We chartered with Haven in Rock Hall this past weekend for three days and had a great trip. Rock Hall is a great starting point since there are plenty of great locations both North and South.
This past weekend we went to Harness
Creek off the South River on Saturday night and then St Michael's on Sunday night. Harness
Creek is really neat because there's a beautiful public park there where you can go for a walk and there's even a dock where you can rent kayaks and SUP equipment. You can also take a cab (or walk 3 miles) into downtown Annapolis. It was busy when we got there in the afternoon but it cleared out around dinner time. As for St. Michaels, there is tons to do/see/eat there so don't miss it if you head south from Rock Hall.
If you decide to head North then you can check out Georgetown or Havre de Grace. If you're looking for anchorages, Sue Creek off the Middle River is nice, along with Worton Creek and a bunch of places along the Sassafras River. Also even though it's a powerboat spot, the NW shore of Hart Miller Island is quite an interesting spot to anchor
for lunch. There are even food boats that will deliver right to your boat.
If you go with Haven Charters make sure you board the night before. They don't charge anything for this great service. Haven Harbor Marina is a nice place to spend the night anyway and Rock Hall is a neat little town. Have a good trip!