In Firenze, thinking of the language issue, I have a couple rather humorous stories. As a primer for this, if you know Spanish (I'm on the rusty side of fluent), you've got something in the order of 25% of Italian covered. Not so much the other way round.
On the Piazza della Signoria, there is a little lunch place that sold panini and pasta. I went in for lunch, and did my best to order in Italian: "Une con salchiccha, per favore". In only modestly accented English, the clerk fired back, "That'll be 3500 Lira". She must have heard the Yankee under the Spanish accent, and had enough American tourists through to be able to spot me a mile away.
I went to this little restaurant not far from my hotel, which I picked in part because they had their menu posted out front in five different languages, including English. When I entered, the maitre d' seated me and gave me an Italian language menu, then zipped off to take care of an already seated table. Since, as previously noted, Spanish is not terribly far from Italian, I was able to read the menu reasonably well, and figured out what I wanted. When he returned to take my order, I asked in my attempt at Italian if he had an English menu, thinking if we had a problem communicating, I could always point out the item in question. I never got the chance to put forth the WHY clause to my inquiry. He snatched the Italian menu from me with a look of abject horror on his face, raced back with an English menu and left me to sit for another fifteen minutes before returning. I did my best to order in Italian, which won me a new friend for the night. The rest of the evening he doted on me, making sure everything was ok, being more solicitous than he was with his other customers. With dessert, a glass of grappa materialized on my table, but not on the bill. If you've not had grappa before, it's the distilled product of the fermented pressings of the leftover grape pulp from making wine. It's somewhere around 35-60% alcohol, and the good stuff is kinda like good vodka - it goes down smooth with little aftertaste, and has a distinctive but not unpleasant odor. Cheap grappa smells like industrial floor wax remover. This was GOOD grappa - very smooth, pleasant-smelling for grappa.
My point is that by attempting to speak Italian, no matter how fragmented, you'll earn HUGE brownie points, and the locals will go out of their way to take care of you.
On another note, I can pass along a restaurant recommendation - Il Latini (The Lantern), on Via Deli Palchetti 6R. It's in the basement, and a fantastic restaurant. Go early because you'll probably have to stand in line while you wait to get seated. If the weather is cold, the staff will emerge periodically with fresh slices of Parmesan or Asiago and cups of wine to keep you warm. You'll get seated wherever they can fit you in, with who knows who else at your table. Terrific camraderie - I ended up sitting with some Swiss, Italian and Japanese folks who did their best to include the lone American in their conversation. The restaurant is famous for their grilled meats - you can't go wrong with any of it, but if you want the Florentine Steak, come hungry - I haven't seen that much beef on a plate outside of Buenos Aires.