OP here with a follow-up...
Thanks for all the recommendations. The trip at the end of October was not as long as initially thought. I did rent a Road Glide for 4 days and made the most of it putting on almost 1,000 miles.
One day consisted of a tour through the rural ranch and farming areas of the NW panhandle of Florida into Alabama with a group of about 25 bikes. Amazingly beautiful areas that I would not think of when I think of "Florida."
Another day I went to the USS Alabama. Great museum for history buffs! My only regret about that visit was not allowing enough time to really take it all in. Next time I visit I will allow at least 6 hours there... only "skimmed" it in 2 hours which was a decent overview, but not enough to delve into the details.
Other days were tooling around with family who also ride, riding along close to the shores of the two states... and eating dome decent seafood. This was the first time visiting the Pepsicola area and look forward to returning again sometime.