Cortona on a Sat/Sunday

My husband and I spent a week in Cortona a couple years ago, and it is a beautiful little town. Be forewarned that it is on a steep hillside, and while the mainstreet is relatively flat, walking through the town to any of the 33 amazing churches there can be a challenge. At Santa Chiara, there is Mass every morning at 8:00 where the sisters of the convent sing part of the Mass. They truely sound like angels! There is a nice hotel, the Hotel San Michele that is a 15th century historical building located in the heart of town. It looked very nice and clean, and although we did not stay there, we would try it on a return trip. It is across the street from the Piazza Repubblica. One of our favorite things to do was to sit on the steps of the Piazza Repubblica with the locals in the evening and watch all the people, like the local children playing a game of hide and seek. There is not much that is touristy there, and to find places to eat, we just followed the locals. Bar 500 Cortona is a great place to sit outside and enjoy a snack or light meal. The owners couldn't be nicer, and they have a bulldog named Nellie that will steal your heart. Because it is a small town, understand that from about 1:00 to about 4:00, most of the shops (except the restaurants) close up to go home for lunch and a napso we did the same, then at 4:00 the town is alive again and by 6-7, the passegiata is underway where the locals stroll up and down Via Nazionale, the main street in Cortona to visit and shop. As you know, this is the town written about in Under the Tuscan Sun, and if you haven't read it yet, I highly recommend reading it before you go. It will enrich the time you spend there. Enjoy your trip!

We stayed at Villa Marsilli, great hotel. Just take the day and walk the streets. You will love it. Go to San Francesca, and Under the Tuscan Sun villa.

Cortona's market day is Saturday, so that should work perfectly for you! Make sure to leave room for a porchetta sandwich at the market - yum. Also, as an Under the Tuscan Sun fan, take the walk to Frances Mayes' house. If you time it so you are walking back to town from her house around sunset, it's GORGEOUS. I stayed at the Hotel San Michele and it's really centrally located in town. Driving up to the hotel to drop off your luggage is . . . interesting . . . but, from experience, it's a lot better than dragging it up the steep streets. You'll definitely get a good workout in Cortona. In terms of food, we ate at a bunch of places, including Trattoria Dardano, La Bucaccia and La Loggetta.

Thanks Michelle and Gordon, just the kind of information I was hoping to receive. Do you know if there is a market on Saturdays??? I have read Under the Tuscan Sun....maybe 3 times now. I love to wander around a town stopping when I see something interesting. Sounds like this town is perfect for that.....
Thanks again. If you think of anything else, more is better.....

I stayed at Hotel Italia, a little closer to the Main Street but very quiet. Cortona is a big art town, lots of artists have galleries and some workshops you can visit.

We spent a whole Saturday in Cortona, but by the time we arrived, the market was at an end. After wandering up to the church at the top of the town, we saw several weddings in progress which was fun. Every time Under the Tuscan Sun in on TV, have to record it and watch it a couple more times. Read the book also, as the story line is very different than the movie.

Do you remember the approx. time the market started to shut down? That would be great to attend. We would be arriving from Orvieto, so that would be good to know. Seeing the artist workshops and displays would be wonderful as well. How about Sundays, other than the nun's singing mass, are any of the small shops open after church in September? Or special fiestas?
You all have been most helpful, thanks......

A few years ago while driving to Le Marche, we stopped in Cortona on a Sunday afternoon on a whim, hoping a few things might be open. It was very much alive! Lots of galleries and shops were open on that main street leading up to the central piazza. Trattoria la Grotta had lovely little brick-ceilinged dining spaces, good food, and friendly waiters. Lots of steps and picturesque back alleys.