re: If you have taught in a foreign country before.

You're looking to pay $2,200 to teach a family English? I'd recommend not doing that. I was just part of a program that paid me about $1,000 per month for 7 months to teach 12 hours of English per week at a French high school. Other countries have similar (and less competitive) programs.

Are you a student, that's why you want to do it in summer? I'd suggest spending that time to develop a foreign language, then spend the year after graduation in a country that speaks that language.

I'm not sure about Italy, but I've been checking out similar Spanish programs and found this useful site LINK. Might find it useful if you're open to going to another country.

edit: I see you are paying $2,200 in addition to the flight. Don't do that. Do some research and teach somewhere that will pay you, not the other way around. Opportunities are there.