tuscany

With a car, I'd recommend you not try to stay inside an old city, since driving and parking is really difficult.

A good option might be to find lodging at the edge of town that has parking, so you can walk into town when you want to eat, shop or sightsee, but also it's easy to get in the car and drive for day trips to see other places.

Another option is an agriturismo with kitchenette, giving you the fun of buying food at a local market and preparing some of your own meals while enjoying the feel of being on an Italian farm.

We loved Agriturismo San Gallo, at the edge of Montepulciano, and others will also offer places they stayed and loved also. Not many will have bad experiences to report. Most will have GREAT experiences to report.

My San Gallo review at TripAdvisor.com is HERE.

There's plenty to do in the Pienza/Montepulciano area. I think you'd LOVE spending all 4 days in this area. It's great to unpack once and return to the same place for several nights, vs. packing up and moving once or twice.

From this area you have GREAT places to choose from: Pienza, Monticchiello, Montalcino, Siena, Montepulciano, Cortona, or lots of other possibilities. This area is Val d’Orcia, the very heart of Tuscany. You cannot beat it!

Your friends have given you good advice on Pienza. It's a great place and I love the size. Small enough to easily park at the edge and walk into, but big enough to have several places to eat and shop, and lots of history. Do not miss the Piccolomini Palace tour. Very interesting. What the Medicis were to the Florence area, the Piccolominis were, on a somewhat smaller scale, to this area.

joyce,
This will give you some ideas http://www.slowtrav.com/italy/tuscany/hs_planning.htm

I agree with PAtrick. The area around Pienza is one of our favorites! He listed some of the great towns to visit. We always stay just outside a tiny town Celle sul Rigo, near San Casiano de Bagini, both are very picturesque. We stay at Il Poggio, which is lovely. Also you are very close to Umbria and Orveito and Asissi which are also great to visit. Very easy with a car. I love driving in this area.

After leaving Florence I would suggest staying at Casolare di Libbiano , an extremely nice B&B just three miles outside of San Gimignano and also, very close to Siena as well as Volterra. Berta and her husband Andrea are excellent hosts and the property and rooms are wonderful.
Http://www.casolarelibbiano.it

A really central location from where you can see an awful lot of Tuscany from one very nice base of operations.

Ciao, Greg

thank you all for your suggestions. I tried the agriturismo that Patrick suggestred but there were no roooms. That is pretty much what I found everywhere yesterday. Who know that 9 or 10 months in advance so many places would be full. i think it must be that many of them are so small. I will try the other places today. It helps so much to get real names of places and to hear about other towns that are nice to stay in. thank to all ..keep the infor coming...i may not have any luck with these either.

Joyce, another great way to look for lodging is TripAdvisor.com, because you can read reviews of the places from other travelers. Just enter the name of the town you want to stay in, then click the link to show hotels, etc., in that town.

Assume that at least a few of the excellent reviews are by the owner of the place,and at least a few of the bad reviews you might see are from cranks who aren't ever pleased anywhere.

But if you find a place with a dozen or more reviews and the overall score is high, you can feel pretty sure it's a good place to stay.

well, i checked out all of your suggestions and every one of them was unavailable. thanks so much, though. i did find onre called Hotel Residence San Gregorio. i will let you know how it is. At least it is in Pienza, where I am now convinced is the best location. any other info for this area, things to see, places to eat, etc. greatly appreciated!!

"Who know that 9 or 10 months in advance so many places would be full."

This is a surprise. Last year when I made reservations for our trip to Italy a lot of places said I was contacting them too far in advance (I was about 11 months before travel time), and told me to to contact them again six months before our trip. Later, I didn't have any problem getting reservations six months in advance at any of the nine places we stayed!

We traveled in late May/early June 2009, and we reserved 3 rooms or apartments at each of the nine places. We didn't find ANY place that was booked up six months in advance. You're having really bad luck here!