Itinerary for Tuscany day-trip

I think that's very doable. Total driving time (without stops) is probably 3 hours or less.

There are some other worthy stops on or near your route: Bagno Vignoni, Castiglione d'Orcia, and the abbey of Sant'Antimo. If time allows, consider additional stops, or at least read about those places and see if they interest you.

Enjoy!

Yes you could.

The drive isn't that long overall, however you'll have little time for each place.

From Monte San Savino to Montepulciano (your first segment) is the longest segment (about 40 min drive). Then all others are 20 min after each other. You could even add Buonconvento, which is pretty and a short detour on your way back from Montalcino to Monte San Savino.

So altogether let's say less than 3 hour drive. In a 12 hour period from 9am to 9pm, subtract 3 hours for drive and park. You are left with 9 hours for visiting 4 or 5 villages (Montepulciano is a bit bigger, but otherwise they are all tiny). 2 hours for each is about right. Lunch in Pienza is about right (visit Montepulciano first from 9:30 to Noon, then drive 20 min to Pienza). Dinner in the last village (Buonconvento?). From either Buonconvento or Montalcino is at least one hour drive back to Monte San Savino, especially if you drive at night (lots of curves).

If you'd like to drive on this famous Tuscan picture spot, it's between Monticchiello and Chianciano. Basically from Montepulciano, on the way to Pienza, turn left toward Monticchiello. After Monticchiello you turn left toward Chianciano and there it is.

Thank you Roberto and Lane...that is exactly the kind of info I was looking for! Most helpful. Any recommendations of restaurants in Pienza or Montalcino?

I had a really nice lunch in Pienza, but I don't remember the name of the restaurant. (I found a photo of me eating there, but no menu or signage to indicate the name of the place.)

You know Pienza is famous for cheese, so if you like cheese, you can always buy some from a cheese shop in town, find some good bread from a bakery, pick up a bottle of wine (I hear they have great wines in Tuscany!!!) and make a picnic.

You know, I had pictured us doing exactly that at some point during this trip...maybe that will be the perfect day to do so. Great idea!

A few years ago we had a nice lunch in Pienza at Trattoria La Chiocciola, near the public parking for the old town. And the next day we had a memorable lunch at Buca Belle Fate on one of the pedestrian streets inside the old town. There are beautiful vaulted ceilings and a menu only in Italian, but the servers were friendly and helpful. Still recall the cart of beautiful, fresh, house made pastries!

I can already tell we're going to be eating and drinking our way through Tuscany! :) Thanks for all the great suggestions.