I pull up a plastic cafeteria-style chair and sit alongside my 92-year-old grandmother, she in an adjustable recliner, smothered in sheets to ward off the frigid air in the hospital’s intensive care unit. Attempting to steer the conversation away from what is ailing her, I take our conversation elsewhere by turning to the topic of sailing. “Did you watch all the boats starting their race to Bermuda?”From her front lawn, she says, she did in fact watch the fleet leave. Once I get her talking about it, she eventually wanders off to a story about how my grandfather, a career navy man, but not necessarily a wind-driven sailor, once capsized the family Comet, briefly leaving her adrift in Narragansett Bay. This particular Comet, I then learn, actually belonged to my father. As a young Newport wharf rat sometime in the 1950s, she says, he got it into his head that he had to own one of these 16-foot doublehanded dinghies, which were popular at the time. He pleaded with his parents for a little financial assistance, only to be turned down, but his older brother, she says, who had no real passion for sailing, ultimately gave him the money to buy it.”All summer long he’d sail that boat all the way up the bay to bring it to the different junior regattas, and we’d drive there and pick him up,” she tells me. “I think he often slept in that boat, too.”It’s the only thing he really had, and he was always in it. He’d be gone all day, and after dark, we’d start worrying and go down to the club, but then, there he’d come, around the corner of the harbor, not a care in the world.”I realize there’s nothing unique about my father’s childhood exploits in his Comet (hull No. 5), but hearing this story for the first time excited me because it revealed a deeper connection with him, one I never knew I had.I remember as a kid, at a similar age as he was when he had his Comet, of wanting nothing more than to be on the water. After my sailing lessons, and even days when I had none, I’d pester the sailing instructors until they let me take one of the tank-like Turnabouts on my own, outside of our allotted class time, and well outside the harbor confines when they weren’t paying attention. Later, it was in the Club 420s; if my crew and I wanted to race in one of the weekly junior regattas elsewhere on the bay, we had to get the boat there ourselves, on its own bottom. Off we’d go, spinnaker reaching up the vast open bay-no charts, no concern for the weather; nothing, except a ride home at the other end.In hindsight, and especially by today’s unfortunate standards, maybe it was a little irresponsible on my parent’s part to let me freewheel around the bay unsupervised, but it was the best and most important sailing of my life. I realize times have changed, but somehow we must occasionally break away from overly regimented sailing programs and leave the coach boats onshore. Instead of watching over our young sailors’ every tack and jibe with a critical eye, we need to give them the opportunity to put up a sail at will, have an adventure, and build the self-confidence that will remain with them for a lifetime.And this is what excited me about my grandmother’s story that day. I’d never realized that it was my father, who, through his own experiences and escapades, had indirectly cultivated my infatuation with the sport, not by pushing me, but by simply allowing me the freedom to find out for myself. It made me wonder where I’d be if it weren’t for my old man and his Comet.