this is a wicked cool idea and you should do it. This is what I did for a while in San Diego but I most stayed in one spot. I also had a few buddies who were with me and we just surfed everyday. Sometimes working odd jobs for cash. I have done that for a month were I live now and love it. I have people I know to hang out with so it doesn't get lonely. Its what I am going to do this summer even if I get the job I want.

edit: After reading some more post I decided to change the tone of the advice. Its not glamorous at all man. If anything you should look at train hopping or the AT. I only do it in the summers cause I can, I am not old at all and can afford to in more ways than one. I dont do winter cause I find it...not fun..oh and plus I love to ski.