Actually, I did this already and have been here for the past ten years. In my case, there really wasn't a choice of where to move. My job moved here and I came with it. However, I really like living in Mirandola. It's a nice small city with convenient connections to Bologna, Verona and beyond using the trains. We are only two hours from either Venice of Florence. For the size of the town there are a lot of activities and festivals - this is a center for the medical device industry. As with everywhere else there aren't necessarily available jobs right now though. There are many other very nice places to live here though. What's right for you would depend on your particular preferences.
You do need to know that living and working here isn't easy if you're not an EU citizen. EU citizens have the right to live and work within the EU, but others need a visa to live and work here legally. You can't just decide to relocate to Italy and go; it'. The site for visas here in Italy, for example, 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/