Captain Jennifer MacLean

As the owner and primary operator, Captain Jenn has been voted 4 times (2009-2010-2012-2016) Outstanding Sailing Instructor by the American Sailing Association. She's a certified ASA sailing instructor and currently holds a US Coast Guard 100-ton Near Coastal Master’s license with Sailing Endorsement.

She has been working as a sailing educator and charter yacht captain since 1999. She specializes in women’s, couples and youth sailing programs. She worked as a captain with the Boy Scouts of America for ten years in their live aboard sailing adventure program (Florida National High Adventure Sea Base) and has lived aboard her own boat for 18 years. She has been featured in different articles and magazines including Latitude and Attitude, La Vie Claire, Unwind, Waterfront News, Bearings and is also featured in a coffee table book called Women and the Sea.

Jenn has extensive coastal and blue-water sailing experience, including Atlantic Ocean crossings and many solo sails to the Bahamas. She has also sailed in Chesapeake Bay, St-Lawrence Seaway in Canada and the Caribbean. Jenn is fluent in French, English, and Spanish and enjoys all sorts of adventures including diving, fishing, singing, cooking and playing guitar.

Benji da Sailorman, a rescue dog from Miami, is the First Mate onboard Indian Summer 2. With thousands of logged hours at sea, Benji has extensive sailing experience - including 4 Gulf Stream crossings and some sailing in the Bahamas. He is passionately devoted to his main duties on board.
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Captain Feather Lee
Hello from Key West, Let me introduce myself, I'm Captain Feather Lee. I am a youthful 40s and have come to find my peace of paradise in the Florida Keys! I'm ASA Sailing Instructor teaching couples, families and youth the teamworking skills to have a great sailing experience
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Captain Jay Pisaro

When Captain Jay was just 7 years old, his father bought a MacGregor 22’ and they sailed on the Finger Lakes and Lake Ontario. He remembers what an awesome experience this was for him - learning together and having amazing adventures with his Dad. He went on to graduate from Rochester Institute of Technology, worked as a Mechanical Engineer and later went into designing and building homes.

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