I enjoyed watching a documentary ( "Maidentrip" http://www.imdb.com/title/tt2555268 ) about a young girl that sailed around the world just for fun. She did it in an older boat with limited electronics on board and had fun and made frequent stops just to visit other cultures.
Contrasted with another young girl ( "Wildeyes" http://www.imdb.com/title/tt1939787/ ) that did it for a record's sake, on a modern boat, with multiple sponsors, packed with electronics (all of which failed) and ultimately capsized in the Indian ocean.
And another good one was "Deep Water" ( http://www.imdb.com/title/tt0460766/ ) where a man tried to win an "around the world" yacht race (for a business venture) but ultimately went insane and jumped overboard.