Getting to Italy is a harder than most would expect. If you are an American, Canadian or Australian, you do not have the right to work or live in Italy. Because of this you need to find ways to work around the obstacles that governments and history have put up. When we say getting around obstacles, understand that we mean in a totally legal sense. Since there are ways to do things legally, there is no reason to do things illegally. The cost is too great: expulsion from Italy.
One of the easiest ways to get to Italy is to have citizenship from an EU country. With that, you have the right to live and work in Italy and your spouse and children have the right to follow you. You will still have to deal with paperwork and bureaucracy but you don't need to get visas which is a huge saving in time and stress. Having Italian citizenship allows you to avoid lots of red tape too.
Another good way to get your foot in the door is to apply to an accredited school while attending a university program in your home country. Armed with your student visa, you may legally work 20 hours per week. This may not be a lot but it is a start. You can make contacts and maybe one of those contacts will hire you and do all that is needed for a work visa. This kind of visa can be issued provided you have proof that an Italian school has accepted you.
Living in Italy also means paying the Italian taxes, such as the canone Rai (television licensing).
Visas for non-EU citizens or retirees
If you are not an Italian or European citizen, you must get a visa to stay in Italy more than 90 days — in total, even discontinuously — out of any 180-day period. After your 90th day, you must leave the European Union for 90 days (three months) before going back to Italy and starting over.
First of all, any visa is issued by the Italian consulate that covers the area where your home town is located.
A work visa can only be issued if you have found a job in Italy and the company that hires is willing to sponsor you by supplying all the necessary documents to help you get the visa. The whole process is similar to the US one (for non-US citizens).
On the other hand, if you are a retiree, things are easier. You will need to apply for an extended stay visa, or long stay visa, 90 days before you are planning on leaving. You will need to have proof of a place to stay, proof of an income to sustain you, medical insurance, a letter stating your reason for the move and a document from the police stating that you have never been convicted.
You can ask for an international driving permit before arriving in Italy, for example in the US.
If you have pets, be sure that you made all the arrangements even if you are an EU citizen.
How to obtain the Italian residenza (residency)
Visit your municipio/comune (City Hall) and find the anagrafe office. They will need your passport and permesso di soggiorno (the latter is not necessary if you have Italian or European citizenship). Some towns may request a rental contract. Your information will be entered into their computer, the application will be printed out, and you must sign.
Next comes the wait for the local police to visit your address, that is to say your new residency. Sometime in the coming weeks, they will make an unannounced visit to confirm you actually live at the address. A few days after they visit, pop by your anagrafe and see if your residenza is complete. If so, they will print you a certificato di residenza — useful for many things, such as signing up for health care, getting a driver's license if you don't have an international driving permit, reduced utility rates, etc. You may also apply for a carta d'identità, which is a handy photo ID stating your name, date of birth, home address and nationality.
Please note that residenza anagrafica — as described here — is a different concept than residenza fiscale, i.e. tax residency. Tax residency is beyond the scope of this article; please consult a tax expert or commercialista for details specific to your circumstances.