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Rome is easily one of my favorite cities in the world, and as others mentioned, Italy's train system (as long as you are taking the high speed trains, not the slower local ones) makes getting to other cities pretty easy.
This + getting to see a Roma game (didn't get to since it was out of season when I was there last) + getting to see my family in Milan = NO BRAINER. Guess I should start saving up now.
Funny story... I just got back from a 2 week vacation to Italy... and while I was there, there was actually a strike by train workers while we were over there and we almost got totally screwed trying to get from Lugano->Milan->Rome. The funny thing was that talking to other people on the train apparently strikes like this happen all the time and the trains are completely unreliable. Yes, this was on a "slower" one... and after we got on the high speed one in Milan it was no problem. But basically our train made it halfway to Milan and then they just shut it down because it was time to strike and we all had to scramble onto another train to a different Milan station.
Another funny anecdote is that when my fiance used to work in the Prime Minister's office in Rome her boss was an Italian guy who had graduated from BC. This game needs to happen... and the Pope needs to flip the coin for sure.