Introduction to the city of Cortona
From upper left corner: Volterra, Greve in Chianti, San Gimingnano, and Siena (two)
I must say it was difficult for me to identify a favorite Tuscan city until visiting Cortona, but as my criteria for inclusion relies on the intangible, the almost ethereal power that comes from a place, and I knew after spending only a day that it was special. You know when you experience an almost immediate, overwhelmingly positive response to a place? Visit Cortona and find out! I respect Florence but I do not love it. I found Arezzo, Siena, San Gimingnano, Pisa, Greve in Chianti, Volterra and Montepulciano particularly lovely. Yet, when I finally reached Cortona I found my holy grail in the region of Toscana.
Cortona hosts multiple food festivals in largely popularized by the success of the book and subsequent feature film, Under the Tuscan Sun by Frances Mayes. The book is more instructional than the film, peppered with useful recipes amid the narrative; I do recommend it, especially if you take my advice and visit Cortona. Regardless, Cortona is a city you can visit and enjoy because of the connection with Francis Mayes’ memoir or in spite of it. The picturesque Tuscan town has not become a caricature a mockery of itself due to the success of the feature film with Diane Lane. However, if you want to experience the Tuscan Sun ‘alla’ Diane Lane, there are tours to seek out both in person and online blogs that highlight featured spots, such as where her villa was located outside of the city. Blogs, such as this one, trace locations of the film.
My point is the city has maintained its authenticity and would complement a visit to Florence and serve as a home base for exploring the rest of the region.
A view of Lake Trasimeno from Cortona
In my experience, the town offers the perfect balance, the quintessential Tuscan experience. Set high on a hilltop, replete with medieval streets to explore, but Renaissance art and architecture as one would expect from the region, Cortona also boasts impressive views over the Val di Chiana with gorgeous viewpoint for photo opportunities. You will be able to admire the Lake Trasimeno from this vantage point.
The town, although overwhelmingly medieval in appearance, has origins that date back to the Umbri (an ancient group of Italic people) that were then conquered by the Etruscans and called the city Curtun. In the 13th century Cortona became a city state and was later controlled by the Medici family in the early 15th century.
Up to this point, I have only alluded to the ‘culinary’ aspect of this city with the food festivals (Here is the festival schedule); however, one of the most compelling reasons I chose Cortona over many other worthy Tuscan towns is la cucina. The restaurants I researched and ate at in Cortona were exceptional in regard to cuisine, service and ambiance. Visit these restaurants, and without much effort, you will have an authentic taste of the celebrated food from this region.
To finish, I want to warmly recommend our Airbnb, which felt like the perfect Tuscan farm home. We had the best of both worlds, however, because it was centrally located in the heart of the city center. This means, lest I remind you, that it is situated on a steep hill, however, so do keep this in mind regarding mobility. Your heart rate will spike on the ascent. Of course, I am not sure if the configuration will suit your personal accommodation needs, but we were very pleased. Update 2023: It seems like the owner has removed the listing from Airbnb and put it on alternative ‘Rent by Owner’ websites. Here is the current listing; it is called Casa Iolanda. However, there are lots of great Airbnb and VRBO options here. We took the train in from Rome and actually missed the nearest station to Cortona. Our gracious host picked us up from the next train station and drove us directly to the house. This set a precedence for a wonderful weekend full of hospitality and tranquility in a gorgeous two-story Tuscan home with a view of rolling hills from most windows. If you do like Under the Tuscan Sun, you will feel like Frances in this house.