Congratulations. Ones first cruise is always a special memory.
Since we have cruised those waters many times, we can probably help with most of your questions.
First question, there is an excellent shelteed anchorage on the Trent River in New Bern, NC. It is only a 17 mile sail from Oriental o the Neuse River to get there. Best of all, the anchorage is. Only 1 mile away from the New Bern regional airport.
Sailing is difficult on many parts of the ICW,, but the open waters of The Chesapeake and in NC are the best.
Be sure to choose The Dismal Swamp Canal route. It iwas s magical.
Post new questions here if you want. Many other WOA members know those waters too.
or email dickandlibbymills@gmail.com
You should also check out my blog, dickandlibby.blogspot.com. There are 2700 posts there about cruising the East Coast. Especially relevant would be posts from 2005: Our first year cruising. I bet that there is a post on thst blog for every possible route and most possible stops and good anchorages between MD and Charleston.
Fair winds and following seas.