The most important thing to do, even before booking a flight, is to learn the basic geography of Italy. Get a map of the country, sit down with a glass of Chianti, and familiarize yourself with the regions. A lot of people for example, think that Tuscany is a city when instead it is one of the regions whereas cities within the region of Tuscany include Florence and Siena. I have been fortunate as I’ve travelled Italy solo, with Italians (mostly with my musically-gifted husband, see video below), and also with a guided tour. These are all fantastic options. I would recommend planning your travels yourself if you’ve had prior experience travelling throughout Europe and are a highly flexible and resourceful person. Italy is not the most organized country in the world, in fact, it’s rather infamous for lateness, transportation strikes, and general bureaucratic chaos. Even if you plan your days down to the hour, you can be assured that you’ll run into a metropolitan strike in Rome and be forced to find a Plan B to get around for one or two days. Having a general idea of alternative routes will be advantageous for your trip, along with just having a good sense of humor and willingness to live in the moment!
Once you’ve picked the regions you want to check out, the next step is to choose the cities or towns to see. I’m personally not a fan of doing the whirlwind Italy trip, trying to hit every famous city in one vacation. Some people may justify doing this with the excuse that it’s a “once-in’-a-lifetime”, but trust me…you’ll be back! I generally advise people to stick to two regions for a two-week trip, in this way, you can really get the true experience and immerse yourself in the regional culture. If you’re not sure what I mean by this it’s that each region has its own cuisine, dialect, and traditions that are very diverse. The dialects are so different in fact, that someone speaking pure bergamasco (the dialect of the province of Bergamo) may not be understood by someone speaking napoletano (you can guess where they speak this!). My absolute favorite regions are Tuscany and Campania. Tuscany for its postcard-perfect rolling hills and vineyards and that Tuscan light that gilds the landscapes at sunset, Campania for the stunning coastline (this is where you will find the famed Amalfi Coast), cliffs, lemon groves, and colorful towns that seem as if they are going to fall into the sea. Don’t let me sway your decision though, it all depends on what you enjoy seeing. Art history buffs will want to gravitate toward Florence, history fanatics towards Rome or Pompeii, and fashion lovers to Milan, so to each their own!"
All these choices sound daunting I know, but you can always check out an online resource such as GoEuro where one search allows you to find and book the best travel options by train, bus and flight!