St. Michael's is a fun place -- one of our favorites -- but it is not a destination that offers everything for everyone.
If there is a movie cinema or a theatre, we have yet to find it.
Pizza is a bit hard to come by. And unfortunately there is not a decent chandlery.
So those are some negatives.
But there are many positives too. Part of the fun is wandering around and discovering the shops and old buildings.
The gem of St. Michael's is unquestionably the Chesapeake Bay Maritime Museum (CBMM). If you plan to spend more than a day in St. Michael's, I highly recommend purchasing a CBMM annual membership (rather than a day pass/admission ticket) which will allow you to peruse the exhibits at a leisurely pace. In addition to many exhibit buildings, they have a working boat shop where you can watch on-going projects.
If you purchase a Contributing Membership, this will entitle you to use the CBMM docks and showers for overnights (reservations recommended). There are other private marinas, but in my opinion, CBMM has the best location in the harbour.
If you prefer to anchor out, your choices are to drop hook in the lagoon just north of Navy Point (part of CBMM). This is a very short dinghy ride -- oars only. If the lagoon is full (it's a small area), you might be able to anchor on the far side of the channel opposite the Hooper Straight screwpile lighthouse, but there's not a lot of space there either. Farther out in the roadstead (beyond G3 and R2) there's plenty of room. This anchorage has the advantage of more breeze, but can get choppy (even lumpy) and is a long row (outboard preferred).
There is very handy provisioning at the ACME grocery store. They will let you roll their shopping cart down to the waterfront. Also, there is a decent laundromat behind the ACME.
Have fun!!