I am having a wonderful time with Worldographer, by Inkwell Ideas. I have been kicking out maps for my current campaign using the software. The image below is my campaign map (in progress) for just one city.
The City of Nace is made up of 64 insula, or blocks. I made a mistake by creating this as a battlemat. My reason was to have square blocks, rather than hexes. By completing a map in this fashion, what I will actually have is 64 individual maps. (Actually, 63 because the forum takes up two insula.) Each insula is 180 yards across, north to south and east to west. By the time I am done, my players will have over a square mile of gaming locations and I will have at least a vague idea of what is happening... everywhere.
I have barely scratched the surface of what Worldographer can do, but I figure this practice will help me master it someday.