You should try getting around in Boston. A lot of the streets aren't signed and even if they are signed, the name of the street is likely to change every few blocks. Plus there is no grid; everything just curves. That is both Boston's charm and curse.

A gps is helpful. So is a kind of dead reckoning by relying on landmarks to figure out whether or not you are more or less going in the right direction. Use a paper map to figure out what the major landmarks and get a sense of direction. The gps may be largely idiot proof but isn't much help in orienting you in space.