We decided to do Italy for a month on our own. Saved about $3,000. Yes it took a lot of time and coordination. Traveling Italy by train between cities can be a challenge with their train systems. Once on board ( one to the two main train companies) is not bad using high speed rail. But the train stations can be chaotic and crowded. Use of Uber and/or taxi was great. In general, we found that Italians are not the friendliest people on earth, at least to Americans, but not outright rude. Florence was the worst. We should have stayed in the Tuscany region instead.
Our trip included Milan-Lake Como-Belagio-Venice-The Dolomites-Cortina-Ortesei-Florence-Pisa-Rome-Sorrento-Amalfit Coast back to Rome Airport for our flight back to the States.
Best advice: If from the States......don't expect the same service. Everything is on half-speed. So, relax, drink and eat. The food is fantastic. Our best restaurant was (Ibisco) in Sorrento. Excellent food. Salads were fresh, crispy and tasty. The bass was the best I've every had. Highly recommend.