I usually prefer sailing to weather if the going is not too rough, or too slow. Usually, I'll accept too slow (<4kts boat speed) until it starts to impact my desired latest time of arrival. I've motored into dead calm and I've motored into the teeth of 25kts. Neither is a lot of fun, but I'll take the calm every time. lol
Two of my most memorable sails were a 36 hour beat from Annapolis to Hampton on a friends Tartan 40 and a 9-10 hour beat from York to Deltaville on my boat. The Annapolis-Hampton trip was close hauled almost the entire duration and obviously required quite a few tacks. The York-D'ville trip required a few tacks out of the York River to mid bay where we tacked over to starboard and were done for the day as the wind clocked perfectly with our desired course changes so we stayed on starboard near close hauled and making >6 knots all day.
I'm really just now learning how to get my boat to go downwind with acceptable speed. Its a wing keel and downwind seems to be the slowest point of sail, at least until you start poling out the genoa or setting the asym.
s/v Palmetto Moon
1991 Catalina 36