Stops Along the Way - Orvieto to Bologna

Here are a few to look at.

Cetona, Castiglione del Largo, Cortona, Castiglion Florentino, Anghiari, Arezzo, Montevarchi, Prato, Pistoia.

All but Arezzo are smaller towns or Villages.

Hello Danielle,

I would recommend that rather than take the A1 you go west on SR74 from Orvieto and swing by Lake Bolsena and then head north on the SR2. This route is really the visual tour of Tuscany and takes you through beautiful countryside and past many famous Tuscan towns.
For wine: Montalcino, Montepulciano or Greve in Chianti
For the classic hilltown visit: Siena
Smaller town experience: Pienza, Cetona for smaller town experience
The exit signs off the SR2 read like a series of places you've always heard about. RS calls this region the heart of Tuscany.

Taking this route will add at least an hour to your drive but it is beautiful country and offers a long list of places to visit along the way. Chose a place or two to visit depending on how much time you want to spend on this driving adventure. Investigate a couple of places and follow the signs. Always be aware of parking on the outskirts of town and avoid driving into ZTLs - limited traffic zones - in many cities.

Have a great trip,
=Tod

Here are some wineries in the Val d’Orcia. Keep in mind you may need to make reservations.
Great resource. Alcohol limits in Italy are much lower than here.

https://www.winewordswisdom.com/travel_itineraries/southern-tuscany-wine-tour.html

https://www.winewordswisdom.com/wine_reviews/chianti-classico-tasting.html

Some more towns to visit.

Acquapendente, (E- Borgo village), Radicofani (E-Borgo village,( well persevered Fort) Castiglione d’Orcia, (fantastic views from the top of town, quaint village) Bango Vignoni, Monticchiello (classic curving road with cypress trees lining it all the way to the village) Montepulciano (some of the best wines) Montevarchi another E-borgo.

Thank you for your suggestions. We decided to take the SR 2 to Siena and spent about and hour and a half having lunch and walking around. We look forward to returning to Tuscany and doing a proper winery tour. Cheers!