3 weeks in Umbria and Tuscany June 2022

There is a current detailed series of posts on this subject on Fodors.com, go to Europe Forum.

Read this thread... https://community.ricksteves.com/travel-forum/italy/most-beautiful-small-villages-of-italy

Let me suggest at least a day in Montepulciano. We stayed 2 days, and it wasn't long enough. The Caffe Politziano is probably the most beautiful restaurant I've ever seen. There are interesting side streets, shops, public buildings.

For your Umbrian base: Assisi, Gubbio, Norcia, Perugia city, Spello and Spoleto.
For your Tuscany base: Buonconvento, Castelnuovo dell’Abate, Montepulciano, Monticchiello, Pienza, San Gimignano and Siena.

Here are some nice drives from your locations, we’ve done these in over 6-7 trips in Tuscany.
Our base locations were slightly different, but close to yours. Drive times between towns is included. You should be able to visit 2-3 towns a day. Many of these towns are UNESCO world Heritage Sites or e-Borgo villages.

Assisi-Spoleto 38min -Trevi 22min - Spello 19min -Assisi 18min.

Assisi-Montefalco 35min - Bevagna 10min-Deruta 28 min-Assisi 31min

Assisi-Gubbio 40min- Perugia 42min-Assisi 29m

Assisi-Cortona 1H -Assisi 1H05m. Or
Assisi-Anghiari 1H15m-Cortona 49m-Assisi 1H05m.

Assisi-Arezzo 1H28m -Assisi.

From Pienza

Pienza-Montepulciano 20 min

Pienza-Castellina 1H27m.

Pienza-Siena 1H05min.

Pienza-Castiglione d’Orcia 26min - Bango Vignoni 13min -Montiecchiello 20min-Pienza 15min.

Pienza -Cetona 52min -Sarteano 11min -Pienza
41 min.

Pienza-Acquapendente 49min-Radiconfani 28m
Optional stop (Bangi San Filippo 16min outdoor hot springs)-Pienza 34min

Pienza-Sant’Antimo Abbey 39min- Montalcino 20 min - San Quirico d’Orcia 15min - Pienza 27min.

Pienza-Gaiole 1H17m- Castelnuovo Berardegna
27min-Pienza 56 min.

Hope these help.

Instead of renting a car at the airport, take the train to Orvieto. Do get at least one good night of sleep before renting a vehicle. Do not expect to sleep on the plane. Even if you doze off, I doubt if it will be enough sleep to operate a car in foreign land with strict speed and ZTL zone laws. Make sure you’re up to date about driving in IT before departure, otherwise, you could be fined.

Totally agree with MaryPat, take the train to Orvieto. Driving after a flight is like driving under the influence. It’s a 2 hour drive, don’t take chances.

For comprehensive info on driving in Italy, use this:
https://italybeyondtheobvious.com/custom-italy-vacations/our-5-step-process/

and download their e-book, click on banner at the bottom of the page.

Thank you to everyone for your help and great suggestions! AWESOME!

First about the car.....we looked into training to Orvieto, but we could not get a car there with AutoEurope. We would have to train to Chiusi to get one. That made the car rental way more expensive because we are taking the car back to Rome Fiumicino Airport rather than Chiusi. But I will look into again and thank you very much for your excellent suggestion. FWIW... we prefer AutoEurope car rentals. Never had a problem with them, and you can buy the zero deductible insurance ahead of time and avoid the hassle when picking up the car. We have researched other companies and we still couldn't find a rental in Orvieto. But will try again. If we can rent a car in Orvieto will we need to go into Rome to get a train to Orvieto? Thank you, kindly?

Thank you for the the day driving routes to various villages from our 2 bases. So kind of you! Cant wait to study the further!!!

Thanks for the links to "Italy Beyond the Obvious". Very helpful driving tips! Thank you one and all!

Happy Travels, Monica

You can catch a regional train from the FCO station to the Roma Tiburtina station then onward to Orvieto.
It won’t save any time, but it is a smaller station.
Travel time is still about 2 hours.

Here’s another thought...

If you do decide to rent a car at FCO, this town is a 35-40 minute drive from the airport.
Edit Spend the nite here.

https://www.througheternity.com/en/blog/travel-tips/day-trip-to-bracciano-from-rome.html

On the way to Orvieto, head to Viterbo. Civita Bagnoregio is 15 min from there.

Orvieto has a car rental across the street from the train station. Don't remember which company, though.

Orvieto has a Hertz office, but you have to book directly through Hertz. Auto Europe doesn’t work with this office.