A wise old salt once said that there are only two kinds of sailors--those that have run aground and those that will run aground.
In five years with my wing-keeled, 4.5-foot draft Catalina 350, out of Back Creek in Annapolis, I have only run aground once, in the first season of owning the boat. It took me about 20 minutes to get free, but I did get free. I have bumped the bottom a couple of times entering Rock Hall harbor. If you pay attention to the
charts and the depth gauge, you should be OK.
I was considering a fin keel for this boat (5.5-foot draft) when I was in the process of buying it. My dealer indicated that I might have a hard time selling a fin keel boat in the Chesapeake Bay region.