My old boat, 50 year old design, a centerboard yawl, doesn't point very high. I knew that from reading long ago. And I have a friend with a J35. If we're sailing to windward together, he points higher
A couple years back with my college aged son and daughter as crew, we took our boat across the Gulf of Maine overnight(something we've done several times). This time, instead of just powering into the southerly breeze, I offered," Instead of motoring for 24 hours, what do you say we allow ourselves 36 or so, and just sail?" "Sure", all around. They love to sail rather than motor anytime.
Our forecast was south winds, our course,...south. To make a long story short(I appologize to anyone who's heard the long story), we made 3 tacks. Starboard, port, starboard. At times, we seemed so wide of a logical course, I didn't figure we'd finish under sail.
We used our WP for all the steering. Conditions ranged from 5kts on the nose, building to near 20 on the nose for the final tack, and a lot of water on the decks(we stayed dry and warm below or behind the dodger and spent little time behind the wheel).
We never attempted to point as high as the boat would allow, instead falling off to keep the boat on her feet, make it easy for the WP to steer(it did the whole way), and make it easy on us as far as how the boat handled the waves(my daughter, like her mom is prone to seasickness unless you make the boat sail, so they don't get sick;it can be done usually).
Leaving from Tenants Harbor area, we arrived at the Cape Cod Canal about 32 hours later. If I recall correctly, we covered about 180 nm on those 3 tacks. That was our fastest crossing, and most have been made under power on the shorter rhumb line.
I remember our tacking angle on the chartplotter, it was pretty pathetic.
It was an amazing trip though, and our old boat goes to weather. I took this shot on the port tack into the setting sun that night