Thanks, kd3pc! I'm hoping for a break in the heat by then as well.
I'm a bit concerned about the 40 mile leg - not sure if it's too ambitious. We'd really like to anchor each night as opposed to tying up in a marina. There doesn't seem to be a whole lot of anchorages on the western shore of the middle Chesapeake. Heading up the Choptank seems so far out of the way.