I'm currently 16 years old and while I know that is young to plan a road trip it doesn't scare me. I know the issues and restraints I'm going to have to face with. That is the main reason I'm going to wait a few years before I start my big adventure.

My big dream is to see at least one town in every state (that can easily be reached by car). I've been consulting the net for a few weeks now and I haven't really found a good site/software to plan my trip with. Does anyone know a site/software that, if I type in a bunch of things or cities I'd like to see, gives me the easiest and shortest route? I know of Randy McNally's site and it's been slightly helpful, but the biggest strain is that you have to enter all stops in order. I want to be able to enter sightings as I feel like it and it will update my route automatically.

I know a 'cross country road trip is expensive and so I'd like everyone to know I'm not just jumping into this adventure; I'm planning this. I got 2 summerjobs this year, and I also work weekends at a bar. I don't have my driver's license yet (you have to be 18 years of age in Belgium) so this gives me at least another 2 years to save up money. I believe I'll have made a substantial amount of money by then which will allow me to make a carefree trip.

Now what I'm really looking for is people who can give me tips to make this trip. I'm making this trip with a friend who lives in Charlotte, NC. So we'd start out our trip there.
We want to see the clichéd sightings of course, but some off-the-beaten-path spots too. We'd be prepared to reserve a few days for the bigger cities like LA, San Francisco, Chicago, New York, etc.

People who live in quirky towns who say there's a really nice festivity there and who say it's must-see or -do please reply to this. I want to get to know the US; inside and out.

Thanks in advance,
Chloé