All good points.
T37Chef - We have a pseudo-dinghy. It's actually an Intex Seahawk II inflatable. It will carry 2 men comfortably - 3 men provided they leave their shame onboard the sailboat. No outboard, only oars. With that said, we don't have shame and can therefore squeeze all 3 guys into it.
How far of a paddle is it from the mooring fields to the dinghy docks?
Also, thanks for the Oxford suggestion. I hadn't really considered smelling the roses along the way. I just assumed that we would be hard pressed to make it to Annapolis and back given our time constraints. From the comments listed it appears as though making the round-trip should be easily accomplished.