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I don’t remember him asking, but my grandpa and I both knew he would be my first passenger.
Stuart Sherman was born in 1939 in Brooklyn, New York. During his successful career as a corporate lawyer with New York Telephone Co., my grandpa became a prolific boater, often voyaging along the south shore of Long Island with my grandma, father, and aunt. Like a pilot growing from a Cessna 172 to a Beechcraft Premier, he worked his way up to a 35-foot, 1987 Viking cabin cruiser. He hung up his captain’s hat in 1997, just a few years before I was born.
Unlike so many pilots, I don’t come from an aviation family. In fact, I don’t know of a single pilot in my family’s history. It took many years for me to accept that I often looked forward to family trips as a kid more for the airplane rides than for the destinations themselves. Today, being more honest with myself, I love the sound of the overhead bins clicking shut and the thrust of two jet engines pushing me into my seat.
When I expressed my desire to become a pilot, my family’s responses were mixed: my father was intrigued, but my chronically aerophobic mother immediately envisioned the worst. And although she denies ever saying it, I recall my grandma telling me that she would never let me fly a plane.
On the other hand, my grandpa’s eyes lit up. During my primary training, no one asked me about my flight lessons as often and as eagerly as he did. Over many dinners and phone conversations, we enjoyed comparing our two hobbies: navigating in his time with a compass, a chart, and a prayer, and in mine with a Garmin GNS 430W and my iPad. We shared stories—my grandpa’s of saving his boat from peril, and mine of practicing engine-out landings during my lessons. He may not be an aviator himself, but my grandpa and I share an adventurous spirit and a yearning to master our respective “blue yonders.”
Visiting Norwood Airport with my grandparents in the summer.
On warm summer days, my grandparents and I often brought lunch to Norwood Airport (KOWD) to watch the planes in the pattern. I taught them tidbits about aviation, and they asked me about my aspirations as a pilot. Together, we fantasized about the day when I would fly to Norwood myself, bring them through to the other side of the security fence, and introduce my grandpa to the sky.
I became a Private pilot on May 12, 2023, at my home airport in Beverly, Massachusetts (KBVY). With the ink on my temporary certificate still wet, I began preparing for my grandpa’s first flight. After years of high expectations from both him and me, I wanted to do it right. The big day finally came on a Sunday afternoon in June, and I was ready—since taking my checkride, I had rehearsed my planned flight with my CFI and by myself. It was a bit hazy due to the wildfires in Canada, but warm and sunny nonetheless.
I was filled with anticipation as I flew my favorite rented Piper Archer to Norwood. I landed smoothly on Runway 17 and taxied to the FBO, where my grandparents waited restlessly with my aunt, uncle, and cousins. I did my best to be a good ambassador to general aviation, answering lots of questions and taking pictures with each of my family members sitting in the right seat and smiling out the door. While my family listened, I carefully completed a passenger briefing with my grandpa.
My grandpa and me, about to take off on our first flight together.
Soon enough, my family returned to the FBO building, and my grandma wished my grandpa a safe and fun flight. The ramp agent helped him climb onto the wing and into the right seat, and for only a split second I wished that I had learned to fly in high-wing Cessnas instead. We adjusted my grandpa’s seat, and I introduced him to the instrument panel, yoke, and rudder pedals. With a “CLEAR PROP!” I started the engine and we taxied out to the runway.
After a successful run-up, my grandpa jokingly delivered the Yiddish phrase that my family often offers each other before we embark on commercial flights, “geh gezunt aun kimme gezunt” (go in good health and return in good health). We laughed together as I lined up on the runway centerline and received a takeoff clearance.
The Archer leapt off the ground just after the thousand-foot markers, and I noticed my grandpa struggling to hide a grin behind his video camera. My workload increased as I turned on course, scanned for traffic, and switched to the Boston Skyways frequency for a city tour clearance. Over in the right seat, my grandpa took the opportunity to sit back and enjoy the sights and sounds of the city from above.
