Best Base in Tuscany

Have you considered staying in an agriturismo (farm)? Virtually every farm south of Florence has apartments and rooms as a secondary source of income.

We stayed between Certaldo and San Gimignano, and found that area NW of Pogginbonsi a great place to do day trips from.

It depends on which places you want to visit. Decide the towns you want to visit, then find something central to those towns. My only recommendation is to stay in a place (hotel, villa, agriturismo) that is fairly close to a freeway entrance, for example the freeway between Florence and Siena. Regular highways in Tuscany tend to be very curvy and go through lots of built up areas, so you won't be able to drive faster than 40-50 km/h (25-30 mph).

We have done this 3 times for a week or two each time. I recommend a hill town small enough to be easy to drive in and out and large enough to have nice restaurants. You don't want to be driving from a farmhouse somewhere into town for dinner as the DUI laws in Italy are much stricter than in the US. You just can't drink if you drive.

Our favorite has been Montepulciano which is a stunning town. We get a place with parking on the edge of the historic center and the area is full of wonderful abbeys, hill towns, and gardens to visit for day trips and on the days you choose to stick at home base, the town is lovely with stunning views onto the Val d'Orcia and Val d'Chiana.

We also once stayed within an easy walk of Lucignano which was lovely and in a hamlet outside Siena which was too small to have a restaurant or even much in the way of a grocery stop.

The Alta Val d'Elsa, or Upper Elsa Valley (Colle Val D'Elsa, Momteriggioni. Poggibonsi, Barberino VE, Certaldo) is the most central and with easy access to the freeway.

An agriturismo or villa in the countryside is a good choice. I wouldn't worry too much about drinking and driving as long as you don't abuse alcohol. Police stops are rare and even more rarely they check alcohol level. They do that only on Saturday nights to kids who might be driving from the disco, since the newer generations have started to abuse alcohol

icroglia,
This may help http://www.slowtrav.com/italy/tuscany/hs_planning.htm

I appreciate all the replies and hope I will continue to get ideas, as thoughts are so diverse, and it really is a hard decision to make. I can say that we prefer to stay in a town big enough to have a variety of restaurants mostly, and perhaps a few shops. Therefore, for this trip, I don't think an agro or other rural location would be of interest. I'd like to visit one and perhaps have lunch, but we prefer more to do regarding an apartment location.

Also, I have read that Montepulciano and Cortona are distant from the highway. Any thoughts about that as both are suggested as good bases.

Again thank you and please continue to share!

I like the country roads near both Cortona and Montepulciano. Check out google street views to get a look at the road character in various areas you're interested in. I'll be driving all through that area in Sept and was there last Spring. Police do randomly make you pull over and check documents.

As I mentioned earlier, first you need to decide what you want to visit. If for example you want to see San Gimignano, Certaldo, Monteriggioni, Volterra and the Chianti Hills, then Cortona is not a good base at all, because it's distant. In that case you may want to stay in or near Colle Val D'Elsa which is central and near the freeway

But if you just want to visit the area around the Val d'Orcia (San Quirico, Buonconvento, Pienza, Montalcino, etc.) Montepulciano is a good choice.

Cortona is a good base for Cortona, Arezzo, Anghiari, parts of Umbria (Castiglion del Lago, Assisi, Perugia, Spello) and is not too far from Montepulciano either.

I'm assuming you will rent a car.

Yes, that is exactly what I think. So, we will spend 5 days in Sienna, and from there we'll visit San Gimignano, Volterra and the Chianti Hills. I think we'd like to see, as you suggested, Cortona, Arezzo, Anghiari, parts of Umbria (Castiglion del Lago, Assisi, Perugia, Spello) Montepulciano. I think we can also include Montalcino and Pieza, perhaps. So we're trying to decide between Cortona and Arezzo as a base. There are pros and cons to each. Cortona sounds touristy but wonderful. Arezzo sounds like it has few tourists(which appeals to me), but has a thriving local community, museums and churches. Any thoughts to help us decide would be really appreciated. All the replies have been tremendously helpful and I thank you so much for taking the time!

