I don't know Chesapeake specifics, but I have some ideas you might try.
Uninhabited islands, especially spoil islands, people generally don't seem to care much if you pull up a dinghy and set up a quiet camp in the trees. You could try google earth or land use maps. Basically, if no one lives there and there are no businesses there...
Or, you could try the British/French approach to dinghy cruising(which is also densely populated).. They actually turn their dinghies into little camp sites with boom tents, jet boils and just sleep in the cockpit/bilge of the boat on boards or whatever to keep them out of the wet. They seem to often let their boats dry out on the mud at low tide. It surely can't be as comfortable as sleeping in a tent ashore but lots of them do it.
You could check out Arwens Meanderings and Roger Barnes on youtube for some ideas.
You could look at the UK based dinghy cruising association web site for ideas. Dinghy Cruising Association - Home
There is a great book on the subject, also by Roger Barnes, called "The Dinghy Cruising Companion". I got my copy off Amazon. It's one of the better boating how to books I have read. It's pretty comprehensive.
There are also a couple of Dinghy Cruising Groups on FB. The bigger ones are UK based but have quite a few American and Canadian members because we just don't seem to have the same interest in small boat cruising over here that they have over there.