I'd love to charter with just us two, but we bring friends to help cover costs. I'd never again go without AC in the summer (we had a rainy week with closed hatches and a boat full of mosquitoes, covered in DEET head to toe) - NOT sexy.
We sail on the lake at home alone all the time, but I haven't spent enough time driving to feel comfortable doing it on a chartered boat. My husband must be pretty good at it though, cause I don't think I've ever missed a mooring ball. Good advice about having just one at the bow, as I recall the only time we struggled was when a friend tried to "help" me.
We've also never had much wind, so lots of days were motoring anyway. You could always just do that, and enjoy the peaceful boat to yourselves. <img src="http://www.traveltalkonline.com/forums/images/graemlins/Wink.gif" alt="" />