You could write a letter about what live is like here and what you like to do. Then ask about Italy and where he's from in Italy, translate it to his language online, and there ya go:) hope this helps!
I would write a letter saying what the USA is like, and tell the person a bit about yourself. And i would also send a little souvenir that might be hard to find in Italy. And ask them a few questions.
I wouldn't translate it into his language online if he knows English. Translators are no where near perfect.
Send them peanutbutter :) When I was in Italy I missed that a lot. It's SOOOO expensive there it's absurd =/