Derek M. DiPaolo

January 22, 2026

It is with profound sadness that we must announce that Derek Michael DiPaolo unexpectedly passed away at his home in Stroudsburg, PA on January 22, 2026. Despite being born in Lancaster, PA, he spent much of his time in the Key West area as a boat captain and fisherman.

As a handsome young man with a contagious smile and a talkative personality Derek was able to easily connect with a diverse set of people. He was as comfortable working with the mechanics repairing large diesel engines as he was sitting at the helm of a luxury yacht taking and talking to millionaires on the way to the Bahamas. He was certainly blessed by the friendships and mentors his special personality created.

Derek’s parents were high school sweethearts coming of age in the early 70s, married and with a baby before any of the others in the gang. Derek was the first baby to come into this tightknit Lancaster City community, and they all smothered him with their love. This love is still being felt today and we know it is still comforting him.

As a kid barely out of the crib his grandfather Dick would kidnap him for entire weekends and Gram would spoil him with “sleck”. Derek’s dad finally had to find ways to get off work early to interdict the kidnapping so he could also spend time with him. Derek’s elementary years were spent with his grandfather Tony on the sidelines of Friday night football games or afternoons with the Diplomats. He learned early that what you see and hear in the locker room stays in the locker room. Derek had a special relationship with his grandmother Nan, as they shared the challenges of addiction. Nan was Derek’s inspiration and she never gave up on him. Nan won her battle but Derek could not.

His “uncle” Dave had him driving D8 bulldozers before he was eight, instructing Derek to “level the field” and walking away to let Derek figure it out. His “uncle” Pat taught him electronics and wiring and how to rebuild firetrucks and the experience of catching rides on private jets. Derek was exposed to many more worlds than your typical kid.

After graduating from Lancaster Catholic High School and attending college for a couple of years Derek felt a need for a more adventurous life (not a surprise based on his earlier years), drove south and ended up in Key West, where “uncle” Tim gave him a bed and a job on a construction crew building a marina. Again Derek’s friendly talkative nature captured the attention of a couple of old salts at the marina who shared the secrets of the seas with him. This was how a twenty-five year career working on the ocean as a charter and commercial captain started. Derek surpassed most of the Key West locals in his skill and knowledge on how to find and catch fish. He even earned the respect and friendship of the local Cuban Conch maritime community, which is saying a lot for a Pennsylvania kid.

Derek was not motivated by accumulating material goods but sought friendships; he was a generous and loyal person, and had a kind heart.

Derek is the son of Mary Lynn and Michael DiPaolo. His grandparents were Dick and Janet Hobday and Anthony and Jean Dockey DiPaolo.

He leaves behind a sister Diana and brother Alex. His Aunts Diane, Karen, Jill, Denise, Beth, Heather, and uncles, Rick, Steve, Kevin, Tom, Tony, Dino, Frank, and Ed all gave Derek a reason to return home. We could never get enough time with him.

“The Sea, once it casts it spell, holds one in its net of wonders forever”

A celebration of Derek’s life will be held at a future date.

Memorial contributions can be made in Derek’s memory to Lancaster Catholic High School, 650 Juliette Ave, Lancaster, PA 17601.