I've been searching around Vimeo for sailing documentaries and stumbled across a few good ones I'd like to share. These offer a great glimpse on what it is like to cross oceans on a small sailboat, all of the good and bad things.
These are segments from what will be a full length documentary about a guy near my age who buys a small boat (26 foot Contessa) and sails from Holland all the way back to his home in Australia. While my inspiration to fix up and sail a boat is a bit different than his, I can relate a lot to him.
Trailer for the full length: