I would check http://everytrail.com as a starting point. It's aimed at taking GPS logs from devices and mapping/photoing it in a way you describe, but you can also manually do it all. I think it will do exactly what you want, it's a matter of how much work is involved probably though.

if you use geotags in your photos you might be able to find a flickr affiliated site that can take the geotags together and automate a map (if it doesn't exist, it should... and would be fairly easy their API is all available). Flickr itself will map out photos by location but doesn't really do a good job of putting a timeline together for it all... In fact I wish someone would create a site to do this via flickr. it doesn't seem that difficult, and it probably has to exist somewhere since the API is all public. http://www.flickr.com/map/ is their map. you can narrow it to your own pictures only by doing a search, but then I don't see how you send that link to someone to retain the preferences in the search you actually searched for.

ideally my perfect solution would take my flickr photo geotags and TripIt itenerary and mesh the two... anyone, anyone? ... It's probably a relatively easy project (both have APIs), I just have too many projects as of now.

the newish canon SX 230 HS camera has a GPS logger built in, so it will log your GPS coordinates throughout a trip and when you get back it will put it all on a map and do exactly what you want. I just ordered this camera for christmas. I'm kind of excited for that feature (though it's incompatible with the Eye-fi wifi enabled SD card which I'm also looking to get for that camera, so i'll have to pick). A friend has this model and the GPS fix itself can be hard to get from what I gather so I don't really know how much work is involved to have the GPS logger really being accurate, but if it works even based off of most photos I'd probably be pretty happy. (And this might be confusing to some, but I should point out that the GPS logger is different from the GPS itself, which will geotag a photo to record the location it was taken. GPS logger will log the actual trail of where the camera is, and can be turned off independently of geotagging your photos)