Sorry I realize I'm necroing this thread, but I bookmarked this long ago and finally got around to watching it. There has been some other sailing posts recently, so this might be of interest to some new people.
I sort of enjoyed this documentary. It had some interesting tidbits on sailing. It's sort of the dream isn't it? Just to drop everything and go adventure.
That said I got pretty sick of the guy. I didn't really mind him being anti capitalist or anti consumerist, but I did get annoyed by his attitude about it. I think those notions genuinely upset him. It got tiring listening to him talk about it.
I also found him to be pretty pretentious. This is especially displayed in the scene where he has trouble making his way through a narrow channel due to the winds and the cruise ship. He got mad about it or as he put the situation, it was "insulting" that the people on the cruise ship were having a party. I can understand the frustration, but everyone has a right to do what makes them happy. The people on the cruise ship are just out having a good time. I can't be sure, but I think he also had a working motor at this point, so he could have just motored through rather than bitch about it.
If you can get over those points, I think this documentary is worthwhile. It has some good shots of sailing. It shows the struggles of sailing an old boat and the work required to keep it sea worthy. Not a terrible way to spend an hour.