I've never seen the Mississipi (my loss I know) but I did read Jonathan Raban's "Old Glory" which tells the tale of his journey from way up in the headwaters down to the delta in an aluminium runabout.
Not that I had contemplated the thought but it sure as hell knocked any idea of doing such a trip by sailing boat right out my head.
Jonathan Raban
Worth a read btw....as is almost anything by Raban. Well I think so anyway...