I take it all back...this guy is a rockstar...
On this topic of sailing upwind and tacking, even with our crappy, bagged-out, unshapable sails on that C27, we got pretty good at sailing upwind (note the windex)...
Is this just pinching? Well it can be a fine line. One of our proudest accomplishments on that lake was beating a Beneteau 345 upwind (friendly race) back to the marina. Talking at the dock he was blown away that a C27 could sail that tight and fast - especially with crappy sails. I assured him it wasn't the equipment. Heh-heh.
Even though the usual group above are trying to paint my comment as another "attack" of some sort (a seriously tiresome game) - my point remains that most leisure sailors cannot sail upwind or tack very well - certainly not compared to racing sailors (the example in that 120° story I mentioned). That's just the truth. Over the years of racing we got pretty good at it - but I still don't consider myself great...despite the pickle dishes. It's a serious art...and those pickle dishes were mostly offshore regattas with a lot of cruising boats...not hardcore racers.
Try roll tacking a 420. Oh, sorry, that's for the cannabis thread.
I have no doubt I'm going to have a huge learning curve for getting good upwind performance and solid tacks out of our cruising multi when the time comes. But I also have no doubt that with practice I'll get pretty good at it (if I care enough to try that hard) - and will very likely be able to out-sail many, if not most cruising monos upwind. Our little beach cat is teaching us a lot in that regard. Kinda like that 420.
I already know for sure I couldn't beat FIASCO! back to the marina in our B345-crushing-C27 on this same lake. And that's saying something.
In the mean time, I encourage everyone that was offended above to post photos or videos of their upwind sailing and tacking to show me how it's done. I'm always eager to learn.