Cortona in July

Well, the last one is easy:

Get money from an ATM when you arrive in Europe. Unless you're headed to Svalbard or some other place at the ends of the earth, any airport you arrive at is going to have ATMs where you can easily and reliably pull cash from your home bank/CU account for nearly nothing. It's the least expensive, easiest, and most obvious way to go.

IMHO the idea of exchanging money, or jumping through expensive hoops at home to "order" euros prior to a trip is an anachronism akin to travelers checks and steamer trunks. Kiss those things goodbye.

Since you've been to the area before, I'm wondering if you've been to Perugia and Arezzo? Beautiful and interesting towns. We also will be back in the area (near Castiglione del Lago) in the Fall, and I want to go to Gubbio too, as well as Spoleto. Other places within reach are of course Siena and Lucca.

Enjoy your trip!

Go east into Umbria on day trips- Perugia, Assisi, Spello, Montefalco, Bevagna, Todi. Beautiful area, less crowded than Tuscany.

Gubbio is a very charming medieval village/city and worth seeing.
Agree with other suggestions talking about Arezzo(la vita e bella was shot there in part) Perugia has a great piazza, nice museum.
Assisi is also fantastic, cathedral is more than a must.
Have a great trip
Claude

We stayed in a luxury small resort outside Sinalunga, but the town didn't look that special. Near Cortona I recommend Castiglione del Lago and high-end lunch and tour of Aviognesi winery.

All the towns Suki mentioned are very nice. We visited some of these while staying in an agriturismo outside of Montepulciano and some of them on another trip staying at an agriturismo outside of Assisi.
Bevagna and Montelfalco were very untouristy. From Assisi location we also went to Civita di Bagnoregio stopping at Orvieto on the way back.

In addition to what already mentioned above, from Cortona you could visit the following destinations, mostly in the same province of Arezzo as Cortona, which are even much closer than what suggested above.
In order of proximity from near to farther from Cortona:
Castiglion Fiorentino
Lucignano
Passignano (Umbria)
Castiglion del Lago (Umbria)
Arezzo
Anghiari
Poppi and the Casentino Valley

Except for Poppi, all others are within 20 to 50 min drive.

Anghiari and the city of Arezzo (the provincial capital) are a must see in the province, if you ask me.

I can add Anghiari is lovely and small. We saw that with Arezzo last year. Arezzo was great too, wish I had spent more time exploring there. Can't say how it compares to others on this list but we will also be staying in Cortona this fall as we really enjoyed the area. So I guess we will find out.

As mentioned above, Academy Award winning movie “La vita è bella” (Life is beautiful) by Roberto Benigni, was shot primarily in Arezzo’s city center. However one scene where Mario meets his future wife under heavy rain, was shot in Cortona, in front of the Teatro Signorelli. Some other scenes were shot in and around Castiglion Fiorentino. If you are interested there are tours in Arezzo visiting the filming sites. Maybe you should rent that movie on Netflix before going.
Roberto Benigni was actually born in the area, in the village of Misericordia, in the municipality of Castiglion Fiorentino.