I don't this to come off as rude but we bought a Doziers Chesapeake Cruising guide. I thought this was money well spent as it is pretty detailed about available marinas etc. Anchorages,etc Our photo album has a Chesapeake cruise which for the northern end has a nice selection of places with pictures of where we stopped last spring. Since there is about 2000 miles of shore line on the Chesapeake there is a lot know. There are countless places to duck into in the event of a thunderstorm etc. Active Captain has this area covered pretty well if you don't already have an established account I would review there info as soon as you can. A lot of places get crazy busy with lots of people on the weekends so be prepared to move on as your first choice might not be available. Rock Hall, Saint Michaels, Worton Creek, The Saasafras River into Georgetown,along with the Wye River, the Severn River are beautiful places with many options for the individual rivers themselves.
D.D.