ManicWolf

If you make up your mind to do it, feel free to be my guest in Rome, literally, for as long as I am here (I hope to eventually return to Milan, but it won't be anytime soon). I rent a decent-sized apartment very centrally and have a sofabed in the living room. Objectively speaking, I'd say that Venice is the most striking of the three cities, but my personal favourite place in the world is Lake Como an hour away from Milan, so while Milan itself is not a spectacular tourist destination (despite my subjective love for it), it is worth a stopover to go to at least one of the lakes (Como is really the best) at least for a day trip - which is best done between Easter and the end of October as there are more boats running. Rome is pretty much OK all year round with minor variations due to weather etc, but I'd say that unless you are a museum fanatic, you can easily see most of it in 2-3 days.