Learn

For English-speakers looking to study in Italy, there are a few options. In Rome, Duquesne University, John Cabot, and Temple University maintain campuses. Right outside of Rome the University of Dallas maintains its own campus in Marino. Penn State University has a program that sends architecture students. St. John's University has a graduate program in Rome for International Relations and MBA.
It depends on how you want to learn. Are you interested in studying in a huge touristy city like Florence or Rome? Or, are you interested in learning from a small town on the Italian Riviera. The smaller cities have better opportunity to learn Italian because there's not a lot of English going around. No matter where you decide, Italy is one of the best spots geographically to travel while you're not studying.
Think about learning what the Italians are best at: food, wine, Italian language, architecture, motors (cars and bikes) and interior design.

Work

Work in Italy is very competitive. Unemployment rate is considerably high, compared to other major European countries, and mostly made up of young adults and female. There's a huge underground black market though, where you'll find most of these individuals working. This doesn't mean working in some kind of obscure crime syndicate: most "black" workers can be found in small business as bars, pubs, small shops or construction workers. Although this kind of jobs are illegal (but legal consequences are most on the employer) they're probably the easier thing to find if you're looking for a temporary job.
If you're thinking about establishing a small business be sure to get in contact with local Chamber of Commerce and an accountant and they will help you sorting out the mess of Italian laws, and such.