this is really great.
My advice to the original poster: skip winter at all: best in May, June, July, and best the centre and south
I would also advise to take the intense irrational reality you'll find as the best part of your trip: spend a lot talking to old ladies (65 and over), since they have no fear to talk openly
you'll be surprised by how conservative are the youngster: it is impressive.
I haven't been in the US in a while, but from recent news mentioned even here in HN, if you're visiting Italy from Seattle these days, you'd find the air in Northern Italy ( which is the worst in the EU ) actually an improvement, apparently ?
Same as if you come from San Francisco, looks like Rome or Naples will be safer from that perspective too. Local homeless, trash and litter, ubiquitous rude manners and insane murderous traffic be what they may.
Since you haven't been in Europe, may I also suggest to visit Spain, for actually friendly people and good food not so overpriced as the Italian, certainly not leaving without seeing at least Paris, and maybe look at some fairy tale towns and landscapes in central Europe; Czech Republic, Austria, Slovenia ...