Cortona, Italy: The Gem of Southern Tuscany

Things to do in Cortona, Italy

Even without the fame from the book and film ‘Under the Tuscan Sun‘, Cortona, Italy, has quite a reputation. This small town in southern Tuscany has a rich history full of legends, ancient populations, battles, religion, and art, making it a great stop on any trip to Italy.

The town is enclosed by stone walls dating back to Etruscan and Roman times and sits high on top of a hill overlooking the beautiful surrounding Val di Chiana. This makes it one of the more remote locations you can visit.  

1. Basilica di Santa Margherita

As you make your way to Cortona, you can already see the Basilica of Santa Margherita peering down on the surroundings from the very top of the town. This ancient church is a shrine dedicated to the figure of Santa Margherita, patron of Cortona and Franciscan tertiary.

The church was originally built by the Monks in the 11th century but got severely damaged during a siege by neighboring town Arezzo. It was Margherita di Cortona who led the efforts to rebuild the ancient church, which measured 15 meters long. After her passing, another church was built in her honor, right next to the old one. What you see nowadays is the old and new church merged together, with beautiful details and about 30 meters long. 

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You can visit the church by taking a short walk or driving up the hill from the town of Cortona, and the entrance is free.

2. Piazza della Repúbblica

In the heart of the town lies the main square, Piazza della Repúbblica. This location has been the center since Roman times when it was used as a marketplace (known as a Forum). Nowadays, it is a crossroads flanked by shopping streets and alleys leading to the town’s quintessential corners.

Right in front of the square sits the Palazzo del Capitano, an impressive stone building with a wide staircase. Take a moment to sit on the steps and enjoy some people-watching, or grab a table at one of the cute outdoor cafes for a delicious cappuccino. Piazza della Repubblica is the liveliest spot in town and one of the best things to do in Cortona.

3. Explore the Medieval Streets of Cortona, Italy

While Cortona has some interesting historical highlights, the entire interior makes it an amazing location to visit in Italy. Between the many churches, monasteries, and piazzas, you can spend hours exploring the town, wandering through its narrow shop-laden streets.

There are lots of local shops with handmade items, popular museums, and a few delicious Michelin restaurants. Getting lost in this maze of little alleyways is one of the best things to do in Cortona, Italy.

Discover the town’s secret little corners, only stopping to take some photos or look out over the stunning views of the valley below. From the town, it’s even possible to see Lake Trasimeno in Umbria! 

4. Visit Convento delle Celle

About a 10-minute drive outside of Cortona’s walls, in between the trees, lies the Franciscan Monastery Le Celle. This impressive sacred building was built at the turn of a narrow valley around 1211, isolated from its surroundings. Because of this, there’s quite a spirituality to the place, allowing visitors to explore the site in tranquility. The building and the surrounding nature are equally impressive, with stunning views over the Chiana Valley below. 

The Franciscan convent Le Celle was the first monastery built by Saint Francis of Assisi, one of the most revered religious figures in Roman Catholic history. Over the years, the stone building has been reconstructed several times and is now inhabited by a small brotherhood of friars (monks). You can visit the monastery by car or on foot (40 minutes) from Cortona, accessing it through a stone pedestrian bridge that crosses a small stream. 

5. San Francesco

Another historical highlight of Cortona, Italy, is San Francesco, a 13th-century Roman Catholic church located in the heart of the town. This religious building is yet another piece of the Franciscan puzzle. It’s one of the first Franciscan churches to exist, the burial place of Saint Francis, and home to some of his precious relics. 

While you walk through the cute alleyways of Cortona, you’ll surely come across San Francesco, recognizable by its large circular window on the facade. It’s dramatically changed over the centuries but still shows some signs of its original beams and beautiful frescos. The greatest treasure, however, is a shrine of the True Cross, a Byzantine ivory tablet bought from Constantinople. Take a look inside to see the relics and the distinguished artworks that the building houses, soaking up the history of the place and town.

Best Cafes and Restaurants in Cortona

No visit to Italy is complete without having taken advantage of the incredible food scene. There are many great restaurants in Cortona that offer traditional local and Tuscan cuisine. From Michelin star places serving wild game to little osterias famous for their breakfast stew, you’ll never tire of finding a great place to eat. Some of our favorites places were: 

How to Visit Cortona, Italy

Located further into the countryside, Cortona is a great destination for visitors looking to explore the more rural areas of Italy. The town lies only a short drive from other interesting locations such as Arezzo or Montepulciano, making it a great stop when driving through Italy.

To get to Cortona, you’ll need to fly to one of the major airports in Italy, for example, Rome, Pisa, or Florence.

Discovering Italy by car is the most flexible way of traveling the country. Note that parking within Cortona’s walls is limited. You’ll have to pay attention to the off-limit ZTL zones (Zona Traffico Limitado).

If you’re traveling through Tuscany without a car, it’s possible to add an organized tour to your itinerary, which includes a visit to Cortona. Many of these run from larger cities like Florence and include visits to other places in Tuscany.

Alternatively, direct regional trains run between Florence and Rome, stopping at the Camucia Stazione near Cortona. There are also frequent trains that depart from Arezzo to the same station. From there, you can either walk or take the local bus into town. The bus regularly runs seven days a week year-round.

Getting Around 

Cortona, Italy, is a fairly small town that you can easily explore on foot. If you’re traveling by car, it’s best to park outside the town walls and walk from there. Otherwise, always look for a place where you’re certain you can park. Learn more about renting a car and driving in Italy.

Where to Stay in Cortona, Italy

Cortona makes a perfect location for a day trip when traveling through Tuscany. However, spending the night gives you an even better understanding of how this small Italian town lives up to its name.

Our favorite hotels in Cortona 😴

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Monastero Di Cortona Hotel & Spa

Cortona

Casa Dreosti

Cortona

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Cortona

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Choose a small guesthouse or bed&breakfast in the center of town, or spend the night out in the remote countryside. See all hotels in Cortona.

Best Time to Visit

In the summer, Cortona organizes the Tuscan Sun Festival, an annual arts festival in the last week of June that several international stars and artists love to join.

The rest of the summer can also be relatively busy still. Because of this, we recommend visiting in April/May or September/October. Both these times will still be warm, allowing you to enjoy the fantastic sights of Cortona and its surroundings.