Your current boat seems a bit short and small for the purpose of such a long trip. Pick something longer for speed, but still with enough capacity to camp out of.
You didn't say whether you were planning on taking the intra coastal waterway all the way down or paddling out in the ocean. Makes a BIG difference.
Break your trip down into sections of 7 to 10 days. Then just plan a series of those trips to make up the entire trip. Staying in a motel every week or so for a night will make the completion of the trip much more likely.
Be sure you like these three others.
Be sure you won't mind too much if you don't like these three others at the end of the trip.
You trip will be about 600 to 900 miles long. How many weeks do you plan to take? Are you planning on using a sail? Prevailing winds are from the southeast in summer. You might think about starting in GA and finishing in the Chesapeake, sailing or not.