Oh Cortona...how I love thee so. Most people know of this town because of the famous book/movie from France Mayes (who still has her famed Bramasole Villa tucked up in the hills above Cortona), it's popularity shows on any day during the summer by the throngs of tourists cruising down via Nazionale.
When I lived in Italy during my internship, Cortona was one of the easiest towns to get to from Castiglion Fiorentino. It was a convenient bus trip away from the convent when we didn't have a lunch shift, but close enough that we could get back in time to work the dinner shift! Plus at the time, the bus picked us up at the top of our hill and dropped us off at the top of Cortona in Piazza Garibaldi! Win!
You'll hear quite a bit of English in this town too, not just from tourists. Cortona hosts a popular study abroad program for the University of Georgia. Similar to Castiglion Fiorentino, you'll find a many expats who met their spouses while studying abroad in Italy!
While it's a lot more crowded than it used to be, Cortona is still worth a visit for some shopping, dining and sketching!
Further down via Nazionale, you'll find lots of charming shops, selling everything from leather purses, antiques, soaps, and olive oils. There's a few art galleries that you can peek into as well! There are even a few spots that offer tastings of their locally made limoncello, dessert liquors, cantucci and wine!
Past Piazza dell Repubblica, you'll find some more charming shops and if you keep going north, you'll eventually come to the north wall of the city! Via della Mura del Duomo has a great view of the valley and cemetery below Cortona, and the road that leads to Le Celle, the Franciscan Hermitage that Saint Francis spent some time at! If you want a peaceful walk after lunch, consider meandering back to see this holy and quiet place.
Also along the north end of the city you'll find a few museums. The Diocesan Museum has some great pieces from famous artists from the area, and it's right next to one of our favorite views of the city. The neighboring church in this piazza is free to visit too, a great spot for a break from the sun, wind or rain.
If you're feeling really ambitious, consider making the trek to the top of the city to visit Santa Margherita, the church of the patron saint of Cortona! It is a TREK but if the little old ladies of Cortona can do it, you can too! It's a wonderful church with a great view of the valley below!
After you've had your aperitivo, it's time to start planning where you want to eat dinner! We have a few favorite restaurants besides Enoteca Enotria. If you want something a bit pricier and fancier, you should consider Ad Braceria. It's tucked down an alley and feels like you're dining in an ancient wine cellar! So delicious and so unique. Another favorite of ours if you want to dine outside if Fufluns. They make a very delicious pizza and are just a fun spot to have a dinner late into the evening.
By now, it's probably time to head back to your hotel but Cortona is also a lovely city to wander through at night. Especially during the summer...once the heat of day and tourists disappear, the cooler temperatures and magic of this tiny city comes back!