Under the watchful eye of Boston’s tower controllers, we entered the Bravo airspace below 1,500 feet and observed the skyline getting closer. We took in the sights together, getting up close and personal with some of Boston’s most prominent and historic landmarks. After passing Fenway Park and the Prudential Building, I realized that my grandpa hardly needed me to give him a tour of the city he has lived in since before I was born. I stopped narrating and let him point out the Zakim Bridge and the new Encore casino, which sticks out against the relatively flat terrain in the area.
During our second loop around the city, I offered my grandpa the chance to fly. He replied enthusiastically, “Sure!” I demonstrated a positive transfer of the controls, which we had previously briefed, and the airplane was his. With my guidance on pitch and roll corrections, he maintained level flight. As we approached Logan Airport once again, I asked Skyways if we could fly southbound over Boston Harbor and was approved as requested. This provided us with incredible views of Logan and the airliners landing and departing.
A photo of Boston’s Logan airport that I took on this flight.
I took the controls back, thanked Skyways for the tour, and exited the Bravo to return to Norwood. My grandpa always seems to have just the right thing to say, so despite a bounced landing, he exclaimed, “Beautiful!” Taxiing back to the FBO took only a minute, and after the engine shut down, he smiled contentedly. “Zachary, that was amazing.” Just like that, my first flight with a passenger—and our first flight together—was over.
The sun started to lower in the sky on my flight back to Beverly, and I couldn’t help but reflect on the experience of taking my grandpa for his first flight in a small airplane. On that warm summer day, my relationship with my grandpa had changed in a way. Not only was I his second-youngest grandson, but I was now also his fellow captain, whom he had trusted so profoundly to introduce him to the wonderful world of general aviation.
While I look forward to enjoying many more flights with my grandpa in the years to come, I recognize that someday we won’t be able to fly together anymore. When that day comes, the memories of our flights together will become all the more precious to me.
I am so grateful to have photos and videos of me and my grandpa enjoying aviation together. I can’t wait to show them to my own children and grandchildren one day, encouraging them to relentlessly pursue their passions and connect deeply and genuinely with their family members. I will always cherish the memories I made with my grandfather that day, sharing the skies and the special type of magic that only a little old airplane can provide. I may not recall him asking to be my first passenger, but the truth is that no one could ever have deserved that seat more than my grandpa.
- Very Precious Cargo - February 27, 2026
Best first passenger you could ever have. Great article
Thank you, John! It was my privilege to take him flying.
What a wonderful experience as it triggered a tsunami of memories for me as I recalled taking my mother aloft just after earning my PP. She was a CFII, though not mine, as she did not “want to teach me her bad habits,” though in reality, she had none. Enjoy many more flights with your Opa, and “ Bleib gesund.”
That sounds like a wonderful experience, Dan. I’m glad you enjoyed the article! I hope to take my mother flying one day, but I’m not counting on it :)
Sounds like building an experimental is in your future! Enjoy your aviation journey. The fun has just begun!
Steve, I sure hope so! It’s definitely on my bucket list.
Oh boy, what a delicious memory for both of you. My father was the one who brought me to aviation and helped me accomplish my goals. On the other end of the spectrum, I flew for fun for around 60 years but my phobic wife only agreed to sit in the plane, on the ground only, once along the way. My assignment was to respect her personal instincts.
Sounds like you have some incredible stories from your flying career, David! I’ve been very happy to share a few flights with my father so far, and hopefully many more to come.
Zachary,
What a great experience, and you told it so well. I find it especially notable that you planned and flew a “vanilla” sight-seeing tour, without any high-risk flybys or other such temptations for a new pilot.
Well done!
Thanks so much, Andrew! I try to aware about good ADM. Of course, there are times when I realize later that I could have made better decisions, but hopefully that rate will decrease as I fill up the “experience” bucket. I’m glad you enjoyed the article!
Deeply moving story. Thank you for sharing.
Kol HaKavod
Todah rabah, Lee!
After reading this exceptional account, I am sure your grandpa must be enormously proud of you for your achievements and equally grateful for your extraordinary love. You’re a lucky guy to have him and he’s so lucky to have you. Hope you have many more flights together.
Thank you, Richard! I am indeed so lucky to have him and I’m always grateful for his encouragement of my flying!