A friend did this last year (during a long stint of unemployment). Mostly couch surfing and bumming rides from friends.
She seemed to have a blast. I want to say she "visited" 17 different cities. Visit being defined as some stays only lasting 4 hours, others a few days. She used it to visit a few places she had not been to yet, and also to interview for some jobs across the nation, to attend a national trade convention for her profession (and interview while there) and also to meet with grad school friends that are now spread out all over the country. For the price of two domestic plane tix, it was a really good deal for her.
Recently retired at 33. Loving it so far! Wife is still working for ~1 year. I'm secretly just a stay at home dad with 3 kids (1, 7, and 8) but don't tell anyone.
Money is the Root of All Good.