I have cruised single handed (or with small children, which is a more difficult variation sometimes!) on several boats, and many of the details are boat-specific. Single handed day-sailing should iron much of it out. It will also help that the Chesapeake is a pretty straightforward venue. Often the trickiest part is docking between the pilings, if it is a marina in a tidal current; instead, consider anchoring out or tieing along side, either of which is easier for the single hander.
I liked Tristan Jones "One Hand for Yourself... ", but remember too that he is a bit of a story teller. Still, he has a lot of good sense.
The most important lesson when single handing is to plan and to be patient. For example, if you are going to dock, circle by the dock first, make a conservative plan, get all of the lines and fenders deployed while circling in a safe area, then procede. Know your limits; if the current is too much, bail-out and anchor somewhere safe. Marinas will often send line handlers if you ask, but don't rely on them too much; some are good and some are green. Always have an anchor ready to go when near a harbor; engines fail and when alone you need to be able to park, to sort things out.
The sailing itself is generally simple. Work out the navigation before you start. Be conservative with reefing and weather. Use a harness and jacklines.
There is also information posted to my blog (below) and much more, of course, in my book:
http://sail-delmarva.blogspot.com/search/label/Circumnavigation Guide Summary
The Chesapeake is great cruising ground for the singlehander; lots to see and generally straight forward. I'm sure you'll have a great time.
