I've never been to Boston, though I'd love to.
DC is pretty easy to navigate aside from the traffic. I love the number/letter combos. So easy to find your way around.
Driving in DC is like, well, not driving. You're just parked.
Driving in Baltimore is like being in a drunken demolition derby. OMG trying to navigate Lombard on Thursday night, you better wear a helmet and make sure you have health insurance.
I have yet to find a restaurant in DC anywhere near as COOL as the Paper Moon up near Hopkins though.