This one starts off a little slow and disjointed, but eventually follows a couple crossing the Atlantic from the Canary Islands to the Caribbean.
Blue Water (part one) from Richard Gooderick on Vimeo.
Blue Water (part two) from Richard Gooderick on Vimeo.
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:
Getting your Bearings / Sea Fever from nickj on Vimeo.
Lisbon to the Canary Islands from nickj on Vimeo.