I rarely turn down an invitation to race a boat that’s new to me. So when my friend Steve Orsini extended an offer to come race a Lido 14 with him at the W.D. Schock Memorial Regatta in Newport Harbor, Calif., in March, I instantly added a few more days to a planned trip to the Oracle RC44 Cup San Diego. I had no idea what to expect of the Lido 14, and knew nothing of it, really, except that it’s not seen much outside the Golden State. I was eager to jump into something different, naively assuming my dinghy skills would allow me to master it after a few practices. It’s a two-person dinghy with main and jib, a whisker pole, and a few basic sail controls; what could be so tough?

Steve is an excellent sailor and has raced Lido 14s for many years, so he knows what makes this quirky little boat do its thing. Yet barely 10 minutes into our first practice session, I start suggesting a few adaptations to his otherwise proven techniques: what if we roll a lot harder in the tacks and jibes? Instead of sitting on the windward side to get the boom up downwind, why don’t I stand up so I can better see the puffs? How about a little less jib halyard tension? On and on it went, all in an attempt to get something more from a boat already sorted by generations of the West Coast’s best and brightest sailors.

Steve chartered the boat from John Papadopoulos, whom I understand has written the book on Lido 14 sailing. He’s one of those fanatical types that embraces the art and science of tweaking the untweakable. He even builds his own class-legal carbon-fiber rudders.

The evening before the regatta, after our brief practice, we dined with John, and I peppered him with questions. He was forthcoming with tips on rig tension, weight placement, and whisker-pole management. He had answers, and then some, and maybe sensed where I was coming from with my line of questioning.

“Many a hot-shot college sailor has tried to come out and change the way we sail them,” he told me, “only to be disappointed.”

Human nature being what it is, come race time, I applied some of my own variations on a few things. My apologies to Steve, who patiently put up with it every step of the way, especially my overly aggressive roll jibes. On more than one occasion, a gallon of water would pour into the boat as the rail submerged under my weight.

“Whoa! Easy on the roll there, Dave,” he’d say, as I’d reach for the bailer and sponge.

During our practice session, we’d debated about whether to switch the whisker pole before or after the jibe. His normal crew prefers to do so before, but I was convinced it was better to let the mainsail come across and power up before jibing the pole. After we bumbled our way through a dozen or so jibes, we finally agreed it felt better to jibe the main first; we then had to fine-tune Steve’s choreography with the jib sheets. After all that, we nailed a few jibes, and they sure felt better.

As for my technique of standing up on the centerboard trunk while sailing downwind, it seemed right to me initially, because I could adjust my weight more effectively, but I stuck out like a sore thumb. Every other crew was tucked in the forward weather corner of the cockpit, weight concentrated with the skipper. A few would sail right past us, probably wondering, “Why’s that guy standing? That’s not how it’s done.” In hindsight, I should’ve taken a seat. I suppose that’s why the seating is there in the first place.