OK, come to Annapolis
, put in at Sandy Point State Park.
to St. Michaels on the Miles River using the route around the south end (Bloody Point) of Kent Island and stay over at least one day. Include the Chesapeake Bay
Maritime Museum as quality time at St. M's.
to Kent Narrows, on the east side of Kent Island, stay for lunch or even overnight; several good restaurants in the area.
Cruise to Rock Hall, north of Kent Island (past Love Point) and stay over at least one night. Stay in either the main harbor or the Swan Point side, enjoy the restaurants. Main Harbor a bit more partying type, you'll want to honor the day marks around the horsehoe upon entry.
Cruise to Fairlee Creek, further north on the eastern side, and stay over a night. Anchor
out if you like, but enjoy the tiki bar.
Come back to Annapolis
and stay in the harbor area -- slips in Ego Alley, on the moorings (water taxi service
is easy), or at one of the other marinas
. Sta over one night and party in downtown Annapolis.
Run back to Sandy Point for departure.
I can modify all that easily, with stops in Deale, Chesapeake Beach, Solomons, Cambridge, Oxford, Georgetown
, Havre d'Grace, Chesapeake City... and/or lots of decent anchorages
But you'll want time to do stuff when you get to places, and you'll probably want some "hang out" time... so this was just a start for initial consideration.