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 in Tuscany, Italy, has quite a reputation. It’s full of legends, ancient populations, battles, religion, and art. We loved walking through the historic town, peering out over the surrounding Val di Chiana.

1. Basilica di Santa Margherita

As we made our way to Cortona, we could already see the Basilica of Santa Margherita at the very top of the town, peering out above its surroundings. This ancient church is a shrine dedicated to Santa Margherita, the patron of Cortona and a Franciscan tertiary.

The church was originally built by the Monks in the 11th century, but got severely damaged during a siege. Margherita di Cortona led the rebuilding of the ancient church.

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! How to visit: take a short walk or drive up the hill. Admission is free.

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2. Piazza della Repúbblica

In the heart of the town lies the main square, Piazza della Repúbblica. It’s the liveliest part of town, and has been the center since Roman times, when it was a Forum (a marketplace). Nowadays, it is flanked by busy shopping streets and cute alleys.

At the square, you can see:

• Palazzo del Capitano: an impressive stone building with a wide staircase lining the square. Take a moment to sit on the steps and enjoy some people-watching.
• Many cute outdoor cafes where you can grab a yummy cappuccino.

3. Explore the Medieval Streets of Cortona, Italy

We loved roaming through Cortona; it’s an amazing place to visit in Italy, with lots of historical highlights. Between the many churches, monasteries, and piazzas, we spent hours exploring the town, wandering through its narrow shop-laden streets.

Fun Fact: Cortona is also supposedly the birthplace of the founder of Troy (Dardano), whose descendants eventually left Troy and founded Rome! You’ll spot the name all over the area.

There are many local shops selling handmade goods, popular museums, and a few Michelin-starred restaurants. Getting lost in this maze of little alleyways is one of the best things to do in Cortona, Italy. From the town, it’s even possible to see Lake Trasimeno in Umbria! 

4. Visit Convento delle Celle

Just outside of town, in between the trees, lies the Franciscan Monastery of Le Celle. This impressive sacred building has a beautiful sense of spirituality about the place. We loved the views over the Chiana Valley below, wow! Getting there: 10 minutes by car, 40 on foot.

The convent was the very first monastery built by Saint Francis of Assisi, one of the most revered religious figures in Roman Catholic history. It’s been reconstructed over the years and is now home to a small brotherhood of friars (monks). Open: Daily from 7 AM to 7 PM, entrance is free. 

5. San Francesco

Another highlight of Cortona, Italy, is San Francesco, a 13th-century church right in the center. While browsing the cute alleys of town, we recognized it by its large circular window on the front. It’s dramatically changed over the centuries, but it still shows its original beams and beautiful frescoes.

Its greatest treasure, however, is a shrine of the True Cross, a Byzantine ivory tablet bought from Constantinople!

Best Cafes and Restaurants in Cortona

It wouldn’t be a visit to Italy if we didn’t take advantage of the incredible food scene. Cortona has many great restaurants with delicious local and Tuscan cuisine. We had the best dinner on the outdoor terrace of Osteria del Teatro!

Some of our other favorite places were: 

How to Visit Cortona, Italy

We added Cortona as a cute destination to our Tuscany road trip. It lies only a short drive from other interesting spots like Arezzo or Montepulciano. We flew into Florence and rented a car from there (Rome or Pisa are also options).

We love discovering Italy by car, as it’s the most flexible way to travel the country. As with many other Italian towns, the center of Cortona is an off-limits ZTL zone. Therefore, we parked here (the biggest parking area), and later here (free).

Not traveling by car?

• Organized tour: Many run from larger cities like Florence and include a stop in Cortona, among other places in Tuscany. Book your tour here
• By train: There are direct regional trains between Florence and Rome, stopping at the Camucia Stazione near Cortona. From there, you can either walk or take the local bus into town. Book your train tickets here

Getting around in Cortona: You can easily explore the town on foot.

Where to Stay in Cortona, Italy

Although Cortona makes a perfect day trip in Tuscany, it’s nice to spend the night here, too. We saw that there are many small hotels and bed & breakfasts in the center of town (and remote stays in the countryside!).

Our favorite hotels in Cortona 😴

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Monastero Di Cortona Hotel & Spa

Cortona

Casa Dreosti

Cortona

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Best Time to Visit

We visited at the end of September and loved it! There was still a nice temperature during the day, and in the evenings, we only needed a little jacket. We also didn’t have to make any reservations.

• In summer: Relatively busy, especially during the day.
• Last week of June: Cortona hosts the Tuscan Sun Festival, an annual arts festival that many international stars and artists love to attend.
• Our favorite time: April/May or September/October.