Oxford would be a great Eastern Shore destination worth the trip up the Choptank. In addition, you can get to St Michaels easily from Oxford, just follow the ferry
Its just about a mile walk if I remember correctly. The maritime museum in SM is very nicely done.
Just a thought...maybe a bit aggressive the first day...
Day 1: Yeocomico River to Oxford
Day 2: Oxford / St. Michaels
Day 3: Oxford to Annapolis
Day 4: Annapolis
Day 5: Annapolis to Rhode
Day 6: Rhode to Solomons
Day 7: Solomons to Yeocomico River