A neat little web gizmo: Globe Genie takes you to a random location in Google Maps Street View every time you press the cheekily-labeled "Teleport" button. So awesome.
EDIT: I'm still sitting here clicking. I'd like to suggest a game I sometimes play with myself in the real world, especially when going somewhere new: Look at your surroundings in a given spot; if you had just been plunked down with no context, would you have any idea where you are? Using Globe Genie makes it possible to actually do this (there's even an on/off toggle for the locator map). If you have no idea at first, wander down the road a bit to look at that house...Peugeot in the driveway, can't be the U.S. Etc., etc. It's still fun even when you're totally wrong.