Illegally Teaching English in Italy Legally

The Curious Case of Benjamin Boston

Part one in a 2-part series assessing the legal hazards and risky loopholes for those wishing to teach English in Italy without proper EU work permits

By Eliot Stein

Things are rarely black and white in Italy. From Botticelli to Berlusconi, Italians are famous for muddling their palettes and coloring outside the lines to serve their personal vision. The result is a chaotic cultural canvas where creativity can circumvent bureaucracy for those dreaming of transitions abroad.

Add a 30-hour workweek, tumbledown bucolic villas and mouth-watering cuisine and it's no wonder that Italy's delicious lifestyle leaves Americans salivating with wanderlust. While the process of obtaining an Italian work permit is thorny enough to keep most non-EU citizens at home, many others throw caution to the wind and pack their bags without a freelance work visa every year—convinced that with some creativity and a little Italian “furbizia,” they can slip past the red tape and earn a living. After all, "When in Rome…”

That was Benjamin’s mentality. Fresh out of college and still detoxing from a semester in Tuscany, the wide-eyed Boston native clung to romantic notions of La Dolce Vita. Like many aspiring expats, Benjamin was determined to follow his mother tongue across the Atlantic and land a job as an English teacher. He made all the right initial moves while still in the States; first receiving his TEFL certification, and then sending cover letters and résumés to schools seeking teachers on sites such as ESL Cafe during their prime July to September hiring season.

As an American citizen, Benjamin knew he faced an uphill battle in the job market since Italian employers are legally bound to offer positions to EU citizens. Each day Benjamin found polite rejection messages in his inbox sprinkled with curious phrases like “our colleagues discourage us from bringing you on at this time,” or “we’re told it isn’t prudent this year.” The emails only came from schools in highly-populated cities, while those located in smaller towns didn’t even bother to respond.

Benjamin eventually received an offer from a well-established school in an Italian city willing to “unofficially hire” him. After the school’s director assured him multiple times that he would receive the same wages as his British peers, Benjamin bit the bullet, agreed to work “in nero” (under the table) and bought an open-ended plane ticket. Ten days before his flight, he received an unexpected email from his “unofficial boss” shedding some light on the obscure third-party warnings other schools had referenced:

Dear Benjamin,

I was informed today by our private contact at the Italian labour office (Ispettorato al Lavoro) that we are definitely going to be having a full inspection from them sometime between October and November. These inspections are usually made without prior warning and last at least three days, during which time the inspectors seal off the doors and check on every single person working and coming in and out of the school.

If we have you as an American citizen working with us when the inspectors come we will not only be fined for having an unregistered employee but will also be liable for criminal charges.

These inspections don't happen that often and that was why I was planning to have you working with us "unofficially" this year. But now that I know for certain that we are going to have these labour office inspectors swooping down on us sometime in the next two or three months, I am no longer able to have you working with us. The risks are really too huge for us and for you as well. If you were here when these people came in the door and sealed off all the exits, we could risk enormous fines and legal action. Fortunately, the labour office doesn't inspect schools that often so your chances of ending up in a school that has an inspection are really very slim.

Regrets and best of luck to you.

Weighing the Legal Risks

Benjamin’s telling email and trying situation reveal important truths for non-EU citizens yearning for an ESL life in the Bel Paese. If the risks for non-EU residents trying to sidestep the Italian labor office are both “huge,” and also “really very slim,” how can others translate this contradictory cobweb into practical information? Like any crapshoot, it helps to know your odds before you play.

According to numerous private English-language school directors in Italy, local labor offices inspect their businesses every 2-3 years. While common sense might lead non-EU teachers to seek “in nero” work in more remote Italian sanctuaries, less-populated areas actually maintain more rigorous labor checks than metropolises. It’s also easier to slip under the radar in larger cities where—if we’re to believe the emails Benjamin received—established language schools often communicate with labor offices to avoid fines, acting like a de facto watchdog for illegal teachers. This notion extends beyond the ESL labor force and helps explain why far-flung Sardinia has the lowest per capita rate of foreign-born residents in Italy, why Milan, Rome and Naples are inundated with extracomunitari (non-EU citizens), and why Benjamin couldn’t get a response from schools in isolated areas.

What about overstaying your welcome? American citizens are legally allowed to stay in Italy for up to 90 days without needing a visa. Gone are the days when backpackers could hop a train to a non-Schengen country one day and return to Italy the next day with a renewed 90-day stay. As of 2007, Americans who choose to bypass the hurdles of obtaining Italian work permits are only allowed to remain in Italy for a maximum of 90 days for every 180 days (that is, if you arrive on January, 1, you can stay until March, 31 at which point you are technically required to return to the States for 90 days before starting a new 90-day stint in Italy). However, as John Moretti, author of Living Abroad in Italy writes, “Italians are much less worried about Americans overstaying their welcome then other nationals from outside the EU,” but warns, “don’t take this as an open-ended invitation.” Speaking on the condition of anonymity, a representative at the Italian embassy hinted, “Italy is not out to make war with Americans. Just don’t be foolish.”

Benjamin was foolish. With a one-way ticket in hand, he decided the Italian siren song still outweighed the bureaucratic pitfalls and quickly found another ESL job in nero. He overstayed his 90-day tourist visa by three months and disregarded the mandatory U.S. return. Yet, Italian immigration authorities never blinked an eye. Beginner’s luck, so he thought. After repeating this pattern for nearly two years and meeting other non-EU English teachers who had conjured up creative ways to circumvent Italian labor bureaucracy—some successful, some not—he was starting to realize what American expats had learned long ago: things are rarely black and white in Italy.

Part two of this series on Illegally Teaching English in Italy Legally explores how to relocate to Italy on a shoestring and three common ways to work under the table.

Eliot Stein is a freelance writer and photographer. He feels at home in Washington, D.C. or Italy, where he has taught English at numerous language schools. He is the author of Footprint's guidebook to Sardinia.