Sailingdog, muchos gracias ... I guess the first step would be to download the free NOAA charts so I have a clue where all these places are that you mention
For me, the journey is the destination. Besides escaping the northern winter, I would also want to visit and explore places I've never been to (which is really any place south of DC and north of Miami). No hurries here, there's really nothing waiting for me in Florida.
While cruising, I'm cheap and generally prefer anchoring to mooring to slips, but this may be different as I would live on the boat through the winter. Once in Florida, I would most likely be looking for a comfy marina where one doesn't absolutely need a car too get around.