Most of this has been on the Watertribe Forum before but I like it enough to highlight it again. Please comment with other great adventure sailing videos if you know of any.
Laser2 sailing 2000km,36 days Slovenia-Albania-Slovenia from igor Stropnik on Vimeo.
Project Scandinavia 2012-Sailing from Nordkapp to Stockholm by Igor Stropnik from igor Stropnik on Vimeo.
Hold Fast from Moxie Marlinspike on Vimeo.