The Waterway Guide books have just about everything you need to know. http://www.waterwayguide.com/
I've done this trip over 35 times. The best way to go is sail down the west coast of Florida, cut inside of the keys and up into Biscayne Bay. (Miami) Then head offshore and catch the Stream all the way up to Beaufort, NC. If weather blows up beforehand you can always enter the ICW and head up the ditch, it just takes much much longer because you have to stop for bridges, deal with idiot traffic, and stop at night most of the time because you will just run aground in the dark. Plus, the canals, especially the Low Country in Georgia, are very meandering and cover WAY more mileage. Beaufort is a great town and very boat friendly with a great marina, and wild horses running around on the islands right off of the marina. Charleston is also a great place to stop in at about halfway, or enter the ICW.
At Beaufort you enter the ICW so that you pass inside of Cape Hatteras. It is not called the graveyard of ships for no reason. If your mast is over 65 feet you will have to go outside the whole way. It is ALWAYS blowing at least a gale off of Hatteras, but on the inside you can run up Pamlico Sound sailing at a great pace in protected waters as it is blowing like snot outside.
Stop in the River Forest Manor before you enter the Alligator-Pungo canal, they have a great smorgasbord. Don't miss it.
Coinjock is another cool place to stop. Depends on your boatspeed.
When you reach Virginia you can stay in the main channel or choose to enter the Dismal Swamp Canal, which is really awesome but they have not been dredging it for years and last I heard was down to five foot controlling depth, but it is worth the detour if you have a shoal draft. These canals were surveyed by George Washington.
This will bring you to Norfolk VA. Nice marinas here and of course huge Navy base.
After Norfolk you can either run back outside the rest of the way, catching the Stream again. Depends on your rush, the quickest is to get in the Stream in Miami and ride it the entire way, made Miami to Boston in six days in a forty footer. However you will see NONE of the sights on the way. On the other hand, made Norfolk to Ft Lauderdale in over a MONTH on the ICW the whole way in a 37 footer.
If its still blowing outside, head up the Chesapeake, thru the Chesapeake Delaware canal, and down Delaware Bay to Cape May, NJ. The Jersey shore MUST be run outside. There is an inside waterway but it has lots of shoals and low bridges and is only for small boats. Wait for good weather at Cape May to run up to NYC, or break outwards towards Nantucket if you want to skip Long Island Sound and Buzzard's Bay. I would recommend entering NY harbor, its beautiful, and a cool ride up the East River, through Hell's Gate and the Throg's Neck and into LI Sound. Nice run up the Sound, and then you can head out towards Block Island, Martha's Vineyard and Nantucket and round Cape Cod, or up Buzzard's Bay and through the Cape Cod Canal cuts off a couple hundred miles. This brings you to Boston and then you are almost at the border of Maine, which gives you another thousand miles of coastline.
Anyway, buy the Waterway Guides, they are great to read for planning as well as using them underway. Also get a copy of Eldridge Tide and Pilot book, has tides and currents for the whole East Coast and tons of other great info.
Also the Coast Pilot is a useful book to have:
It's a fantastic trip and there are lots of boats doing it all the time. Usually running SOUTH at this time of year and up North in the spring.