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?