go on a road trip with no destination

A friend from California (I’m from Illinois) are leaving early July for a road trip, the “epic” road trip to the “end”. We have no real destinations in mind except for the cities where we know people that will give us a place to stay for a day or two. Our real goal is to find a place that has abundant oppurtunities with work, (keep in mind we don’t have degree’s) living potential and hopefully somewhere that heavily supports fine arts. Both of us being artists (myself an American Academy dropout) Somehwhere new that has plenty of blue-collar work, so I can support my painting habit and work my way into gallery space. Cities that are tentative stopping points include Savannah, Tampa Bay, Providence, Toronto, Boston, and on the west coast Austin, Louisville, Santa Fe, Vancouver, Portland, and hopefully Boulder and Denver. Any one have ANY suggestions before our launch date of July 5th (leaving from Southern Illinois).