First, the tourist areas are where you're most likely to get by in English, but that would be as a visitor. The less expensive areas are likely to be in the countryside in the south where you're least likely to hear much English spoken.
This is difficult to do under the best of circumstances even with a degree and language skills; right now with the unemployment rates here, it is even more so.
Where are you coming from? Here in Europe, citizens of the EU have the right to live and work within the EU. It would be illegal for others to do so without a proper visa before you arrive. The site for visas here in Italy, is:
http://www.esteri.it/visti/index_eng.asp . The rules in much of the EU have been harmonized and will be similar. You can also check the website of the consulate that has jurisdiction over you for other information.
A work permit is separate - you cannot apply for that yourself. The company has to apply and they have to be able to demonstrate that there is not a viable EU candidate for the job. As a result, jobs for foreigners including Canadian or US citizens are pretty much restricted to people with special education, knowledge, or experience. The medical/healthcare field may have the most demand right now. Entry level positions in a field that you don't have any special qualification for would be unlikely - especially without knowing the language. When I applied for a visa several years ago, the process took about 8 months even though it was just of transfer of the job I was already doing from the US to Italy. Your best bet might be to work with an international company that has offices both there and here where you might be able to transfer. However, you wouldn't be able to do this as a temporary employee and you're not going to get room and board.
It's useful to check the expat sites for information about living and working here or other places you might be interested in:
http://www.escapeartist.com/
http://www.expatica.com/
http://www.expatsinitaly.com/
There are similar sites specific to just about any country you might be interested in that you can find by searching for "ex pat" or "expat" and the name of the country. Generally, these will have a lot of good information on daily life and negotiating the bureaucracy when you arrive and provide you with useful information you should know before you make the transition.
Right now, the economy isn't any particularly good and jobs are few and far between.
My one bedroom apartment here and my 4 bedroom house in Colorado cost about the same to maintain on a monthly basis. It's generally more expensive to live here than in the US. One other thing to consider if moving from the US - moving here to Italy doesn't relieve you of filing income tax returns in the US. You will also have to file here. It can be quite expensive.
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