Slightly off topic but since your plans seem to involve flying to where your boat may be moored then traveling on the boat it might be appropriate, given the recent air travel situations. Dr. Walter Bradford Cannon of the Harvard Medical School (physiology Dept) investigated what some called acute stress response and he renamed it and it became known in the 1930's as the "Fight or Flight" response. Dr. Cannon had today's air travel situation pegged long ago.
Don't miss the TX and LA coastal areas. Good food, good people, plenty to do and see.
Wifey B: Also include thoughts of ease of flying in and out in your plans. We fly to and from our boats a lot. Flying from South Florida to Grand Cayman or to Panama City, Panama is easy. Flying to Seattle takes forever but fairly simple. Flying to Ketchikan, Alaska isn't fun or easy. Neither is flying to Lake Pickwick, TN. Oh, I'll tell you about that one in a minute.
Flying to NYC so easy.
So, like if you're on the FL coast and you're going to Apalachicola and Carabelle and then across to Tampa, St. Pete area. Look at flights. You're likely to find a heck of a lot easier in and out of Tampa even though further from your home.
Now, about Lake Pickwick.
-We can drive it in 13 hours. Could get up and leave at 7:00 AM and be there at 8:00 PM
or
-Charter a plane at $20k plus and do it in 4 hours.
or
-Fly commercial to Memphis. Sounds simple. Not. No direct flights so either connecting in Atlanta or in Dallas. 5 hours. And then, rent a car and drive an hour and a half. Then have to turn it in somewhere. Oh, and don't forget being at the airport either 7 days early or 1 or 2 hours depending on current mood. So, leave for airport at 9:00 AM. Fly from 10:30 to 3:30. Rental car at 4:00. Drive till 5:30. Then to location by 6:00. Arrive 2 hours earlier than driving. From leaving home till settled in 9 hours.
-Fly to Muscle Shoals, AL. Two connections. 9 hours, then a 1 hour drive so total about 13 hours.
The proverbial, "You can't get there from here." Chattanooga or Nashville would be easy. Not Pickwick.
Just keep it in mind.