Originally Posted by
exilencfc
I can see where you're coming from but I don't think Rome is that bad. It's pretty easy to navigate around and most people speak English. Admittedly it has a bad reputation for pickpocketing but that can be avoided by not making yourself an easy target. Otherwise I don't think Rome poses any perils that can't be avoided through a bit of advance research.
That said, I haven't been to Milan and i'm quite prepared to accept that it's easier going than Rome.
Rome was the first European city I ever visited. You have to weigh my opinion against the fact that I speak Italian. Milan is probably easier, but I'm inclined to agree that Rome isn't too daunting. It's a global city, and anyone visiting it won't be the only foreigner and the only non-Italian-speaker. That said, when I left FCO to get in a cab, my cabbie didn't speak any English whatsoever! It does happen.
I agree with
ghiaaa's thoughts around taking incremental steps toward being a seasoned traveler. More generally, I also have the attitude that if my plane arrives in X city, and I've never seen X city, that I'm going to experience X city before moving on.