Heading South on the ICW
Don''t know the level of your boating experience and especially your awareness in dealing with coastal winter weather, which can sometimes be SEVERE AND CHALLENGING at the time of year you propose. And, will your boat be ready?
The "Waterway Guide", Northern, Mid-Atlantic and Southern editions, are always useful; a tide book is essential; charts, of course; and some publication that shows anchorages and where you can buy the most essential services along the way.....though there is a good chance that you will simply go from marina to marina, plugging in each night to electricity, primarily for heat.
Right now, the weather is challenging, but not impossible. Occasional layovers, sometimes several days at a time, to let winds subside or temps rise a bit, but always ready to go......depending on the people, this can shorten or completely stop a trip from ever happening.....good luck.......