On Saturday, May 13, 2023, Charles David Winslow of Southport passed away at Miles Memorial Hospital with loved ones by his side. David was 61.

David was born at St. Andrews Hospital in Boothbay Harbor on Dec. 19, 1961, to Eliot and Marjorie Winslow of Southport. Being the only child born into this maritime family, his birth announcement listed him as “Assistant Pilot,” and recorded his birth statistics in nautical terms such as time of launching, gross tonnage, displacement, and length on the waterline, as opposed to more traditional forms of measurement.

David attended Southport Central School through eighth grade, and Boothbay Region High School for his freshman year, until ice hockey lured him away to North Yarmouth Academy for his remaining high school years. While there, David was captain of his hockey team, where he was known to be a very strong defenseman.

David went on to attend Kimball Union Academy for a post-graduate year. It was at KUA where David found a lifelong friend in fellow hockey player and roommate Scot Barry, then of Massachusetts. David led his hockey team to a 25 and 3 record that year. Following KUA, David enrolled in New England College, mainly as he said, to play hockey. Upon receiving his end-of-year grades from college, and per his parents’ suggestion to make a better investment, David went on to obtain his captain’s license and began operating tugboats in the family business.

At the young age of 25, David became co-owner of The Portland Tugboat Company, where he began docking ships in Portland Harbor. This venture continued for ten years, at which time David chose to go out on his own, while also running the family business, Winslow Marine. David continued running this business, as well as other entities, until his passing. He often said that operating a tug and barge business was where his heart was, and he never saw himself doing any other type of work.

David was predeceased by both of his parents. At the time of his passing, he maintained a home in Falmouth and his childhood home on Southport Island. He leaves behind his life partner Lisa (Miller) Clarke and her daughters Alexandra and Nicole, whom he loved as his own; David was so proud to have them in his life. He welcomed everyone into his home and especially loved the times when the house was filled with friends.

David will be missed by many. He leaves behind cousins, numerous childhood friends like Hugh Thompson of Southport, and many who also grew up exploring the waters of Love’s Cove and the Boothbay region, as well as his working waterfront compadres around the country. David was a colorful storyteller with a sharp wit; one could always count on having fun and sharing much laughter with him. He was humble and a quiet supporter of those in need; his generosity touched the lives of many.

A private waterfront ceremony in Love’s Cove is scheduled to honor David. Friends and family are asked to gather at Robinson’s Wharf, formerly owned by the Winslow family, for a celebration of David’s life from 11:30 a.m. to 2:30 p.m. on Saturday, July 29, at which time we welcome the sharing of fond memories of David.

In his honor, and per David’s wishes, please consider a donation to: Rebuilding Together-Lincoln County, P.O. Box 22, Boothbay Harbor, ME 04538 or to an organization of your choosing.

Hall’s of Boothbay has care of the arrangements. To extend online condolences, light a candle or share a story or picture, please visit David’s Book of Memories at www.hallfuneralhomes.com