15 Things to Do in Cortona: A Tuscan Town Worth Visiting in 2023

The beautiful hilltop town of Cortona in the Chiana Valley is an unmissable Tuscan town. With such a long rich history, there are so many things to do in Cortona.

For most of us, we were first introduced to this hilltop town first through the book by Francis Mayes, and then the movie Under the Tuscan Sun. Visiting Cortona Italy is just as dreamy as the movie.

Perched on top of a hill, Cortona Tuscany is an ancient walled town with lively piazzas, endless winding alleyways and many churches. The most sublime views, delicious restaurants and incredible boutique shops are exactly what you’ll find in Cortona.

History buffs, photographers, foodies and romantics – Cortona is a Tuscan town worth visiting!

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#15 Things to Do in Cortona

#1 Soak up the atmosphere at Piazza della Repubblica

The main square is Piazza della Repubblica.

The buildings that sit along the perimeter date back to the 13th century. A well-preserved town hall, clock tower and former palace. 

This is a lively piazza- the very heart of this beautiful town in Tuscany. It’s where you will find the locals constantly coming and going, catching up with one another and stopping in on their favourite shops. 

#2 Walk Via Nazionale

The streets in Cortona are steep. Like, really steep! The steepest I found in all of Tuscany. You will be going up and down as you make your way through the town.

All but one, Via Nazionale. This is the main street and relatively flat. You might even hear locals refer to it as Ruga Piana or flat street.

Via Nazionale links Piazza Garibaldi and Piazza della Repubblica together. So, if you ever get slightly lost, make your way back to Via Nazionale, the set off again.

#3 Get lost in the ancient Medieval streets

One of the best things to do in Cortona is to get lost in the medieval streets.

Seek out the ancient streets of Via Guelfa and Via Ghibellina. The pretty street of Via Iannelli. Via del Gesú, a narrow street with medieval buildings dating back to the 14th century. And lastly, Via Janelli.

It’s a picturesque thoroughfare of 14th-century timber-framed houses. These ancient medieval houses are built of stone and brick, while the jambs, the thresholds and the architraves are exclusively in stone. The upper floors of the house project onto the street and are supported by wooden shelves.

Visiting Cortona Italy was all about the streets for me. If you too love to aimlessly wander and get slightly lost then you’ll love Cortona too.

#4 People watch at Piazza Signorelli

Of all the Cortona things to do, I simply love to do as little as possible. One of the places to do that is in one of the most beautiful squares, Piazza Signorelli.

Named after Luca Signorelli, a famous Renaissance artist, this square features charming cafes, restaurants, and shops. It’s surrounded by wonderful medieval and Renaissance buildings, including the 14th-century Palazzo Comunale.

Not to mention the stunning views of the Tuscan countryside.

Recommend place to people-watch at Piazza Signorelli is Caffe Signorelli.

#5 Visit the Cortona Cathedral

The Cortona Cathedral, or Cathedral of Santa Maria Assunta, sits on Piazza del Duomo at the edge of the fortified wall. It’s a 2:1 deal- you get to see this impressive 15th-century Renaissance church AND admire the panoramic views from this piazza.

#6 Learn the history of early civilizations of the Etruscan period

The Academia Etrusca and Roman Museum of Cortona (MAEC) is housed in the Palazzo Casali. MAEC traces the early beginnings of the ancient people that dates back to 2000 BC.

Wander through the interesting displays of artifacts from the Etruscan and Roman eras.

• Opening Hours: April to October: open daily from 10 am to 7 pm | November to March: open daily from 10 am to 5 pm
•  Cost: € 6.00 audio guide included

In addition to the museum, you can visit the Archaeological Park Of Sodo to look at the Etruscan Tombs found at the foot of Cortona. Etruscan tombs date back to the 3rd century BC, as well as a Meloni (a type of mound) from the Archaic period can be visited.

• Opening hours: Open daily from 10 am to 6 pm (closed from 2 pm to 3 pm)
• Cost: Parking free | discount if show ticket from MAEC
• Location: Località Sodo | 4 km
• Distance: 4 km walk from Cortona

#7 Admire the views from Piazza Garibaldi

One of the best views can be found on this piazza, also known as Belvedere di Cortona. Going to this scenic viewpoint is considered one of the unmissable things to do in Cortona.

