Orvieto, Siena, or Montepulciano?

Personally I would choose Siena. I love the place and it's fairly easy to travel to other towns from, especially Florence. Also large enough to always find ways to fill in your spare time. Down side could be lots of tourists though. The other towns are smaller and this may appeal more to you. I suppose it really depends what you are looking for.

Siena because it's bigger and there's more to do there, if that is a factor for you since you're going to be there for a month. But all 3 places are great.

I'm a younger student so I don't really know whether I would like the ambiance of a small town compared to all the things you can do in Sienna. I wanted to opt away from Rome or Florence (the only places in Italy I have been to) because I really want to learn a lot of Italian and I feel like going to one of those cities I would always have english to fall back on, whereas in smaller towns, most people speak Italian, and not english, and therefore I would be forced to Speak only Italian for all 4 weeks. Do you know if most people DO speak English in Siena? Its a really tough decision because whenever I say the word "Siena" someone will say OMG I LOOVVVVEEEEEEEE Siena, (Just the way that Rick Steves describes it. So its gonna be a tough choice! Thank You, though.

Actually, I think Siena has a large population that lives apart from tourism and so the automatic switching to English could be less likely. That said, English is taught in schools and seen as necessary for a professional career, so in any city in Italy the younger people you meet will likely have English. But I agree with the others; for four weeks I'd want to be in Siena.

Town populations may enter into your decision:Orvieto 20,000Montepulciano 14,000Siena 55,000

I would pick Siena because as others have stated there is more to do there. Siena also have transport connections via bus or train to numerous other towns for day trips.

Sasha ,

Living here is differently than "vacationing" here... and if you want to be immersed in the culture and economy you must consider this. Having said that, I would head to Siena. As Sam says it has excellent bus & rail connections - and it is also larger... and if you're here, in one place for more than 5 days, you will want those options. Where's the supermercado, the park, the farmacia, what other neighborhoods can I see, etc. all are BETTER options if you're in Sienna. And I've stayed on the outskirts of Sienna and is very NON-touristy... just depends on where you get your apt.! Wherever you choose, you are correct - It's ITALY! Have a great time!

Ciao,
Ron

I'm going to shake things up a bit here and suggest leave Tuscany alone and go to Rome if you really want to learn Italian. I found many more people spoke English in these small tourist hot spot towns than they ever do in Rome, and they are usually full of Americans, especially college students. Rome has so many people and so many places where they don't speak English, and I found Romans to be very patient when I was at the beginners stage. Plus in Rome there is so much to do! The most important thing to remember wherever you go study is that to learn the language you must live with someone who does not, the best situation is to live with a family instead of in a dorm or by yourself.