This was my solution:
Friends and family laminated map stickers!
When I finished making the stickers. He could not wait to look at them. This surprised me a little because usually when I work on something like this for him it takes him a little while to appreciate it...if at all. This time he carried them out to the car and looked at them all the way to our destination and back. Yeah!
The 'how to:'
1. I sized and cropped pictures of friends and family we visit often (and happen to have pictures of!) using Photoshop.
2. I laid out all the pics (sized to .85in circles) in Illustrator and printed them all at once on photo paper (I tried cardstock first, but they weren't clear enough to tell who some of the people were).
3. Cut out circles. I wish I could have found my large holepunch for this, but my not-so perfect hand cut circles work just fine (or so I am trying to convince the perfectionist side of me).
4. Laminate circles. I used GBC SelfSeal laminating pouches.
5. Cut circles out of laminate.
6. Put through Xyron 150 Create-a-sticker. You could use double stick tape here too. Or if you REALLY wanted to simplify the project you could print the pics on label sheets and eliminate step 4.
Now your stickers are ready to place on their proper map locations!
WARNING: After placing all 24 of my new, indestructible stickers on the map, I so proudly presented it to Jon to show him what I did at naptime that day...he quickly took the wind out of my sails by pointing out that the maps are no longer useable because the pictures cover up parts of them map...whoops! I was so caught up in the details of my project, that point didn't even occur to me. So if you decide to do this project, you might want to buy new maps :0)
You could also use this idea on a full size map of the United States (or world, or city) if you have family and friends all over and hang it in a playroom or bedroom!