14 day itinerary from Montaione

Jose C

New member
We are staying in a farmhouse in the Montaione area for two weeks in September 2023 and would kindly like your help with suggestions on what to see during our visit. We will have a rental car and are already planning to see Florence, Pisa, Luca, Siena and San Gimignano. We really want to also see some beautiful wineries and drive through beautiful typical Tuscan countryside. Thank you!


The Tuscan Expert ;-)
Staff member
Oh you will already be staying in the heart of gorgeous landscapes with great views of Chianti!! On your way to Florence, Siena and San Gimignano you'll be getting more of the Chianti countryside with vineyards and olive groves, but if you want to get the rolling hills with cypresses you'll need to also add in a drive through the Val d'Orcia. Head to Siena, then on to Montalcino and to San Quirico d'Orcia, Pienza and Montepulciano. You'll get the landscapes you see in postcards from the region there.
If you also take the back road to Pisa and skip the FI-Pi-Li you'll get more gorgeous views, but also the faster road cuts through valleys that have views of hilltop towns off the road as you drive there.

As for wineries, they are all over the place. Are you interested in particularly beautiful locations or architecturally modern? There are small boutique wineries across the region, I would highly recommend you look into these three I've highlighted in a recent blog post:
Dianella is closest to Montaione but if you're going to Greve, I highly recommend Viticcio.
As for modern, everyone will tell you to go see Antinori and that isn't far from Montaione, it is a gorgeous place. If you love them, I'd suggest to go to Badia di Passignano for the gourmet meal with Antinori wines.