Cortona: An Evening Stroll in Tuscany, Italy

Hello my friends. In this post I’ll share our visit to Cortona, a small town in Tuscany. We tasted local, unique pasta dishes and delicious meat specialties, then wandered the city streets at night.

We were on holiday with my family near Lake Trasimeno, on the border of Umbria and Tuscany. That day our destination took a different direction. We decided to head to Cortona, a hilltop town 500 meters above sea level, for dinner. Once again, we were prepared to walk up and down the stone streets of the old town.

We set off from Lake Trasimeno, where we were staying and decided to have dinner in the historic town. Along the way we enjoyed an incredible sunset. However, driving on the mountain roads can be a bit intimidating, especially for first-timers. Even worse, although there are many parking lots at the entrance of the old town, all were full. We finally found a spot in a paid parking area and had to walk uphill to reach the old town.

Cortona is an impressive place with typical medieval architecture. Gray stone buildings, narrow cobblestone streets, small artisan workshops and classic Tuscan restaurants fill the town. Around the city you’ll find sites with rich history, castles, medieval villages and enchanting trails for long walks. When I think of Cortona, the first things that come to mind are the stunning views from its terraces and the beautiful squares like Piazza Luca Signorelli and Piazza della Repubblica. I’ll also never forget the clock tower at Palazzo del Capitano and the delicious Tuscan cuisine paired with local wines.

We only had one evening to spend in this magnificent place, so we didn’t get to see everything. If you visit Cortona, you can explore the historic city center, discover the Museo dell’Accademia Etrusca, visit the Eremo Le Celle monastery and the Fortezza di Girifalco fortress and see Santa Margherita Basilica along with the Parco Archeologico del Sodo.

As someone fascinated by old churches, I must recommend seeing the Church of San Maria delle Grazie del Calcinaio. It’s located on the outskirts of the town, but when we passed by, it was either closed or under renovation. Cortona also features the Santa Maria Nuova Church and stunning villas like Villa Bramasole and Villa Giamelli. Since Cortona is an ancient city with Etruscan origins, I highly recommend visiting the Etruscan Stone Tomb and the remains of Locanda della Pietra. Though a small town with a population of around 22,000, Cortona offers many interesting places to see and explore.

Walking through Cortona is a sheer delight. Taking in the breathtaking views of the valley from the terraces, admiring the dark gray stone buildings, uneven cobblestone streets and the restaurant tables lining the streets. it’s a feast for the senses. But beware, tables often occupy much of the pedestrian pathways, so you’ll need to navigate carefully to avoid bumping into tables or diners.

I find the streets and squares very intriguing. While walking, you can watch tourists enjoying their meals or observe passersby while dining al fresco. Even when I dine indoors, I usually choose a seat by the window so I can watch people outside and the occasional car passing by. 😊

Cortona's beauty has captivated not only tourists but also directors and film crews. For instance, parts of the movie Under the Tuscan Sun were filmed here.

After strolling through the town, we found a lovely trattoria and enjoyed a delightful meal. The menu featured pici, a traditional Tuscan pasta. A friend had specifically recommended that I try pici all’aglio (garlic pici). We also ordered various meat dishes and local wines. Everything was incredibly delicious. Pici is a type of pasta unique to Tuscany. It resembles round, slightly thicker spaghetti but isn’t hollow. The taste is simply amazing. After dinner, we continued our walk, stopping by a few elegant shop windows. 😊

Driving into Cortona's old town is prohibited as it falls under a ZTL (Zona a Traffico Limitato or Traffic Restricted Zone). Once I received a fine just for briefly stopping at an intersection to pick someone up. I didn’t even enter the old town, but the camera mistook my pause as an “entry” and I ended up paying a fine. So, be cautious.

The main square in Cortona is filled with restaurants and outdoor tables. It’s a fantastic place where you can enjoy your meal while soaking in the atmosphere of the square. The Palazzo Comunale building, with its historic stone and brick architecture, exudes a quintessential medieval vibe.

Cortona’s narrow streets, sloping up and down, reminded me of Montefiascone in the Lazio region. We stayed there last year and it’s also perched on a hill with similarly structured streets. Even though it was already dark, the city’s atmosphere was incredible. We eventually made our way to a viewing terrace and saw a church made of dark stone. It was an impressive structure.

I also noticed Andrea Roggi’s sculpture titled The Tree of Life and Productivity displayed there. If I’m not mistaken, his works were previously exhibited in Monte as well. Whether they’re still there or not, I’m unsure, but seeing some of his art displayed here as part of a street exhibit was fascinating.

And there’s an old building here that adds to the historic ambiance. The square’s texture and captivating atmosphere draw you in. Our main reason for descending to this square was to take in the valley view. When we first arrived, I had briefly glimpsed the valley and the viewing terrace. However, when we returned after dinner, the darkness had hidden the scenery. The mountains, valley and even the lake, which should have been visible in the distance, were all shrouded. Yet, the valley at night, illuminated by lights, had its own unique charm.

Cortona’s compact and cozy layout made me curious about how it would look during the day. If we have the chance, we’ll try to visit again in daylight.

After our evening stroll we returned to our holiday home on the shores of Lake Trasimeno in Umbria. We had rented a house there for our vacation. By the way, during this trip, we visited several other towns around the lake. I’m preparing separate posts about them, which I’ll publish soon. See you again soon. 😊