Hi!
When I went to Italy I made the mistake of seeing only the biggest cities and totally burning myself out. My secod time I went there I still visitied the great cities (Florence, Venice, Rome) but I also visited the smaller historic towns such as Lucca and Sienna. It is free to walk the streets! And there is nothing more enjoyable. The Italien countryside and the small medieval towns that dot it are absolutely beautiful so don't miss it. If time is an issue I would skip Milan since it is mostly a shopping/commercial city. I think the above three cities I mentioned are worth visiting for the amazing museums, churches, and architecture that they offer. The best thing is not to pressure yourself to see everything, but just do what you feel, immerse yourself in the culture, relax and have fun! Also, the nightlife is amazing, but I just have to warn you that there are tons of cons in Italy that are aimed at tourists. Use real taxi's; don't take offers from random people on the street for anything, and always beware of your belongings. Public transportation is a great and inexpensive way to navigate around Italy. Their railroad system especially (as in most of europe) is excellent and my opinion the best way to travel long distances. The bus and trolley cars are a great way to navigate within the cities. The best way to see everything, however, is to walk! The most important thing is to have FUN and be safe. Hope you have a wonderful trip, I just know you will love it.
