Several years ago a fellow did it and brought along students from different film schools to document. It was shown on PBS in a seriers (I believe) called On The Waterways. Been my dream ever since. That and Alaska's inside passage by trawler.
Like the ICW these are trips I think every boater would love to make once. But like most trips get old by the 2nd or 3rd time. Guess that's just our wonderlust.
ANYBODY NEED A CAPTAIN FOR THE LOOP give me a shout (Maybe even done in pieces).
The Alaska trip...I'm thinking (dreaming) of 6 months in an RV across to Vancover then trading that for a trawler and 6 months on the passage. Then I can die broke but happy.