I have heard some scary stories of guys dodging barge trains on the
lower mississippi.
It might also be interesting to retrace Lewis and Clark with the
portage across the continental divide and other choke points done on a
trailer.
Maybe I am just thinking about it because that is all you see in that
whole midwest/west area when you are up there.
I think the US Park System will stop you at the Yellowstone park
wilderness area. I know there was a big controversy about whether they
should even allow kayaking in the park when I was there. (you can't
now).
Once you pulled out there you could start back up on the Snake but you
would need to "portage" over about 20 dams.
That is all just a dream tho. I haven't even been from here to Stewart
;-)
===
There's no reason why you couldn't go to Stuart and a lot farther in
your pontoon. With shallow draft you don't even need to cross the
open part of Lake Okeeechobee although you could on the right day. We
have seen a lot of pontoons going north on the ICW portion of the
Indian River and beyond. With some camper canvas and judicious
weather selection there's no reason why you couldn't make it to the
eastern end of Long Island Sound.
If you want some real inspiration about what can be done in a small
boat, take a look at this: