recommendations on where to stay in tuscany

have stayed at monasteries in Cortona, and San G, using monasterys.com. they were both inside the cities, however, the one in San G was very austere. Check out their website-price and location were right for us.

Jay,

In October of 2012 four of us stayed at Agriturismo Marciano just outside Sienna. It was fabulous! The best meals I had in Italy were there and they make lovely wines and olive oil. Although I never did it you can walk to Sienna from the place. It was a great place to base out of in Tuscanny. All the best and enjoy the trip!

We stayed between Certaldo and San Gimignano at a farm apartment. Virtually every farm in the area has apartments and rooms as a source of secondary income. The properties go from good to great in quality, and I'm talking hundreds and hundreds of places to stay.

We went to Booking.com and found many accommodations.

You can also sign into Googlemaps.com for the area. Then hit "+++" to magnify the page until all the hotels and B&B's show as little icons. Double click on the icon and you'll usually be able to go directly into the agriturismo's website.

We shopped for groceries @ Poggobonsi, and it was very easy to get to Siena, San Gimignano, Volterra and other great hilltop towns from that area.

In October 2014 we stayed at an Agriturismo near Orvieto called Antica Olivaia hosted by Daniella and Marco.
The room was just right and there was a pool. Our host cooks dinner several nights a week to serve to guests who have paid a fee and made a reservation. The food was excellent and a passion for Marco. Daniella was very helpful in providing directions to various places and she was sweet and accommodating . This olive farm is a bit off the beaten path but provided us with a lovely stay.

I second the suggestion of Agriturismo Marciano. Wonderful breakfast and dinners. Nadia mapped out a road trip through Chianti and on the day we left and she did the same for our journey to Orvieto. We didn't stray from her directions and were rewarded with lovely drives through Tuscany and on the way to Orvieto all on back roads. But they are very popular so book early.

Looks like Jay's trip was last month. While an agritourismo has more limited services/choices you can walk to, there is usually a benefit of being able to park closer to your front door.

It is too late for your post but perhaps others may find this useful. We stayed at Il Canto del Sole, near Sienna. In short, it was a wonderful experience. The innkeeper came to the train station to pick us up and dropped us off and the end of our visit. We arrived late in the afternoon and not having transportation, asked if they could provide dinner - it was a fabulous feast accompanied by wine that they had produced on the agriturismo. The room was clean and very comfortable and the inn had a commanding view of the countryside near Sienna. If you're looking for a beautiful place to stay and have a car or just want to stay in one spot, this is a wonderful place.

Recommend the Villa Fontelunga in Pozzo della Chiana located between Arezzo and Cortona. Wonderful personnel run the establishment with wonderful appointed rooms with private bath/shower, breakfast and lunch served outdoors with a view of Cortona sitting on a mountain top (an awesome site at sunset). Swimming pool included! And by all means do have one of your best ever Italian restaurant experiences by dining at the nearby restaurant Lo Steccheto in Marciano della Chiana. The chef, Giancarlo, will amaze you with his restaurant interiors and the best Italian food we have experienced in our 24 years of visiting all of Italy! (check this out on Trip Advisor).