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Florence & Tuscany Road Trip

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I am so excited for my Italy vacation in early October. My husband and I are flying into Florence, we will be there for 3 days, we are then renting a car and driving to Montepulciano for 3 days, then back up to Greve for 2 days, and back to Florence before heading home.
I am looking for the best scenic route from Florence to Montepulciano with a stop or 2 along the way. Same for the trip back from Montepulciano to Greve.

We are planning to explore areas around Greve and Montelpulciano while we are staying there but looking for some stops along the way.

Thanks!

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The Chiantigiana (SR 222 on the map) is the scenic drive thru Chianti and is where Greve is located. I'd allow at least half a day for that - lots of little villages to explore along the way.
The SR 2 south of Siena is quite pretty with several pullouts offering sweeping panoramas of the Val d'Orcia - lots of photo ops. The Capella Vitaleta is one such spot. You can park nearby and walk to the chapel, set on a hill in the middle of the countryside.
A little off the beaten path but worth the diversion is the Abbazia di Oliveti Maggiore - a peaceful and picturesque monastery compound dating back to the 13th century. The little back roads between there and Montepulciano are all worth exploring - it's just a very pretty rural area. While driving it we stumbled upon a cute little restaurant in the village of Montisi and had lunch there - probably the best meal we had during our 3 week trip back in '19.

For off-the-beaten-path excursions by car I recommend grabbing a copy of "Back Roads Northern Italy" by DK publishing. As the name implies it's full of suggested driving itineraries and secondary attractions that you won't find in other guidebooks. We wore ours out on our own trip a few years ago. Can usually find used copies on Amazon for just a few dollars.

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