Old people in Italian villages, especially men, spend lots of time on the street. I really enjoy engaging them and making portraits where they stand. Spy pictures with a telephoto lens are fine, but I prefer face to face confrontational portraits. I like the energy that's exchanged between the viewer and the subject when they are aware of one another.
The question I hear a lot is "How do you get people to pose for you?". A few tricks come to mind. First, I try to strike up a conversation first about something else besides pictures. Having the camera slung behind me instead of in my hands helps. Obviously, speaking the language helps too. But even if you can't speak Italian, you can ask directions or for the nearest market with gestures and smiles. Italian people in small towns are extremely gracious, and you can ask for a quick photo as a measure of your thanks.
I love to approach older men on the streets and ask about the history of their town. Notice that most of my portraits are of men, because I find the older men have lots of time and little to do. Women are usually heading somewhere and are more self conscious. Questions about where they're from and what they do for a living usually break the ice and allow me to ask a favor of them. If my first question is "Can I take your picture?" most people are going to say "No thanks."
For portraits I usually start with these settings: Aperture Priority, ISO 400, F/2.8 with a focal length of 50-85mm. Of course the best lens is the one you have on, because you rarely get more than a minute or two from these sessions, but if I had to choose just one lens for street portraits it might be a 50mm F/1.4, so I can stay close to my subject and because it's not too intimidating. To photograph an individual, I'll choose the widest aperture possible to keep the background out of focus.
It's scary to approach people for a picture, but it's often the most rewarding experience of your trip to Italy.