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Driving to towns in the Tuscany area

My husband and I will be spending the first week in November visiting towns in Tuscany. We will check in to our villa in Panzano in Chianti on Saturday. I would love some logistical help from those on the forum who have driven in the region. From our base in Panzano, we would like to visit the following: Assisi, Cortona, Montepulciano, Pienza, Montalcino, and Sienna (not in any particular order). On Tuesday of that week, we will need to be back at our villa by 3 pm as we have a cooking class planned.
I look forward to any advice!

Posted by
2182 posts

Panzano will be a great base. We stayed just a few minutes up the road, 5 minutes from Greve.

Every place you listed is doable as a day trip, with Assisi as the furthest away at 2 1/2 hours. I suggest an early start. You might consider leaving that day flexible, traveling to Assisi first. If you have time, you could catch Cortona on the way home, even staying during the evening and catching dinner there.

I have two suggestions for you. Do the winery tour and food tasting at Castello di Verrazzano . The food is wonderful. Be aware this will be your main meal of the day! Also, be aware you'll need to devote at least three hours to the tour and lunch.

Also visit the Abbey of Monte Oliveto Maggiore . We visited there mid-afternoon, then went and had dinner, returning for Vespers, which are celebrated in Gregorian chant. There were the monks, one lady from a nearby village and us. The monks invited us to sit with them and even gave us materials (in Latin) to follow along. We were encouraged to participate in the responses. We are Episcopalian and our younger son is Catholic, so this was a very moving service for us.

If you've not been before, you're in for a treat. You are going in a good time of the year. We were there mid-December and it was delightful. Driving is easy and all the ZTLs are well marked. The rule of thumb is that if it is a walled hill town like Siena and Montepulciano, assume anywhere within the wall is ZTL.

Posted by
11506 posts

You will be near Siena and the other Chianti towns( Greve, Castellina,Radda
and others which all deserves visits.
Assisi is a lovely city but it is in Umbria, beyond Cortona. Why not explore closer towns?
Montepulciano, Montalcino and Pienza can be one day trip.
Look at Volterra and San Gimignano too.
We spent a week in Panzano, and have also stayed in Castellina several times. The road connecting them is SR 222, the historic road. Many visitors travel to Chianti to drive on this road.
Be flexible and decide each morning where you might want to go.

Posted by
85 posts

Suki, yes I know Assisi is in Umbria beyond Cortona, but I feel compelled to see the Basilica of St. Francis. That is my struggle in planning our daily drives around the countryside of Tuscany. All the towns you mentioned I want to see, and I know I can't do it all in one week. We need to take our time and savor every experience and I certainly don't want to rush around!! Maybe I just need to keep going back to Italy . . . not mention all the other European destinations on my bucket list! Thanks for your insight.

Posted by
11506 posts

We keep returning to Italy, tenth trip this year so I understand your dilemma . So, yes, go to Assisi, it is very special, and Cortona on one day trip. In the hillside of Cortona there is the The Celle of St. Francis which you should visit too. We spent a week in Cortona once and it made us want to stay in nearby Umbria which we have since done. Loved it and our base of Spello.