Re: Norfolk, VA to Boston delivery
If you're buying the boat in Annapolis and taking it to Norfolk for some work, then from Norfolk to Boston. I don't know if I'd go back up the bay to the Delaware after heading down.
As Rich says this is a trip at that time of year that will be dictated largely by the weather
(aren't they all? ) So as jsaronson says, I'd consider my option to look at going offshore to Block island..or making a jump to Cape May then on to block. Then up toward the cc canal.
Another alternative is to head to the Highlands from Cape May and then make a decision from there whether or not you want to stay inside or go outside to block.
There's a dozen ways to do this trip...level of experience, weather, crew, soundness of vessel are all going to be deciding factors. If you go outside from norfolk, you'll be out of VHF range at points for anything but nearby traffic, certainly out of cell phone range, so long range communication would be prudent if not essential. as would life raft, epirb etc.
Were you planning on having someone who has offshore experience onboard? The overnight from Norfolk to Cape May might be a good test of your offshore tolerance. ( weather permitting)