Where To Stay In Tuscany

In my opinion, the very best base is Tuscany's "capital city" of Florence. I have lived there among other European cities and can never get enough of it. You might not even want to leave the city to see anything else- it is that good. In fact, you don't even need a car in Florence as the public transport and train system is so excellent and you can stay in a central location. If you do venture out from the city to see other areas of Tuscany, I would recommend seeing Siena, Pisa, and Lucca at least. Again, you can save on car rentals and just take the trains and use public transport in those areas. Public transport in Europe is a million times better and safer than in the USA and this is how Europeans get around in their day to day lives.

As for where to stay, we usually choose the Bernini Palace in Florence for its elegance and comfort (and free wifi too!) which, if you skip the car rentals, petrol, etc, might be in your range ($239 in March when I often celebrate my birthday in Florence). It is also a few minutes walk (1 or 2) to the Uffizi Gallery and the Piazza della Signoria and up to 5 minutes walk from Boboli Gardens and a bunch of places to sightsee. http://hotelbernini.duetorrihotels.com/en The staff is friendly and can't do enough for you.

If you want something cheaper, the Villa Olma Firenze-MGallery Collection is a good place. It is around $90-$110 in March.

Take the train to Orvieto and pick up your car there. Two places we love...

http://www.borgorapale.it/ on the Tuscan Umbrian border

http://www.collelungo.com/EN/index.html in the heart of Tuscany

Towns - Small or large. The towns mentioned are very, very good. Small towns would include Volterra, Panzano, Monteriggioni, Certaldo, Montecattini Terme, Montecattini Alto, San Gemini (Umbria), and Montefalco (Umbria). But, just about any spot on the map will give you an Italian experience. Enjoy it.

We also flew into and out of Rome when we last visited Tuscany since flights were much less expensive. After landing in Rome we immediately caught a train to Florence where we spent 3 nights. From Florence we were able to take a day trip to Lucca and Pisa. Florence is a wonderful city but you do not need or want a car in Florence.
We rented a car upon leaving Florence at the San Sovino Hertz location. It is very easy to reach by tram and outside the ZTL. From there we drove to Montepulciano. Montepulciano was an ideal location as it allowed us to make several day trips. We stayed at the Albergo Duomo which provided parking.
Returning to Rome, we dropped the car in Orvieto and then continued by train.Have a wonderful trip.

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

If you have a car, logistically the best base for day trips is anywhere along the freeway from Siena to Florence. Colle Val D'Elsa, Monteriggioni or Poggibonsi area work perfectly. Just do a google map search for hotels in that area. Many are converted country villas just outside of town.

We stayed at an agriturismo outside of Pienza (from the RS book) and thought it was a great base for the Tuscany region (we did Florence separately -- to me, those are two completely different experiences). We were able to get to Montalcino, Montepulciano, Cortona, Siena quite easily and then also hit some towns on our way from Florence and then as we were making our way to Rome. We found that getting/dropping cars in the cities was actually cheaper than the hill towns, but I'd check out both. If you're flying in to Rome, I'd check the airport pricing and then Orvieto is probably the first major hill town stop that would have a rental car (or Siena would if you want to go up that far).

Stay in Florence for one week and go and visit Sienna and San Gimignano and eventually Lucca. Easy and frequent bus and train connections

Our 2nd trip in 2012, we stayed at Agriturismo Cioccoleta Orvieto just 3 miles or so out of Orvieto. In fact, while there, you're looking across the rolling hills at Orvieto in all its glory. When you arrive at Orvieto by train, cross the front parking area, then a street, and Hertz is just across the way. Rent a car to get to the agriturismo, and take the opportunity to visit other areas nearby, such as Civita di Bagnoregio like we did. When visiting Orvieto, there's a nice parking garage with escalator or elevator on the north side of town. Or park near the stazione and take the funicular. We parked north of town and just took our time.

Spring 2014 we based in Firenze for a week and just took rail and bus to various places for day trips, like Lucca, Siena, for example. We also toured with Rick Steves buddy Roberto Becchi into Montalcino and Torrenieri, etc, all day. And of course visited sites we hadn't visited in Firenze on previous trips.

Then we stayed a week in Cortona. We ventured out into the Val D'orcia, Montisi, sites where Gladiator and English Patient were filmed, Pienza with our friend Luca Garrapa who runs Hills and Roads car or van tours out of Siena. I didn't do this but was ready to- take a train to Chiusi just SE of Montepulciano. Cross and go up the street a little from the stazione to Hertz and you're now free to visit Pienza, Montepulciano, Montalcino, all over southern Tuscany, stay at any of the many agriturismos, and then return the car to Chiusi and hop the train to wherever. My next trip will include this so we can stay at Sant'Anna in Camprena where English Patient was filmed (90 euro night, and 20-25 euro per person for dinner with wine), and home base there a few days, and then stay with our friends in Cortona.

I try to avoid having to drive in Italy but in rural areas of Umbria and Tuscany it's no problem. Just get the super cover insurance supplement to get the deductible down to ZERO. Otherwise, any damage will still incur a significant chunk of change.