Best Place to Stay with 3 Days to See Tuscany and Umbria

you will need to rent a car for what you intend to do.

One area to consider is near the Val d'Orcia, southeast of Siena: Pienza, Montepulciano, Montalcino, San Quirico, Buonconvento, etc.

You can't cover all of Tuscany and Umbria from anywhere, since the two regions together are as large as Massachussets and New Hampshire combined, but that area provides some great photo opps.

Some famous towns in Umbria are also only about one hour + drive away from there (Assisi, Spello, Gubbio, Orvieto, Castiglion Del Lago, etc)

Thank you SOOOOO much for the response. We planned on renting a car when we leave Florence. Can you recommend a good car rental company? And, do you think we should reserve the rental in advance?

First of all, I have always heard that renting a car in advance gets you better rates than doing it from Italy. Look at Autoeurope.com and kemwel.com.
A number of years ago, we rented a cottage near Lake Trasimeno. The location was great for visiting many of the towns in Tuscany and Umbria. We were near Chiusi, not a bad town, but not the most picturesque in the region. However, I suggest looking at a map and picking out a base near there, with easy access to the A1 autostrada.

For a great photo op in itself,
Take a look at http://www.borgorapale.it

Located at the top of a hill, in a small village, overlooking a valley, with great hosts and easy access to all the places Roberto mentioned.

It's still our favorite in Tuscany.
Be sure to look at their list of restaurants and the easiest way to access the hill towns.

They do rent by the night if they have availibitly.

Thank you all! Your responses have been VERY helpful!

There are a few tiny hotels in San Donato (close to San g.) and easy in and out to drive around Tuscany and some amazing views from this tiny little town.... Nothing much there, a winery, a church and a few hotels, but it overlooks a vineyard and the tuscan countryside. I am a photographer and everywhere in this little village is a beautiful image.

Thank you SO much for the recommendation! San Donato looks extremely picturesque!

You will love it as a photographer. I found it when I took my grandson to Italy... We stayed at the little B&B Antica Dimora. When we rounded the final curve into San Donato there were about 6 or 7 women with easels and canvases and they were painting the tuscan hillside. My grandson was 9 at the time and very artistic. After checking into our room and opening the shutters he wandered down to where the women were painting. One of them gave him a canvas and his first pallet of paints.... It was like watching a scene unfold in a movie, so of course, I love the place. It is so quiet and peaceful so I feel like it is one of my very own 'back doors.':)

If you go to San Donato, eat at La Toppa.

Don't know if you have left for Italy already or not, but we stayed in Montepulciano 3 nights as a base for the hill towns and really enjoyed the town. However, Assisi is probably one of the most beautiful towns we visited!