Depends on what you are looking for.
The southern bay offers Norfolk, Hampton or Cape Charles on the eastern shore; I think each is worth a stop.
Yorktown is a good stop for history buffs with Williamsburg and Jamestown a short drive.
Deltaville is loaded with marinas and yards if something breaks down and there is a new West Marine in town. Or stay on the east side and stop in Onancock (see below) before heading to Tangier.
Tangier is a step back in time and worth a stop, I'd approach from the east. But dock space is very limited so have a back-up plan.
We were in Crisfield last summer for the 1st time in a dozen years and were shocked at the changes. The town saw some of the mid 2000 building boom and a lot more of the downturn. The town marina is Ok but the property is surrounded by a fence for a reason. I would bypass the town and visit Onancock; a quiet little town on Va's eastern shore; couple of nice restaurants
and other sites. There is a small marina or several anchorage sites.
St Mary's, MD is up the Potomac about 12 miles and another 5 miles up the St Mary's River. Interesting archeological site and a good anchorage, no dockage.
Reedville has some nice anchorages and a couple of marinas. There are two good places to eat and a 1st class museum. But I would be aware of the wind direction as the menhaden plant can cause one to lose that good dinner if the wind is out of the east.
You did say you were planning to stay in the bay for a month didn't you.