Ready to tack,” Chris said, nodding to our nephew Truman, who sat cross-legged in front of me, his eyes wide with anticipation.
At just 10 years old, Truman was now the same age Chris had been when he started racing in the High Sierra Regatta with his father. I was witnessing the proverbial tiller pass from one generation to the next as Truman scrambled into the cabin of our Victory 21, Geronimo. Moments later, with the maneuver complete, he popped back up like a seasoned crewman and found his place on the rail, just as Chris had instructed him. The transition was almost second nature.
“He’s good blood ballast,” I quipped, chuckling as our sensitive little boat responded favorably to the added 80 or so pounds. Every bit of weight and inch of adjustment makes a noticeable difference, as the elders of our fleet have been telling us for years.
This race was special for many reasons. Chris and I have been sailing together for 10 years, but this was our first regatta with a third crewmember. Let’s just say that in years past, the way we conducted ourselves was not exactly conducive to having little ears aboard. This year, though, something had changed. Maybe we were still riding the high of our second-place finish aboard Avocet in the Banderas Bay Regatta in Mexico, or maybe we were ready for a new chapter. Either way, we were thrilled to have Tru on the water with us—and after two solid fourth-place finishes, we were certain it wouldn’t be our last regatta as a crew.
After our final race (which ended in a photo finish), Chris handed over skipper responsibilities to Truman, who navigated us back to the marina. Watching him, you could see the subtle shifts in his focus—the way his small hands guided the tiller with growing confidence, his eyes locked on the telltales as he read the wind’s subtle shifts. His voice, though young, rang out with the command we’d taught him—“ready about”—both timid and confident in equal measure.
Chris and I were in awe of his raw talent, but there was no real surprise that he was a natural. After all, he has Neely blood in him. It’s about 80 percent salt water and 20 percent wanderlust. Chris spent his formative years sailing with his family on Sea Castle, a Mason 43, navigating San Francisco Bay. His older brother Jon later bought his own bluewater cruiser, the Hans Christian 33 Prism. Sailing was more than a pastime—it was a family tradition, a bond forged through wind and waves.
Back in 2021, when Chris and I cast off for cruising adventures on Avocet, our Cheoy Lee 41, we promised ourselves that summers would always be spent back home, anchored in family. Part of that promise meant making lasting memories with our nephews before they grew up. During those sun-soaked summers, we noticed Truman’s natural affinity for sailing. His comfort with the elements came so easily that Chris and I offered to foster that talent.
After securing approval from Truman’s parents, we set out to find a boat that he and his brothers could call their own. Something small but capable where the boys could learn and grow as sailors. Our search led us to an International 14—a classic choice.
I’ll never forget the sheer excitement in Truman’s eyes on Christmas morning when we unveiled it. The boys christened it with a splash of soda on the bow and the name Bluey on the stern. Since then, the whole family has enjoyed countless sails on California’s Huntington Lake. Truman’s love for sailing has only grown, fueled in part by his time at Gold Arrow Camp, which holds its own legacy of sailing on those same waters.
I often look at old photos of Chris at that same camp, stretched out on a Sunfish with the unmistakable Neely grin and zest for spending time on the water. I see the same sparkle in Truman’s eyes.
“And in fifth place, the crew of Geronimo!”
The sound of applause brought me back to the present. Chris was off helping friends load their boat onto a trailer, so Truman and I made our way to the front of the crowd. The trophy wasn’t for first place, but the sense of accomplishment glimmered all the same.
I held the microphone and thanked the fleet for nurturing our love of sailing as well as the budding passion of our new crew. I said that I hoped to see Truman on the water again next year, continuing the family tradition.
This regatta marked the beginning of something new. Our journey now had a third crewmember to share in the adventure—someone to help carry the legacy forward.
Who knows? Maybe someday Truman will help our future kids, his cousins, learn to sail, passing on the same knowledge and love for the water that we’ve shared with him. Sometimes, you just have to pass the tiller.
