Only one place Tuscany/Umbria to to spend 3 nights

Perugia. If you get too small, you're stuck and bored to tears at the end of the first day. If you want to see something a bit different, make the Orvieto - Todi - Spoleto loop instead of chasing around crowed Tuscany with everybody else.

I like Cortona and Ovieto -- both small hill towns, just for the purpose of staying and relaxing.

It would depend on how much of Tuscany you want to see. Tuscany/Umbria says Cortona, Perugia or Assisi to me. But then, it's a slightly longer journey to Montepulciano, Siena, San G and other great Tuscan sites. If Italian pottery is high on your list, Deruta is a very short trip south of Perugia.

Get the RS Florence/Tuscany book and read about his top choices and why. If this is your first time to the area, I'd recommend Siena.

Thanks all for the suggestions. I'm not planning on traveling to any other towns besides the one I pick to stay in for this trip. After reading the guidebooks and getting suggestions, I think Montepulciano is the front-runner.

I'd still appreciate people's personal favorite and more suggestions.

Thanks again!

Umbria: Orvieto
More stuff to see than most Hill Towns in Umbria.

Tucany: Siena
More stuff to see than most Hill Towns in Tuscany.

My choice if staying put would be Siena -- it's bigger, but once in the central core, it has a very neighborhood feeling. (Best central squar, best evening passiagata, etc.)

We also stayed in Montepulciano (although it was the first half of October, so don't know if it's representative), but we thought it was quite small and sleepy. Fortunately we had a car, so visited the surrounding villages as well. Though don't get me wrong -- we loved the town and it was very picturesque.

Siena - it's quaint, even sleepy if you want (!), got lots to do if you want, transportation (train or bus) if you really want to go on a daytrip, not what I'd call boring LOL! I could easily spend a month getting to know the town. Perhaps one day...

I don't see if your transportation is train or car - make sure you can get to the town you choose :-(

You're not going to go wrong with any of the suggestions. You'll love Montepulciano. You would also love Orvieto, Siena, etc. Have a wonderful time in MP. (We'll be going there in May.)