While not exactly what you are planning, a good read is "River Horse", by
William Least Heat Moon. A few guys take a 26' power boat across the country
east to west. They start by going up the Hudson.

Obviously they have to portage from time to time, but it is an interesting
look at small town America.

Yours sounds like a fun trip. Probably easier in a power boat.

A guy from the local YC did something like this, but he left his mast at
home.

Good luck.

Bill ( RI also)

"Richard Malcolm" wrote in message
om...
My brother in law and I are thinking of taking his 41 ft
morgan next season from RI to NYC, up the Hudson, Erie canal? West to
Chicago and down the Mississippi and on to Florida where he
wants to sell the boat (and then think about buying another
boat) While we are very much in the planning stages, we were
wondering what ideas you may have about the trip and when
and where we would have to deal with the 2 mast. One is 55
ft long.
any help would be great! What time of the year would you
start? how long should we plan for? which route would you
take? etc we would be doing this in stages with others
taking on part of the trip as we could not get that much
free time.
thans