I just was looking at Marinas in Jacksonville when I saw your post to my question. I guess my only concern with the area is that it gets a little cool. Averages in the 60s. Your post got me thinking though that we could start off in Jacksonville and then take the boat down the coast to Palm Beach or Ft.Lauderdale over the winter by doing long weekend trips.
Have you spent time in Jacksonville? Can you sail in the Intracoastal, is it wide enough and deep enough? We have a 5'3" draft on our boat.