Harve de Gras and Sassafras are close to home for you and you can do that anytime. My suggestion is to travel "down " the Bay. 20 mile clips are as follows.
First stop could be be Still Pond or our favorite, Whorton Creek. Which ever one you donrt hit going down...anchor in on the 6th night comming back. Thats less than 20 milews or so from Bohemia
Second night could be Rock Creek (where Chef37Tartan ) and I keep our boats or Rock Hall. Again 20 miles and hit the other one on your way back on night 5. Rock Hall has a great Crab restaurant.
Third Night could be the Magothy and Eagles Nest or Mill Creek with Cantlers Restaurant
Fourth night- Annapolis
Fifth Night- Rock Hall
Sixth Night Still Pond/ Whorton Creek.
Also there is the Chester and St Micheals as another alternative to the Bay with a trip through the Narrows.