Many Americans tend to stay in Italy without getting the permesso and Italian enforcement of this is sporadic-to-non-existent. Ignoring the law, however, might put you at a disadvantage. The rental agency or landlord who owns the apartment that you want may require that you get one. You will also need it if you go to the hospital or deal with the government or police for any reason. If it is your first time in Italy, then get a permesso as a tourist. You will only need your passport for this and, if you are an American, you will be granted an automatic 90 day stay in Italy. People from other EU countries also need permessi if they want to reside in Italy.

The biggest legal issue is the right to work in Italy as a foreigner, which requires a work visa. The hassle involved in getting one is a story in its own right, but the major hurdle is getting sponsored by the school that will hire you. It is an open secret in study abroad that many Americans work there “under-the-table” without a visa. The usual story is that you get hired first and then, sometime later, apply for a visa. The trick is finding a school that will hire you this way. It would be rare to find a school that would sponsor you for a visa without you first having a track record of employment there. There is already an army of people in Italy with the desire and ability to work in study abroad.