O C Diver: The plan right now is leaving around Labor Day and getting to the Bahamas around January / February. We are trying not to get locked into a rigid schedule, just staying ahead of the cold.
Ok, I would start first with planning hurricane safe locations. I'm not dissuading you from leaving then, but you might pick destinations from September through atleast the end of October for safe harbor. This doesn't obligate you to visit them, but maybe be within a week of one forward or backward.
Places I would consider North of Savannah would be:
Block Island maybe for a few days.
I'm not a fan of cities, but:
New York city has lots to offer although expensive. Anchor a night behind the Statue of Liberty, breath taking view of the city. Visit the The Intrepid Sea, Air and Space museum.
Baltimore's Inner Harbor is nice, but get more current information about safety in the city closer to your departure.
Chestertown is a nice stop for the weekend.
Annapolis is a decent stop for a day or 2 in the fall. Depending on your preference, you may want to plan on, or plan to avoid the 2 weeks of boat shows.
I like anchoring out and dinghying in to Oxford and St Michaels.
I haven't been to Solomons by water, but an interesting stop.
I would plan on spending some time in Norfolk. Put the Battleship Wisconsin on your visit list.
You will have a choice between the Dismal Swamp canal and the Albemarle and Chesapeake canal. They are very different. I enjoy the wildlife and the history of the Dismal Swamp canal but the other offers mediocre prime rib.
I would recommend doing the Dismal Swamp atleast once.
There are some nice towns along the Outer Banks of NC from Nags Head down to Ocracoke. I don't tend to visit them as I spent a lot of time in Frisco, Hatteras, and Ocracoke while working. Ocracoke is often mentioned as a stop when heading South.
If following the traditional AICW, Elizabeth city, Belhaven, and Oriental are all good overnight or lay day stops. If you like to anchor out, Greens Creek behind Oriental is very nice, but you must dinghy in to M & M's for dinner (state law
).
I'm going to let you digest those for a while and will add some more later.
Ted