Don't forget the west side, although more populated it's got a few good spots:
Bodkin Creek - down near Prop's Restaurant and they'll pick you up for a taxi ride to eat.
Magothy River - many good anchorages - behind Dobbins Island, Broad Creek, Eagles Cove. Good restaurant at Deep Creek, good tiki-bar at Ferry Point.
If Annapolis is too crowded for you Mill Creek is a good alternative and has Kantler's to eat at.
Lessons learned are opportunities earned.