I mean, who wants to get tied behind a desk in a boring cubicle immediately after school? You are still young, you want to experience the world, live it up, do something different, and really Italy is just awesome. So, you say to yourself, where to start?
A job is a good place. Sure, maybe some of us can live off mommy and daddy for longer than others, but the majority have to have an income to support that wine-drinking habit that will inevitably develop. Problem is, you're going to run into a few brick walls here.
Firstly, your job prospects are severely limited. You basically get to choose between teaching English, working in a tourist pub, or being an illegal tour guide. For anything else, you have to (a) speak fluent Italian, (b) compete with all the other young unemployed Italians who are willing to work for less than you are, or (c) have some influential connections. If not, start looking for TEFL (Teach English as a Foreign Language) courses to throw a certification on your resume. There are lots of online guides on how to become an ESL teacher abroad.
Secondly, if you are American, Australian, South African, or just generally do not have a European passport, you will probably be working illegally. The English get all up in arms about this, but it's really just because getting the legal paperwork is near-impossible, something that they don't have to worry about. Now there are two possible responses to this assertion:
1. Living illegally in another country is unacceptable and I won't do it. I'll find a way to be legal. Well prepare for a battle that you will probably lose. The best way to go about this is becoming a student. You have to apply to a university, which means getting all your application materials translated, notarized and certified by the Italian consulate (you better learn what an Apostille is before even considering this), and then actually go to class and pay for a university, which kind of defeats the purpose of making money in the first place. If you want to throw a hail Mary and try and get an actual working visa, good luck. The Italian government issues a certain number of them every year, so you better have some serious connections or be working for a very influential company who really wants you and is able to go through all the legal loopholes to get you there. A typical English school will almost never do this for you.
2. Who cares? Italians love Americans, they need English teachers, so nobody will care if I just keep a low profile and fly under the radar. You, my friend, are in the majority. As uncomfortable of a truth as this may be, for all of Italy's illegal immigration crackdown, Americans (and Australians, etc etc) generally don't get included in that. Heck, many of the people I taught when I was in Rome illegally were judges, police officers and Carabinieri. As long as you don't give anyone a reason to arrest you and are very polite and and confident going through the airport, the majority of people don't have anything to worry about.
Now I am not recommending this, I'm just saying it how it is. If any weird situation happens while you are there illegally and you get Tommy-try-hard police officer on your case, you might be screwed. Generally, schools (and pubs, etc) will hire you. There are a lot of places that don't, but if you try for long enough, you will find a place to get hired. The fact is that English schools and tourism are big business in Italy and having native English-speaking staff is highly desired. Your paycheck will likely be an envelope filled with cash at the end of every week and that's that. There are other inconveniences involved in living illegally, like having a bank account (pretty much impossible) and getting health care (find the right doctor and you're set), but you'll generally get by.
So you still want to move to Italy after college? Go for it!