I'd go with the Annapolis - St. Michaels - West River
route. Winds are generally out of the south, so getting to St. Michaels will take some time tacking down the Bay.
St. Michaels is a nice town with things to do - the Maritime Museum, many shops and restaurants, a winery, a brewery, etc. There are a couple of
marinas and you can also
anchor out. Long walk (or short Uber) ride to grocery and
hardware stores.
The trip from St. Michaels to Galesville/West River is easy. You can anchor in the West River. There are also a couple of marinas (Pirate's Cove & Hartge's) that have transient slips. Two restaurants are an easy walk from Pirate's Cove and a moderate walk from Hartge's. No stores to speak of. Easy to get back to Annapolis in half a day with a southerly breeze.
If it's your first time here - I'd avoid going through Kent Narrows. It's not the easiest or most fun stretch of the Bay.
If the above doesn't appeal - I'd also consider going to Rock Hall and then to
Baltimore Harbor - but I don't know the status of entering
Baltimore since they may still be working on the bridge.