Where to stay in Tuscany?

Soriano nel Cimino is just a short commute from Rome. If you're wanting to stay south, I'd suggest staying in the very popular Orvieto. The train station is a 70 minute ride from Rome, and Hertz' office is just across the street. You can easily tour other hilltowns from there, and Siena is about 90 minutes northwest.
If you're wanting to stay in the Tuscan hillside, I'd suggest staying in an agriturismo outside of Siena or San Gimignano. It's very easy to make day trips to other great hilltowns including Certaldo, San Gimignano and Volterra.

The post card landscapes are mostly all in the area nearest to San Quirico and/or between San Quirico and Pienza
You can stay there but most choose in nearby Pienza, Montalcino or Montepulciano since they are larger

Hi

I would highly recommend Montepulciano as a picturesque town to stay for two nights. Beautiful views , good restaurants and some wonderful wine shops and cellars. For fantastic views of Tuscan countryside I recommend staying at Mueble IL Riccio a Rick Steeves favorite.

Enjoy

Mike
DC

You need to say if you will have a car.

I suggest that you think about what "picturesque" means to you. I generally like waking up in a city, especially if it's an old medieval center. But you have to consider the towns (even lovely Cortona) that are very busy during the daytime - and what that means about the perceived level of charm they have for you. Some people ( .... with cars) prefer a rural setting, even though that exchanges culture (like museum art and performance opportunities) for "local food and living." I'm not telling you which is better.

I agree that Soriano nel Cimino isn't a good choice. We loved Orvieto, and it's good for train travel. Someone from, say, California (you haven't put your home city in your Profile ... ), might be annoyed that you have to pay to park outside the walls in Orvieto (and most other places.)

With a car, I would say that there is so much driving to be done in Tuscany, it doesn't matter the location of where you stay-in terms of distance to attractions. Without a car, it makes a big difference. We don't like to change hotels, so we stayed in the same rural luxury hotel for four nights, in Sinalunga.

Check out Relias la Belluccia in Montecatini. Charming, clean, affordable, and safe. We really enjoyed our stay there. The location is great for your plan and the food is very good. The chef will make to order his suggestions or your request.
Lorieann

Does it have to be Tuscany? We stayed in Tivoli just outside Rome. Very nice town and a couple of cool villas to visit (Villa d'Este). Also, Hadrian's Villa is close and a must see if you are out there.

If you desire "postcard" landscapes, you might prefer an agriturismo. You are already staying in towns - Florence and Cortona - so maybe a rural setting would fit the bill.

We loved Cretaiole in the Crete Senses area to visit Montipulciano and Pienza and we adored Borgo Argenina outside of Greve in Chianti. Elena at Borgo cooked with her guests and the heavenly homemade breakfasts eaten in the courtyard overlooking the vineyard was divine - that was a postcard landscape !

I would book a hotel in the historic center of Montepulciano. It is a lovely town with stunning views of the Val d'Orcia from the ramparts as well as the Val d'Chiana. There are a dozen or so nice restaurants, pretty wine bars with views, a lovely town square. Great town and convenient for day tripping in the area. Here are some snapshots in the general area, some of them taken from the walls of Montepulciano:
https://janettravels.wordpress.com/2011/09/20/patterns/
We spent two weeks here in an apartment with a view out over the valley and used it as a base to tour in the area. But on many days we just stayed in town enjoying the views and the wine and the local restaurants.

Thank you Janet for the lovely photos. I am planning to stay in Montelpulciano and this thread is quite helpful

If you are staying in Montepulciano in an apartment: it appears that there are no bakeries in the historic center but this is not so. You will probably need to ask directions as it is not easy to find but there is one hidden away on a side street a bit downhill from the clock tower with the metal figure that strikes the hour. It is easy to walk past even when you are nearby. For groceries, head out the bottom of the town to a supermarket not far from the lower entrance to the historic center. (if in a hotel, then nevermind -- restaurants galore) We particularly liked the Grotte across from the large church outside the wall at the base of the hill.