I have spent several days in Cortona and Arezzo, and prefer Arezzo by far regarding more options for restaurants, strolling around, local sights. If you go to Arezzo, Sansepolcro is very nearby.

Arezzo is a city, albeit not very large. Cortona is a smaller hill town. So it depends on your personal preference if you want a more city like environ or a smaller town.
In terms of logistics, Cortona is closer to both Umbria and Montepulciano (but not by much since Cortona and Arezzo are only 20-30 min apart).
Cortona has a large number of American tourists (thanks to the University of Georgia and thanks to the novel "Under the Tuscan Sun"). But I noticed the other day when I was there that the higher you go toward the top of Cortona, the fewer Americans you see (only Europeans). My wife thinks that American obesity prevents them from walking uphill too long. Visiting Cortona certainly requires people to be fit. Arezzo has few American tourists, but Europeans are there. However Arezzo is bigger so it doesn't appear as overrun by tourists like the main Piazza of Cortona. However that could change if Americans find out that Arezzo is flatter (although not totally since the Duomo is on top of a hill).
Either place be aware that there are traffic restrictions in the historical center of both places, therefore choose your accommodations judiciously if you want to drive to your hotel and park your car in the hotel premises.

On our last trip in 2013, we stayed in Montepulciano. Wonderful town, great people, food, wine, charm. From there we did day trips. One day we did Pienza and Montalcino. Easy travel. Beautiful countryside roads. Another day Cortona. We didn't want to travel for more than 1-1 1/2 hours each way. Even though we enjoyed the country drives, we wanted to spend more time in the towns. We found Montepulciano was a good place for a base for that reason. Other trips from there could Orvieto. We stayed in the historical center on the top of the hill. Some of the hotels have their own private parking, and there is some public parking available too.

Siena and surroundings is a good base for your intended day trips.

However be aware that Siena has severe traffic restrictions (ZTL) in the historical center, therefore you need to choose your accommodations carefully as not all hotels are accessible by car and/or have parking facilities. There are hotels near the city center which are walking distance from the historical center, but are located outside the ZTL, therefore are accessible by car.
Try this one: http://www.hotelmodernosiena.it/photogallery/

I agree with the above suggestion that you figure out the towns you want to visit and then pick a base. But we found it very easy to drive everywhere and we ended up all over the place! We based near Montepulciano in a small B&B that we LOVED called L'Orta di Panza - our family of 4 had a lovely two bedroom apartment and the hosts are so delightful - it was like heaven. We picked up a rental car in Rome, then went to Civita on our way to the B&B. From our home base, we went to Montelcino, Volterra, and Sienna. We spent lots of time in each town (though there is never enough time), doing a big lunch somewhere and then a simple dinner by the pool at our B&B. We will definitely go back!

I'm so very appreciative of all of this terrific information and suggestions!

Linda

We stayed in Castellina in Chianti last time we were there. Almost halfway between Florence and Sienna, this was a great location to see the sites from. We had a car and drove to Pisa as well, the trip was not that terrible to make.

If you will have already stayed in Sienna I would assume that you will see Florence too. Personally, in our trips to Italy, we like to mix it up: stay a few days in Venice (or Florence) without a car, then rent a car and drive to southern Tuscany and spend a week in an agriturismo. From there, we drive to the many super small hill towns that no one ever talks about. Consider staying at Cretaiole. It is near Pienza which itself is a wonderful town to explore. The roads are great. Besides, who wants to drive through Italy on a major highway? That's one of the reasons we're on vacation - to get away from that! If you are lucky enough to book a week with Isabella in Cretaiole, she will help you create a daily schedule that fits everything you might want to do. I know everyone is different, but for me, that is a perfect Italian vacation.

Lucca = North
Siena = Central
I would go south this time - Montepulciano / Pienza / Montalcino

I have looked at the online book contents, and I do not see Arezzo in Rick Steve's Tuscany Guide. Does someone know if Arezzo is included or not? I also saw the book in a bookstore, but at that time, I didn't know we were interested in Arezzo so didn't notice.

Thanks for all these very amazing suggestions and personal experiences! So helpful!!