Looking for a base in Tuscany. Or is it two?

We used Montepulciano and San Quirico as bases for our two trips and liked both, two weeks in both places. We stayed just outside Montepulciano which is our usual choice, out in the countryside. However we decided to stay in the old town in San Quirico, our first time in a town. We liked that as well, kind of neat to open the 2nd floor window and look down main street and see what is going on, is the bakery open etc.

Changing bases is time consuming. Checking in and out of farmhouses is even more time consuming than hotels, because you have to be instructed on how everything works at each facility.
If by 5 days you mean 5 nights, that means only 4 full days, therefore your stay is too short for splitting into two separate locations.

You are also extremely optimistic on the places you want to visit. Tuscany is bigger than you imagine and 99% of the highways are tortuous and go through many villages and will not permit average speeds above 50km/h (30 mph). Exceeding the speed limit in Italy has expensive consequences, even if you never see a cop around. Hidden speed cameras are everywhere. The places you mentioned are on opposite sides of the region.

The best one base is as close as possible to Siena and its freeways. That would put you within 90 min drive of every location of interest in Tuscany, except for maybe Lucca, which might require a bit more if you hit traffic on the A11.

I agree with the other post - Montepulciano is a perfect location to explore Tuscany. Florence is only about 1.5 hours, Cortona is about 40 minutes, Assissi and Perugia are also about 40 minutes, and The coast is about 1.5 hours. Everything is accessible including fantastic wineries.

Travelling by car is easy to do in Tuscany. Be sure to go to your local AAA and get an international drivers license for $20. Chances are you will never need it, but you need it to drive in Italy. Just remember this for parking - white lines are free parking, blue lines you have to pay to park (there is a machine always close by), and yellow lines are magic because your car will disappear and so will your money to get it back!

For your stay, check out Fonte Martino (www.fontemartino.com). It's a B&B we discovered last year and have been there twice and are planning our 3rd visit. You can walk to Montepulciano in about 30 minutes through vineyards and olive groves or drive there in 5 minutes.

If you happen to want to stay in town, another of ou favorites is Charming Homes (www.charminghomemontepulciano.com. These are great apartments in town.

Either way, you will have a wonderful time!

Thanks for your suggestions!

Roberto (Is that your real name? If so, it's pretty awesome), we will have 4 full days and two half days on either side as we travel to and from Tuscany. Our itinerary in Tuscany is far from decided and I will keep your comments about Tuscany driving in mind. I am just using the times that google maps gives me to help me plan. As an American, I am used to spending lots of time in the car, but you are right, I want to make sure that we have time to stop and enjoy whatever we see along the way. Also, I am considering taking Florence out of the mix, although that would be sacrilege to a lot of people.

Fonte Martino looks amazing, but regrettably a little out of our price range. The Tuscany section of our trip is only 5 days out of 16, so I am trying to keep the nightly lodging cost at around $125USD or lower if possible. I will look at other places near Montepulciano and San Quirico. I am also looking at places near Montalcino, Monteriggioni and San Gimignano.

Thanks again!