If you had to had to choose between Orvieto vs Cortona, which would you select? I am hoping to squeeze in time to see both if we find we are moving around too much we may opt to omit one less town. We have a car and only 5 nights in Tuscany. Here is our plan: Stopping at Civiti di Bagnoregio on the way to our base in Montepulciano. Spending 1st evening + one full day in Montepulciano; then 1 day in Montalcino w/a stop in Pienza (and possibly San Quirico) on the way. Then one day in Orvieto and another in Cortona (w/possibly a winery stop on way back). Do you think this is a doable or is it going to be too much? If too much, which should I omit? Would love some help deciding. Thank you.
PS: driving from Sorrento so not enough time to visit both Civiti di Bagnoregio and Orvieto in same day.

I have never been to Cortona, but I was just in Orvieto in October and I found one day sufficient to see the Basilica and the town.

Orvieto is s cute hill town, but there isn't that much to see. It is a good place for pokey parkers. If you like gift shops, you will love Orvieto.

Thin

We spent a week in Cortona and a day in Orvieto. Cortona has the Eremo le Celle of St.Francis on it’s hillside which we found very interesting .You can see Lake Trasimeno from the top of Cortona. The Duomo in Orvieto is magnificent. Orvieto is in Umbria and Cortona in Tuscany but on border of Umbria. Both are surrounded by wineries. You can’t go wrong.

I've been to both and enjoyed both but prefer Orvieto (been there twice, for a few days each time). Cortona I did as a day trip. But you could see each of them on a day trip if that's all you have. I think Orvieto is more unique.

What are you after? We travel for art a good deal, and I would pick Cortona. Also look for St Francis sites, so again, Cortona.

Sounds like I'll have to try to hit them both spending a day in each if at all possible. Thanks everyone for your input.