


Captain Greg Scannell is a certified USCG Master Captain and sailing instructor. He is committed to providing you a great time, keeping you safe, and helping you create positive lasting memories. Together, Greg and Cait have sailed over 10,000 miles around the country through its waterways on the Great American Loop, sailed the Bahamas for two months on Dragonfly, and have captained luxury catamarans in the Caribbean.


Cait Scannell will join charters as her schedule permits as she runs a professional solo architecture practice. When she's along she will often take the helm where she's most comfortable. Cait bought Dragonfly in 2016 after taking lessons from Greg. At the time, she was the youngest female boat owner in the Chicago Harbors. She earned the nickname "Lady Dragonfly" from Monroe Harbor tender captains. 

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