Stop between Umbria and Firenze
 

Planning to drive from Umbria (Todi) to Firenze and looking for a nice town to explore for a couple of hours and have lunch some place along the way. Will have visited Orvieto, Perugia, and Assisi on this trip and Siena, Montepulciano, Pienza, Montalcino 2 years ago. Thinking of stopping in Cortona or Arezzo? Perhaps Gubbio or Sansepolcro are worth a detour? If one were to choose Cortona vs Arezzo. which would you pick? Any other suggestion for nice villages or castles along the way would be most welcome.

San Gimignano?

It's admittedly not the prettiest of Umbria's towns, but if Italian ceramics interests you at, I would recommend Deruta as an interesting stop. We've bought some beautiful pieces there.

I enjoyed Gubbio, but it is significant detour. Montefalco (lunch at L'alchemista) and Bevagna would be closer, attractive detours.

What about the chianti trail? You could stop at a winery and explore the small towns, Gaiole in Chianti, Radda, Greve...book a tour and lunch at Castello di Ama...

I also suggest Chianti.

Have you been to Abbazia Monte Oliveto Maggiore?

https://www.discovertuscany.com/what...-maggiore.html

Between Cortona and Arezzo, I would prefer Arezzo. However, that may be attributed to my own personal interests. Arezzo is a larger city than Cortona. The Church of San Francesco has a beautiful fresco cycle, the Legend of the True Cross, by Piero della Francesca. Under the church, there's a little museum that had an interesting exhibit the last time we were there. On the first Sunday of every month, and the day before, Arezzo has an outdoor antiques market, which we enjoyed.

There are three possible routes, all of which take nearly the same amount of time, to Florence from Todi. The northernmost, the SS3, passes right through Città di Castello, and is the nearest to Arezzo. Gubbio wouldn't be terribly far out of your way if you took this route. Sansepolcro would also be near the route. Piero della Francesca was born in Sansepolcro, and there are several of his works there, but I don't know if you're interested in this Early Renaissance painter.

The southernmost route takes the SS448 from Todi and joins the E35. This would take you right through Orvieto and fairly near Montepulciano and Pienza. Montalcino wouldn't be very far off the route, and you'd also pass near the Bolsena lake. Near Arezzo, this route joins the northernmost route, so you could also easily stop in Arezzo.

The middle route is the same as the northern route as far as Perugia, where you would take the Raccordo Bettole-Perugia to cut across to the E 35 north of Lake Trasimeno, and from there on it's the same as the southern route. This route would allow you to stop somewhere along Lake Trasimeno. There are some very small towns here. The only ones I've heard of are Tuoro sul Trasimeno and Passignano sul Trasimeno. We stopped in one of these towns once, but I don't remember which one. There are some nice lake views along the road. This route would also pass a little closer to Cortona than the others, and would be just as convenient to Arezzo as the southern route.

Orvieto (duomo) and Chiusi (Etrscan museum and tombs).

I would not choose Sansepolcro if I wasn't interested in Piero's works. If you are, it is a perfect lunch stop. But be aware that the town is very quiet over the early afternoon. Be sure to check the timing of the museum if you go there. We had a good lunch in town, but I can't remember the name of the restaurant.

I too like Arezzo and have been a few times. The antique mart and the Piero works were our draw. It is a much larger town and maybe a bit harder to visit for a short time. Although we did take friends for a few hours during the antique market. They enjoyed it.

Thank you everyone for your suggestions. We have to leave Todi around 10 am and make it Firenze around 3pm. Given about 2.5 hours of driving this gives us enough time to visit one town/village, explore it, enjoy lunch and drive to Firenze. We are looking for charm/art/culture/history combination, and given our restrictions I am leaning towards Cortona. Geographically either Arezzo or Cortona are the easiest. Montefalco area we will have visited before, as well as Orvieto, Montalcino, Pienza, Montepulciano area. Always wanted to go to Abbazia di Monte Oliveto Maggiore but I think this would be too much detour for what it is.
San Gimigiano is too touristy, I think. Chianti is nice, but as for wine, I much prefer Montalcino.
Piero's frescoes (and perhaps Casa Del Vasari) would be the reason to go to Arezzo. The downside that I sense that Arezzo itself is not that pretty or pleasant to walk around and the drive up is not pretty either.
Cortona does not have Piero's works, and has more tourists. On the other hand the road and the town are pretty, and there a museum with Renaissance works.
Is my reasoning flawed?

I like Arezzo but would pick something smaller if you're just planning a short-ish stop.

The Sodoma frescoes (Life of St. Benedict) in the cloister at Abbazia di Monte Oliveto Maggiore would be worth a detour for me. The last time we were there, the organist was practicing, so we got to hear a free concert too. But visiting the monastery requires careful planning because the entire place closes in the middle of the day. There is a restaurant at the main gate.

http://www.wga.hu/html_m/s/sodoma/monteoli/

http://www.monteolivetomaggiore.it/lang1/cloister.html

I think Castellina and Radda are good lunch-and-a-walk stops in Chianti. Castellina has a little nice shopping. Radda is especially easy because it has no ZTL. The drive to Radda is very scenic, and the length of SR222 from Siena to Florence (passing through Castellina) is called Via Chiantigiana.

http://www.chianti-italy.com/chiantigiana.htm

Also on 222, Panzano is a good choice too.

San Gimigiano might be a bit touristy but that is because it is absolutely wonderful IMO.

Are there any nice areas to picnic some place between Perugia and Firenze?
Any place where we can pick up picnic food along the way?

There happen to be groceries in every medium sized village, that means every few miles.
Nice places where people can pic nic are omnipresent, but certainly not along main or secondary roads.

San Gimignano is certainly worth the trip, and I wouldn't be terribly bothered by the crowds in the streets. However, when we drove there once in late April, cars were being turned back on the approach road because there was no place to park. We had to park alongside a country road and hike in. I would definitely not go on a weekend. Oddly, the police officer who stopped us addressed us in English, in spite of the fact that we were driving our own car with Italian plates, and that I was holding an Italian language tour guide. Maybe it was because my husband was wearing white tennis shoes?

I quite like Arezzo myself. I consider it a quintessential Tuscan town, unlike the tourist image of the region. The Church of San Francesco is on the outskirts of the town, and is easy to visit on a short stopover.