Florence to Montepulciano stop?

San Gimignano.
Chianti hills.

Monteriggioni for a completely walled hill town.
Perugia (might be a bit out of the way) but it is a college town for your son to admire. Perhaps college in Italy?

Thanks, Roberto. Any advice on route? Google maps is showing two: A1/35 is the fastest. Raccordo Autostradale Firenze - Siena is a bit longer. Assuming the former would be best for Chianti hill towns?

I suggest you amble down SR222 through Greve, then take SP2bis over to Radda. Either place would provide you with lunch options. La Cantina in Greve is great! It has some of the best pizza I've ever had. That would be a big hit with your son. Greve has plenty of free parking and a small central piazza with stores to explore.

Radda is a lovely walled town. It is ZTL, but parking surrounds the wall. You can walk from one end of town to the other in 15 minutes. There's good places to eat there as well.

From Radda, there are a number of gorgeous back roads leading to Montepulciano. If you have a later model Garmin, I highly recommend you buy the Italy/Greece SD card and take it with you. The maps are accurate and helpful. We used our trip as an excuse to upgrade to a new Nuvi from our ancient Garmin.

Any advice on route? Google maps is showing two: A1/35 is the fastest. Raccordo Autostradale Firenze - Siena is a bit longer. Assuming the former would be best for Chianti hill towns?

Raccordo Autostradale Firenze is a divided highway and will get you there faster, but the drive will be boring and you'll miss all the charm of the region. The A1/E35 is the freeway. You can drive interstate at home. The drive from Greve through Radda is only 1 3/4 hours. From Florence to Greve adds another hour. That should give you plenty of time to see the countryside.

Since you're staying near Montepulciano, I highly recommend visiting the Abbazia di Monte Oliveto Maggiore (http://www.monteolivetomaggiore.it/lang1/). This is a lovely monastery with a gorgeous sanctuary. Plan to get there about 3:00 and visit the grounds. Then walk up to the restaurant and have dinner. Return to the abbey @6:00 for 6:15 vespers in Gregorian Chant. It's a beautiful ceremony.

The A1 is faster and shorter, but are you in a hurry?
In your shoes, I would actually drive to the Chianti through the Chianti Road (via Chiantigiana-SR222). Once in Castellina, I'd take the Strada di Castagnoli down to Poggibonsi and I'd go to San Gimignano. Then you may not have much time left but go to your agriturismo. On the way there is also Monteriggioni and Colle Val D'Elsa, but if you head to Volterra during your stay in Montepulciano, you have to pass near both on your way there, so you can visit them then.

Thanks, all! Absolutely not in a hurry just looking for a scenic drive with some possible interesting stops. I love all your suggestions. We plan to see San Gimignano on one of the five days we have in the country, so it looks like meandering through the Chianti hills would be a wonderful afternoon drive. And we can still have time for a dip in the pool before dinner!

San Gimignano (and also Volterra) are not too close to Montepulciano (almost 2 hours each way), that's why I suggested to mark that one off your to do list on the way there.

From Montepulciano you are closer to many other destinations, such as:
Pienza, Monticchiello, Montalcino, Buonconvento, San Quirico, Crete Senesi, Lucignano, Cortona, Castiglion del Lago, Arezzo, and even some famous towns in Umbria (like Assisi) .
Volterra is also far, but when you go it would be a good idea to also stop to Monteriggioni on the way there or back.

You are going to have an absolutely wonderful trip!

BTW, the first time I was in Italy was when I was 15 years old, back in 1966. It was on a high school trip to Europe. Our chaperone was a high school science teacher and she made our group of 8 do research on everywhere we were going. I suggest your son studies up before the trip as well.

This will be an experience he'll always remember. It was memorable for me not only because of the wonderful experience, but also because there was this cute girl who was part of the group. We shared our first kiss in Florence and a year ago we went back to Florence celebrate the 50th anniversary of that first kiss!

We also recommend the beautiful Chianti Hills through Greve. Before the turn to Radda (also wonderful), there is the town of Panzano. How about lunch at the famous butcher shop of Dario Cecchini? Look up Antica Macelleria Cecchini. We had a burger lunch, Italian style, which was out of this world. In Tuscany people like their meat.

If you want to drive some Chianti Hills but not take too much time you could continue south on SR222 through Castellina and Fonterutoli to where it meets the freeway near Siena.

One additional note--the "highways" through the Chianti Hills are quite winding and narrow. They are more like a county road than a state highway. It is absolutely a gorgeous drive with many, many small towns and marvelous vistas of forested hills with vineyards and olive groves in the valleys.

Thank you, all, again!

Roberto, I see your point once I looked at the map more carefully. It looks like we will see the best of both with your suggestion.

DougMac, thanks for the great story and congratulations!

Karen and Vic, that's a great suggestion...I would love to see the home of the "Dante-quoting Butcher." And my son would be all about the burger!

Best,

Karen