4 nights in Tuscany

Two years ago, we followed your exact itinerary. It was a 30 minute easy drive southwest of Florence.

We stayed between Certaldo and San Gimignano on an agritursimo. Virtually every farm in the area has apartments or rooms as a source of secondary income. It was a great location to do day trips from to Volterra and Siena.

You can find such places on AirBnB.com, Booking.com and many other internet sources--even Craigslist.com.

Go onto GoogleMaps.com choosing a city. If you hit "+++" to magnify the map In the area, icons will pop up showing hotels and B&B's and farm accommodations. Click on the icon and you can get the hotel/B&B's direct website.

The most central place for the most famous Tuscan towns is somewhere near the freeway that connects Florence to Siena. Roughly between Impruneta and Siena. The area near Colle Val D'Elsa would be ideal as that is where you have also the road that takes you to the Chianti or the one that takes you to Volterra. Whatever accommodations you find, in a small town or a countryside villa/farmhouse, check the location on Google Maps and make sure it's sufficiently close to that freeway. Some farmhouses are really isolated and in some roads in the countryside of Tuscany you can't drive over 20 or 25mph since they are narrow and curvy.

We spent a couple nights at this little place near San Gimignano early May '13. Loved it! We're planning to make it our home base again for a week in Tuscany next spring. We did exactly as you plan to; rented a car at Pisa airport, used it throughout Tuscany and Umbria and returned it in Orvieto and continued on to Rome by train. Hertz is literally less than a two minute walk from the train station. I won't go into all that we liked about Il Casalore di Libbiano because I'm including the url of their website, it speaks for itself and it is NOT overstated in this case. Not sure what reasonable is to you but as I recall we paid about 130 euro/night. www.casolarelibbiano.it/

We also spent a couple nights in Orvieto. If you haven't ever been there I would recommend that as a home base as well but not as central as San Gimignano. We stayed at Villa Mercede, run by a religious order, pretty spartan in way of amenities but great room, great view, and great location right next to the duomo with on-site parking within the restricted zone, a huge plus. Paid 70 euro/night. Their website is in Italian but you can click "translate this page" if you search with Google Chrome. And if you do search it be sure to searh Villa Mercede Orvieto. There is another hotel by same name just south of Rome.

Have a great trip!

Try this> http://www.casafrassi.com/?page_id=312&lang=en but book thru Venere.com, prices are less expensive.

Siena->18 miles San Gimignano-> 19 miles Voltera->29 miles Greve in Chianti-> 12 miles

Radda-> 7 miles Montalcino-> 42 miles Pienza->48 miles Note these last two take 1 1/2-2 hours to get to.

Orvieto is 92 miles.

Hotel Sovestro, just outside of San Gimignano, is great for the type of itinerary you have. We have stayed there several times and it is so nice at the end of the day not to have to navigate the small streets of most of the towns to get to your lodging. The hotel is well located, immaculate and very comfortable. They serve a great buffet breakfast which is included in the price of your accommodations and the restaurant just steps away, Da Pode, serves wonderful and authentic Tuscan food.

Thank you everyone for your suggestions. I ended up staying at Casa Frassi in Chianti for 4 nights. It was delightful. Beautiful location, quiet and peaceful. Easy to get to San Germignao, Sienna, and Volterra. Driving was more of a challenge than I expected.

Thanks for reporting back!