Consider to go a little 'lower' on the Bay
Harve de Grace, the Sassafrass, the Bohemia all require long 'motoring' trips in the rivers and thier approaches (~1 hour additional) to get to the 'bay proper'. On all of these rivers you will be constantly subject to running the gauntlet of being 'waked' by stinkpots in the rivers and restricted/narrow channels. Being in the far northern bay restricts you to only go 'down' the bay. The water quality at the head of the bay (@ Aberdeen & Sassafrass) is quite polluted usually in midsummer with toxic algae blooms, etc. From all those rivers your anchorages for when sailing 4-6 hours max. will be limited to 3 principal (usually overcrowded) places: Ordinary PT. on the Sass., Still Pond, Worton .... and rarely anywhere 'lower'. Traffic on I-95 (your access to this area) can be gridlocked on weekends by cars waiting to get through the multiple toll boths at the MD/Del border... 3-5 mile backups, Rt. 40 is full commercial, bumper to bumper and has untimed loooooong interval traffic signals. For that typical 1 hour 'boat-drive' in the upper rivers from these places to the 'open bay', you can drive your car in 1/2 that time to Rock Hall, Tolchester, Fairleigh, Worton, etc. on mostly uncrowded roads (Rt 1, 896, 301, etc.) and have double-triple the choice of sailing venue (in multiple directions), probably 3-4 times the areas to anchor/gunkhole nearby with 4-6hrs. sailing time, less traffic, close access to the 'hot-spot' destinations: Annapolis, Baltimore Inner Harbor / Fels Point, St. MIkes, etc. etc. etc. etc. Most folks usually only stay on those upper rivers a year or two, then usually move 'lower on the bay' for better access and venue, etc. Less moorings lower down and slip prices are higher; but, with all things considered you will have less hassle and a vastlly better sailing venue/value. Your choice: being stuck in traffic on I-95/US40 and then 'motoring' in your boat for an additional hour to the 'bay' or driving 1/2-1 hour longer and being ON the bay. Hope this helps