Sailboats are few and far between on the rivers. I was in OH and tried looking for boats anywhere that connected to the ocean. Every once in a while I would find something on craigslist, but it was really very rare. So when you find them close by, don't waste any time checking them out. Something like that Hunter
25 would be perfect for 1 or 2 people to cruise
down to the gulf...
The trip down to the Gulf is pretty well documented from the Mississippi
south, do google
searches for "great loop" cruising guides
. You'd have to look into the bridge heights on the Tenn. and OH... You can get inland waterway charts
from the Army Corps of Engineers. Any sail boat can have it's mast
unstepped for the trip down. And all of those rivers are deep enough...You won't be doing any sailing anyway, so make sure whatever you get has a good running motor
... and don't go in the spring when the rivers are up
Check Kentucky Lake and the Land Between the Lakes area's... There was a nice Gulf 29 for sale
on the OH river in Cincinnati recently...
If you really want to make the inland cruise
, Your most likely options will be to find a boat on the great lakes
and cruise south from there, or start in the gulf and doing the great loop back home.