Re: Trip planning
Looks like 65 miles from Annapolis to the east entrance to the C&D. If everything goes perfect you can probably do it in a very long day. I think I'd be shooting for Chesapeake City (52mi from Annapolis so, still a long day but ends in an easy anchorage with a place to grab some grub and a beer and coffee in the morning).
Come not here if you have already spent the best of yourself