I don't have any knowledge above Paducah at the mouth of the Tennessee River, but have made the trip from Kentucky to Punta Gorda. If your mast (including antennas, etc) is less than 52 feet and you adjust for rises in the normal pool, you can go from Paducah to Mobile with the mast up. I went in a Cabo Rico
38 and we cleared all the bridges but some were close to the antennas, but we never did scrape.
Look at Active Captain
and the electronic waterway guide and you can get a lot of information on marinas
etc. Also check the notices about lock closures - listed in the Waterway Guide. Below Demopolis there is only one place for fuel and that is Bobby's Fish
Camp just above Coffeeville lock. That is around mile 118. From there to Mobile, You will have to anchor
out and make it on the gas or diesel
you can carry. The River is narrow and the anchorages on that stretch are few and far between, so ample planning is required.
Once in Mobile, you can get to Pensacola
with the mast up. The controlling bridges east on the GICW are 49 feet past Pensacola
. if you are higher than that, you will have to go outside to Panama
City or Port St. joe. There is a 49 foot bridge on the GICW between Panama
City and Port St. Joe, after that to Appalacacola on the GICW you can get there if below 65 feet.
You can also go offshore
at Pensacola to Clearwater. That is what a lot of sailers do. You wait for a "norther" and run from there.
Hope this helps with your initial research