Tuscany Suggestions

I suggest reading up on Tuscany and your other destinations and then reading up again. Only you know your preferences - Italy and Tuscany have too many attractions to allow easy answers. Perhaps start with this website's Tuscany section which includes a map to help with the geography. https://www.wanderingitaly.com/maps/tuscany-maps-guide.html
I do especially remember the drive along the SP60 through the Crete Senese hills from San Quirico to Siena, so don't miss that route.

Hello Suesea,

In San Quirico d'Oracia you'll be very close to Pienza, Montalcino and Montepulciano all of which are suitable famous hilltowns and are worth visiting with the second two being particularly famous for wine. San Gimignano is probably close to 2 hours both ways and I'm 100% sure there are more interesting places closer to where you're staying versus making that drive for one particular town. Cortona is closer to an hour each way if you want to visit a Tuscan hilltown famous for being beautiful.

Check for sagras in the area while you are there. These are local celebrations usually for food - eg the mushroom sagra - and those I would love to participate in given the chance. They are often in small towns so it's hard to participate without a car even when you find out they're happening. These are often at different dates and are very local and difficult to plan from the states.
Some examples:
https://orciawinefestival.wordpress.com/
https://www.giraitalia.it/antiquariato_collezionismo/62243_64_edizione_mostra_mercato_dell_artiginato.html

The classic Heart of Tuscany drive Rick recommends (which I've done) runs past Lake Bolsena and up SR2 into Tuscany. I've done it from Orvieto but if you're coming from Rome (which I haven't done) I'd look to take the SR2 north out of Rome or maybe the SS3 heading north and then head back to towards Lake Bolsena. I can't say which is more scenic but I know SR2 heads through a couple of towns including Viterbo which may be worth a stop to check out the old city center if you're looking to break up the drive.

Heading north I would keep onto SR2 past Siena (always worth a visit) or you could then throw in San Gimignano as a detour but I would then add Volterra (or just do Volterra instead) if you're looking to explore on this drive rather than just get there. But the drive itself staying rural I would count on 4+ hours of driving alone.

In all of Italy but in Tuscany especially don't forget to slow down and enjoy the quiet la dolce far niente in thay amazing place.

Hope that helps, sounds like a great trip,
=Tod

We did Rick‘s suggested drive from Montepulciano to San Filippo hot springs to bagno Vignoni hot springs to Penza. It’s in the books and a really fun day!

Thank you! Your comments are very helpful to help us in our planning!