Background photo by Greg Hinson

Dan Wolf

State Senator, Cape Air Co-Founder

Dan Cutrona

My family has always had Cape connections. My parents bought a house on Pleasant Bay in 1965 and they owned it for 35 years practically. There are a lot of family memories in Chatham. I’m a sailor, I grew up sailing on Pleasant Bay, and I have a lot of memories out on the waters near Chatham, Orleans, Harwich—even Brewster has a little slice of Pleasant Bay . . . Even before that, my family rented a place on Lewis Bay in Hyannis, back when JFK was president. I have some really fond memories of sailing around Lewis Bay with the Kennedy sailboats out there and the Secret Service following them around. It’s an amazing place from a history standpoint.

• • •

Flying was a childhood dream and fantasy for me. I was the little kid who stood at the airport fence, watching the airplanes come and go. 

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Jeff is the Managing Editor for Cape Cod Life Publications.

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Wychmere Harbor, Harwich