Pittsburgh: I recently spent some time there and was pleasantly surprised. Then again, my expectations were pretty low. I expected a rust belt wasteland, akin to Buffalo or Cleveland. Pittsburgh turns out to be a charming, completely unpretentious city with decent food, and and music. It's the sort of place that I can live in at 35, but would have hated at 25. Portland, ME: There's a definite Austin, TX vibe there.