You don't sound naive, you are my hero!

I love Italy and have rented houses in Tuscany and apartments in Rome. I've been to Florence many times, but just for short stays. I'm back in June to finish up my Master's degree at my American University that has a location in Rome. I have children who will accompany, so an apartment is the only way. My pick would be Florence or Rome. Florence is small enough for it to feel special and manageable, but large enough to have a great transportation system, is really beautiful, has great restaurants and a lot to do/see. You could rent a car and drive to numerous charming and beautiful smaller towns whenever you wanted. Rome is a great option too and I do not need to explained why. If you rent an apartment in a neighborhoods where the locals live instead of a tourist area, you will get to know people at the local grocers, cafés and shops. Two years ago at the start of my degree program I rented an apartment in the Parioli neighborhood, adjacent to Villa Borghese and it was wonderful. I left in the morning with everyone leaving for work, stopped at the same coffee shop with them in the morning, waited at the taxi stand with the same people each morning, went to the local bar at night for a glass if wine, and stopped at a market for cheese, ham and wine each night. This little place had wine tastings each evening and I sat down and tasted with folks who lived on my street.

Whatever you decide it will be awesome and you are awesome!

Just a quick vote for Verona. So close to the Lakes, Venice, Florence, Milan -- and all that opera! It's the perfect size, too.

Hi
I am a 55 year old American living in La Coruna Spain. At times I love it and at times I don't.
Did you end up spending 3 months in Italy and if so, where? I speak Italian and think about going there too. The winter is tough in Galicia so southern Italy could be great for the winter months