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4 days Southern Tuscany - What towns to group in each day

Hello,

We will be arriving by car in Pienza as our home base for 4 days. We are interested in seeing San Quirico, Pienza, Montalcino, Montepulciano, Montichiello, Voleterra, San Gimignano, Val d'Orcia. We will be stopping in Siena on our way to Florence.

Any advice on how to best break out our days and which towns make sense to see on the same day? We are hoping to have each day be leisurely and not rushed. Appreciate any insight on the best itinerary.

Thanks for the help!

Posted by
913 posts

Only Volterra and San Gimignano are a substantial drive (2 hours or so depending on traffic) away from Pienza. Sounds like one day with a long drive to do both. The other towns are much closer so you have greater flexibility.

Rural roads are twisty and can be fun, but are not necessarily fast.

Posted by
340 posts

I'm planning a similar trip. I find Google Maps to be a tremendous help to plot the most convenient routes.