Question: Mapping Software That Tracks and Links to Where I’ve Been?

Bruce Frank asks a question that rings a bell with me, but I can’t put my finger on it:

I’m looking for mapping software that I can edit and add my own tracks (places I’ve been) when I’ve made deployments with the US Navy. I want to be able to place a pin on a country, have a link to that map and then to a city where anyone can click the city link and go to the appropriate pictures I have on my web site.
Any ideas? Not sure what to call this type of map software but I’ve seen something similar used for commercial web sites.

I remember seeing something along these lines on at least one blog’s sidebar, but it disappeared a redesign or two ago. Maybe one of you can help with that.

It sounds like Bruce is looking for something along the lines of pointMapper (which I blogged in 2003, when it was called “*mapper”), or MapMemo if it had a web export component (see previous entry). But I could be completely off-target. What do you think?