[Spuds]

Originally Posted by MuseChaser

That all makes sense. I should probably spend more time sailing with just the headsail or just the mainsail to see how the boat handles. When both sails are up, I try to balance the trim so there's a bit of weather helm for safety, i.e., the boat gradually heads up when I take my hands off the tiller. Under mainsail alone, there should be even more weather helm naturally built in, so cleating off the mainsheet as you suggest would make sense, although when hoisting either sail I've always left the sheets free. If I head directly upwind (I do have an 8hp outboard), cleat the mainsheet so the boom is centered, then hoist the main, will that keep the boat pointed directly upwind without lashing the tiller?

I should probably just "sack up" and go out and try a few things... but it's kind of like flying.... most of the time, it's boring, but when it isn't, it's absolutely terrifying.

Hmmm... Maybe. I guess the problem is you would start traveling backwards which would push the tiller one way or the other unless you held it in place, thus the boat would start to spin. Which actually sounds like a great way of getting back on course without an engine now that I think about it. Idk. Try it with someone else for safety next time you get a chance?