Book Help - Searching for Title and Author

Hi. I’m hoping you guys can maybe help me.

There’s a big part from a book I read awhile ago that I can’t place and I think I want to read the book again. I was wondering if you could maybe help me.

What I can remember of it is that at one point, a guy in the book (I want to say he’s a main guy but he might not be) ends up in Italy. I don’t know if he’s in Italy because the Government sent him there after springing him out of prison or something, maybe or for another reason, but while he’s there, he’s given a “Handler”. He gets put up in an apartment or a hotel - and provided with a tutor to teach him Italian. He does pretty well - he studies quite far ahead and picks up a lot of stuff. I remember he and his handler going out to various restaurants and him being told that he had to handle the whole transaction in Italian. Also, the guy at one point has a “romantic interest” in a tourist guide that I THINK the handler has told him to use to get to know the country. For some reason I think there’s a sense of urgency about his getting along in Italian but I don’t know why. I have a really strong feeling the government is somehow involved, but I’m just not sure. I’m kind of an idiot as well so I could be totally misremembering the whole damn thing.

Help? Please?

Thanks,
,
M2U