First, I'd aim for doing 40-50 NM per day at a minimum... otherwise, you'll looking at an awfully long trip. Avoiding the ICW would be a good idea, since much of that is not really good sailing due to channel restrictions, etc.
I'd also recommend hopping offshore to go from NYC to Cape May, since there really isn't a good ICW route there. Be aware that most of the harbors on the New Jersey coast are horrible and not advisable as ports of refuge in bad weather, so plan your trip accordingly.
I prefer going offshore from Cape May to Norfolk, but singlehanding, that is a bit more difficult. However, it does cut a good distance off your passage. It also avoids the C&D Canal and the Chesapeake.
Going inside the ICW at Norfolk, which is where it really starts, and taking it down to past Cape Hatteras has basically two routes—the Chesapeake-Albermarle canal route, normally called the Virginia Cut route; or the Great Dismal Swamp route. Both are pretty much mostly motoring, and the beginning portion is the same for them both.
Some good marinas along the Virginia Cut route are:
- Tidewater Yacht Agency Marina
- Atlantic Yacht Basin, which is an excellent jumping off point for making the series of bridges and single lock at the northern end of the ICW route heading south.
- Coinjock Marina
- Alligator River Marina (not one of the better ones IMHO, but the pickings are slim in this particular area) :p
- River Forest Manor Marina—While I didn't stay at this one, I did work on one of the boats I was delivering there, and the people there were aces.
From Belhaven, where the River Forest Marina is, it is a fairly short run, about 45 nm, to Oriental, and only about 25 nm more to Beaufort.
Going out at Beaufort and hopping down to Cape Fear isn't a bad run, but it is about 90 nm. The Bald Head island Marina is a great place to stop, but the facilities there are a bit lacking... only a single shower/restroom for a fairly large marina. Eb and Flo's has great food and pretty waitresses. ;)
Hopping from Cape Fear to Charleston is about 130 nm. Winyah Bay is a possible stop between the two, but I've not been there, so can't say much about it. It's been a few years since I stopped in Charleston, so can't really say what's good there anymore. :D Ditto for St. Mary's.
Charleston to St. Mary's/Fernandina Beach is about 165 nm or so outside... and I'd do that to avoid the Georgia section of the ICW. The ICW in Georgia is really pretty in place, bug-ridden in much of it, and not very straight, being made of a lot of oxbows and such. It also has been neglected and not really maintained all that well for the past ten years, though that has started to improve.
St. Mary's to St. Augustine is a nice short 55 nm hop outside, a bit longer, inside the ICW. Definitely stop at the St. Augustine Municipal Marina, which is one of the best marinas I've been to, especially considering it is a municipal marina. Even if you're anchored out, you can pay a dinghy dock fee and get use of the facilities there, which include laundry, showers, a lounge and bathrooms.
As for books and such...
You'll probably want Cruising guides for the east coast... Maptech's embassy guides
are a good start.
You'll definitely want Skipper Bob's
ICW guides, although I try to avoid the ICW like the plague that it is.
You'll want charts, chart kits or waterproof chartbooks of the entire east coast. I prefer the Maptech type waterproof chartbooks, but the chartkits definitely have more detail.
As for Florida—are you planning on anchoring out most of the time, using a mooring or staying in a marina? That will make a big difference.