Second time you said this.
Not sure where you went sailing on the Chesapeake. Was your Annapolis experience your only one.
It was just a short sail out of Annapolis. But we were about 20 minutes out of port and still watching the depth. The skipper ran aground in what looked like to be in the center of open water. And when we took the water taxi in the evening, the pilot had to stay very clear of shore to come around the bend.
Very limited experience, yes, so my opinion should be taken with less than a grain of salt. But I still loved being there.