sailing South on the ICW

[mdsdurango]

I retire the end of this year and have been scouring the internet for information about sailing (motoring) the Intracoastal waterway heading south from somewhere in the north east. My thought is to purchase a 30 - 36' boat in or north of Virginia and head south. FYI - I am a decent inland sailor, not highly experienced with big water other than three ten day charters in the Caribbean. I am thinking that this could be a good way to get in some cruising experience without too much risk. I am looking for a learning experience along with the adventure. Boats are plentiful but info about traveling the ICW south is not.
I have a lot of questions but maybe most of my questions could be answered in a discussion. My first question is where is the best place to start? I have looked at boats as high north as Massachusetts but find very little info on the ICW from there to Boston. I would very much appreciate any guidance, links to information, forums, books, etc. Anything that can help me make informative decisions. I am currently reading The Looper's Companion Guide. I'm not that interested in making the inland loop. I want to learn the ropes of cruising starting in a reasonably safe environment. I would be single handling.
I am all ears and will take all advice with seriousness.
Thanks in advance.