Which are the best hill towns to visit?

It would really depend on where you are traveling to beyond the stay. Siena is great and close to Florence. Montepulciano is also great. However, since you mentioned Umbria, my suggestion is Assisi. We found it to be quite beautiful with great shops and gelato.

However, as I mentioned above, it depends on where you go next. Assisi, as beautiful as it is, is a bit out of the way. There's extra train travel to and from.

Never been there, but had friends-whose opinion I trust- live in the area for 2 years and said the best place was Trevi (near Spoleto) and the best restaurant ever is L'Ulvio in Trevi.

what a great prob to have. I would discount Pienza and Siena (they are a great visit but I am prioritzing) Montepulciano and San Gimi are a toss up. I haven't visited Volterra yet.

If you can stay the night San Gimignano is wonderful, after the day trippers have left. Siena is not real easy to get in and out of for an overnight. Montepulciano, Pienza and Montalcino (my favorite) all require buses from Siena (or I think Chiusi). Cortona is right off the train line heading to Firenze, you might want to consider it (very pretty, great food, an authentic Tuscan hill town).

I have been to all but Pienza.

If you're a big wine fan, I would go with Montepulciano.

I thought the baptistry and duomo in Siena were among my favorites in Italy. There are probably more things to do in Siena than in the other towns.

Volterra made me feel like I was living in this old city. Not as many sites but great for walking around through neighborhoods and along the wall that circles the city.

San Gimignano had the great towers but it didn't seem like a place I would spend a day and a night in.

If I had to pick a place to go back to it would be Siena.

I vote for Siena - I thought it was just beautiful.

I was trying to get a reservatio for one night in Orvieto and struck out. Watch out, many places have a 3 night minumum.

Stephanie, I found an agriturismo a little north of Orvieto that waas fine with staying one night. It is called Larocca. The website is http://www.laroccaorvieto.com/ We haven't gone yet but it sounds really nice and other people recommended it on this site. Good Luck

Laura
I just returned from all those places yesterday. Orvieto is a great place to start. We stayed at the Ripa Medici which is very nice inexpensive B & B, newly remodeled with a great view. We also love Volterra. We have returned there three times. Any Questions don't hesitate to e-mail. I have some ideas that worked well for us. With opinions on each place.

Another great B&B in Orvieto is the Palazzo Cardinale. Expecting another tiny room, we were pleasantly surprised to see that we had our own small apartment complete with a living room, bathroom, kitchen and loft bedroom. We stayed there 1 night in March and the price was extremely reasonable. Obviously, being in May, the price might be higher but it's worth a look. It was an excellent place in a 500 year old building. Also, while in Orvieto try to see Orvieto's "underground" -- very interesting!

All the places you mentioned are really nice to visit and all have their differences. I like Volterra, its a great walking town. Siena has some great places, too. You could stay just out side of Siena. We stayed at L'Aia Country Holidays. It was a wonderful old farm house. Also Ripa Medici in Oriveto does not require more than a day's stay. Orvieto is another town with great places to eat, wonderful views and beautiful Duomo.