Not sure what your preferences are: marina vs anchoring
out etc. Also not sure how much time you want to spend in the Baltimore/Annapolis area. If you provide more info about your preferences, I might have more advice. Being a cheapskate most of my experience is anchoring
out or finding free places to dock
I assume you will be coming in from the C&D canal, so I will start with the upper bay and work south mentioning a few possible stops.
I like Harve de Gras it isn't the best sail in because of lots of shallow water
and only a narrow channel in, so usually you motor
for a few miles. You will find a nice place to anchor
just past Tidewater Marina on the left. There is a floating public dinghy dock
there and it is a nice town to visit. There are lots of good places to eat and in the warm months there is usually something going on at Tydings Park on the weekends. There is a nice little museum near the Concord Point Light.
I haven't explored the Elk or Sasafrass rivers, but I have heard good things especially about the Sasafrass.
Further south on the eastern shore, Worton Creek is a nice quiet anchorage and just below that is Fairlee creek. Fairlee Creek is more of a party atmosphere especially on the weekends. There is a golf course and a tiki bar among other things. The entrance is a little tricky though.
To the west the creeks off of Middle River offer sheltered anchorages
with places to eat etc. If you are into aircraft a stop at the museum at Martin State airport
may be worthwhile.
Back to the eastern shore, Rock Hall is a nice town to stop at. Either anchor
out in Swan Creek or pull up to the dock at Waterman's Crab House in the Rock Hall Harbor. I have often spent the night there. They don't seem to mind if they aren't too busy and you eat there.
There is lots to see in Baltimore
. Stop by the visitors center in the harbor to get some clues of where to visit.
St Michaels is another stop worth making. Anchor in the harbor or out on the Miles River. There are lots of little shops and stuff there. There is a nice Maritime museum and plenty of places to eat. If you carry bikes there are some nice rides there. Various length loops are possible using the Oxford Ferry
to cross the Tred Avon
. Riding to Tilghman Island is supposed to be nice too but I haven;t done that one.
Annapolis is a nice place to visit. There are slips and moorings for a fee, but we anchor off of the Naval Academy in Spa Creek where it is free. It is a short hop to the dinghy
dock on your right just past the Naval Academy property. From there you can walk to most of the sights in Annapolis. A harbor shuttle is also availble, but we haven't used it.
Further south we like the West and Rhode river area. The Rhode offers a nice beach and good anchorage, but not much in the way of shoreside attractions. Nearby Galesville (on the West River) has places to eat and reprovision..
Solomons is a bit farther south and worth a visit. There is the Calvert County Maritime Museum, places to eat, and you can find fossils (sharks teeth etc. at Calvert Cliffs).
That is a sampling based on a few of the places we have visited. There are lots of other places to visit, enough to keep a sailor busy for a long time.
I suggest that you buy the Gunkholers Guide to Cruising the Chesapeake and maybe also Tom Neals book (I forget the title).
Aurora (Alberg 30 #554)