I have been wondering if there are mapping tools that let non-technical folks plot bunches of stuff on a map and either save it or ship it to someone. Of course there are. Matthew Hurst points us to Interactive Map Annotation From Ask:
Ask has relaunched their local search calling it Ask City (though the page is titled Ask Business Search).
For example, here are the plethora of coffee shops in the center of Evanston, IL, which I built by looking for the various business names that I know (don't forget to set pins between searches). One can also add pins for specific addresses. And I see it will calculate a route for you (walking or driving) from pin to pin.
I happened to be looking for something like this earlier this evening and came across Batch Geocode that lets you plot multiple addresses onto a map with a labeled pin for each address. The interface is a little clumsier, but with many addresses it is probably faster than the Ask model. One has to provide a tab-delimited set of addresses, but it gives you decent directions. This one happens to use Yahoo's mapping tool. The nice thing about this particular tool is that you can add things like the name and URL of the location (coffee shops) to each pin.
There are a bunch more of this kind of tool available via a search for "plot multiple locations".