Should I chance working illegally in Italy?
Okay. Let's backtrack. The right to work in Italy depends fundamentally on your citizenship. In the broadest brushstroke terms it can be explained this way.
If you are a citizen of an European Union nation you are eligible to be employed in Italy. Example: You're an Irish national and visiting Rome; you're offered a job by an Italian company. You can fill out the paperwork, accept the job, and be legally employed. Example: You're a visiting U.S. citizen and see the job posted. Problem. You not eligible for it, can't take it, and even if the company that advertising the job wants you in it and is willing to sponsor and support your work visa application, you will still have to go back to the United States and make an application through the Italian embassy or a consolate.
Sidebar: Even EU citizens (or dual U.S.-EU citizen) still need to register with the police, get a residency permit, register as a worker and obtain a codice fiscale (tax ID number) once they’re settled in Italy. Getting a CF is the simplest of these demands, since it's much like a U.S. Social Security card and based only on your name and date of birth. See the Italian codice fiscale site. Enter your surname in the cognome field, name in the nome field, giorno means day, anno year. Comune/Prov is for your birthplace. The system can be fickle when it comes to foreign capitals, so try Roma or Milano instead — remember, all you want is the number.
But back to the situation itself. Americans shouldn't fool themselves. Working in Italy means obtaining the necessary documents before you arrive. Yes, you can fly in without a visa, as a tourist, but that has no bearing on subsequent employment. You cannot get here first and set yourself up later, as was once the case. You're either set up when you arrive or you're not.
Some companies will in fact offer non-EU citizens short-term contracts and ignore the law, but if you're busted you're cooked. You can be fined or expelled, or both. Many will say, but "How could I have ever known I would be offered that job? Why can't I just make it work from here?"
The system isn't set up to suit your good luck. It's based instead on the principle than citizens of non-EU states are not entitled to work in Italy unless they can prove they are doing sought-after duties that only a non-EU citizen can perform and that an Italian-based (or U.S. based) company wants them in Italy specifically to do.
Newer, stricter laws are also intended to push illegal immigrants from Eastern Europe, Africa and Asia into regularizing their positions. Italy is a frontier nation for illegal immigration. The political debate on the issue is intense.
The U.S. State Department puts it bluntly: "American citizens who have a job offer in Italy, or wish to work in Italy, either temporarily or permanently, must be provided with a work permit obtained by the prospective employer, and must obtain a work visa from the Italian Consular authorities BEFORE coming to Italy." See more at "Living in Italy".
There's also a strict quota system for the number of non-EU workers accepted annually by Italy, which means the wait for a work permit can take time, depending on whether the specific national quota (whether the U.S. or Albania) has been filled.
What does that mean for local (non-EU) English-teachers and tour guides? Read our lips. Without a work permit you're off the books and outside the law. Make no mistake: Many are, and have been for years. You can earn cash, yes, but you're vulnerable if you get sick, need police assistance, or are simply in the wrong place at the wrong time.
Again, there is no quick fix, no easy solution. You must find a company here willing to state in writing that it will hire you. This opens the door to applying for a freelance work visa (visto per lavoro autonomo), which is what you'd need to teach legally, for example. Emma Bird provides good practical advice at Transitions Abroad.
In any event, even scouting trip for work that yields an full-fledged invitation to work in Italy and a promise of documents to support the offer will still require a return to the United States while the appropriate paperwork is processed.
Students fall in a different category. Enrolling in an study-in-Italy program usually permits you to legally reside in the country for the length of the program (under a study visa arrangement).
What study status does not entitle you to do is be gainfully employed, for the same reasons listed above (no, you can't legally waitress). Your student status doesn't automatically waive the work permit protocol. Michael P. Gerace's "Finding a job in Italy" is another bit of useful writing on the subject.
If you think you might be eligible for dual citizenship, check out the ICGS site.
Don’t mistake the permesso di soggiorno you can get for a 90-day, non-resident stay for a work document. It is not. The famous permesso is merely a short-term residency permit that confirms your legal right to reside in Italy for three months (or more) as a non-working visitor. Though necessary, it has nothing to do with employment.
How does this affect tourists? It doesn't. Coming to Italy as a tourist for a seven-week holiday and a pre-planned itinerary is also different from deciding to break the ticket, stay on, live in an apartment and pay rent. Landlords are more demanding than they once were. Most demand proof of your right to be in the country (the permesso) or at least want to see your return flight documentation. Sure, some landlords will put questions aside if you pay three months rent ahead of time, but such situations aren't commonplace.
The question, "Is working in Italy without the necessary documentation worth the risk?" is destined to always meet different answers. Those who have managed to work beneath or under radar will tell you it's fully feasible, even desirable (fewer hassles). Those who have found themselves cross-examined by landlords or police will say otherwise. Unlike drunk driving ads in the U.S. that come with the message "You will be caught," the Italian situation has been an remains more ambiguous. Grey areas abound. What’s not ambiguous, no matter how you choose to look at it, is the law itself.