I lived in Italy for three months, and it’s fabulous. You can’t go wrong there 🙂 You absolutely do not need to know how to speak Italian, but like any other place, a little bit of effort is always much appreciated by the locals and they’ll treat you well. Pick up a pocket phrase book to take with you.
If you’re planning on traveling around Italy at all, the train stations are overwhelming and not the easiest place to get around if you don’t speak Italian (ie. if you need to book an overnight train), so this is where you’ll want the phrase book for! A lot of restaurants have Italian/English menus and in any case, the food is amazing, you’ll be fine with whatever you order. As a general rule, I avoided restaurants that had english menus because they were a bit touristy and I like more local/authentic restaurants without the tourbus turnover.
I’d highly recommend Florence, it’s romantic, beautiful, the people are wonderful, amazing shopping, great restaurants, totally safe. Rome is good, but not my favourite, I haven’t had a great meal any of the times I’ve been there. It’s worth going for the history and culture, but I wouldn’t want to stay there for two weeks personally. Pisa is a one hour train ride from Florence and I really enjoyed it, it’s a really sweet little town. You could go to the coast and do Cinquo Terre, which is beautiful, but after a few days you could get bored. Sardegna (island off the west coast) is gorgeous, but ridiculously expensive. It’s a great place to watch uber rich people though. Rent a scooter or car, don’t take the taxis (costs a fortune, we found out the hard way!). Venice is beautiful, very romantic. I’ve been twice and enjoyed it, although my heart is with Florence, I have to admit. Sienna is gorgeous too. Really, if you rented a car and spent a few days in each place you couldn’t go wrong! Avoid Naples, it’s very dangerous, even Italians don’t go there.
Other European countries to visit: I love Spain. I found there aren’t as many English speakers there as Italy though, but you could still get by fine with a translation dictionary. Barcelona is gorgeous, Seville is amazing… I’m not a huge fan of Portugal (sorry!). Malta is a fun place, although small, but I spent a month there when I was a teen and enjoyed it. Germany is stunning. I’ve always wanted to go to Sweden but haven’t had a chance, I’ve heard it’s great though. I’ve also heard terrific things about Turkey.
Honestly, if you handed me a plane ticket to anywhere in Europe, I would go back to Florence in a heart beat. If you decide to go, let me know and I can PM you some great restaurant recommendations 🙂