Every hilltop town in Tuscany affords amazing views. And, Cortona’s views are incredible.  Of course, there are many piazzas and alleyways throughout Cortona where you can do this, but this one is one of the best.

This is the spot where you can gaze upon the view of the Val di Chiana and Lake Trasimeno. 

#8 Visit the Church of San Francesco

The Church of San Francesco is considered one of the earliest Franciscan churches, dating back to 1245.

It’s not only a beautiful Renaissance church, but it also houses important works of art, including frescoes by the famous Italian painter, Pietro Lorenzetti.

It’s also famous for its association with St. Francis of Assisi, who is said to have preached in the church in the 13th century.

#9 Go to the Diocesan Museum

The small museum is home to a superb art collection. Telling the town’s history from the 2nd century to the 18th century through art.

Both art and history lovers will want to add this to their things to do in Cortona. The famous paintings include Madonna and Child, Annunciation, Crucifix and others.

• Opening hours: April to October – open daily from 10:30 am to 6:30 pm and November to March – opening daily from 10 am to 5 pm
• Cost: € 6.00 audio guide included

#10 Go shopping

Have you ever had that “Oh I should have bought that” moment? I did, and it was in Cortona. It was a biker-style leather jacket in deep red that I still think of today! That’s all to say, the shopping in Cortona is surprisingly rather good! Like, really good.

Little artisan shops can be found throughout every little street. Ceramics, artwork, knitwear, leather, handmade paper and a hat shop. If you love to shop, plan on spending a bit more time in this beautiful town for the shops alone.

One of the oldest shops is a wine store called Enoteca Molesini from 1937. Visiting this multi-generational family shop is a must!

#11 Take a guided tour or a cooking class

If you love experiences when travelling as much as I do, you’re going to want to check these out. Adding a guided tour or activity always makes for an extra special trip.

• Walk with a local and learn all about the secrets and history of Cortona Tuscany. This 2-hour walking tour of the historic centre will bring you to all of the important landmarks. Learn more about this 5-star rated tour here.
• Get into the kitchen and cook with a local. You’ll make learn how to make pizza, pasta and focaccia and then enjoy the meal together. Learn more about this 5-star rated tour here.

#12 Go see the Girifalco Fortress and church of Santa Margherita

The Girifalco Fortress overlooking Cortona is thought to date back to the 5th or 6th century, even though on record the first mention of the fortress was in 1258. The fortress walls connect to the town walls and create a pentagonal-shaped, internal courtyard.

Combine your visit here with the shrine dedicated to Santa Margherita, a neo-gothic basilica. Both offer amazing favourite viewpoints for sweeping views of the Chiana valley.

• Opening hours: Open daily at 10 am and depending on the season it closes from 6 pm to 8 pm
• Cost: €5.00 | church is free
• Location: Via di Fortezza | Drive and park (less than 10 minutes) or walk in 15 minutes

#13 Visit the Monastery of Saint Francis “Le Celle”

The village of Le Celle is where you’ll find the Monastery of Celle, a sacred building offering a gorgeous view of the Chiana Valley.

This was the first monastery built by St. Francis of Assisi in 1211. It’s believed that he dictated his Testament here in 1226, just a few months before his death. You can visit his cell featuring his personal objects.

• Opening Hours: Open daily from 7 am to 7 pm
• Cost: Free
• Location: Strada dei Cappuccini 1 Cortona, 5 minutes by car 2 km or on foot about 30 minutes

#14 Church of Santa Maria delle Grazie

Depending on the direction you go or leave Cortona there are bound to be two churches that catch your eye. It is the most incredible site as you drive on the winding road leading you to the hilltop town.

The Santa Maria delle Grazie al Calcinaio, also called the Madonna del Calcinaio was my favourite. This church was built in 1513 and is one of the most architecturally significant Renaissance churches in all of Tuscany.

On the opposite side of Cortona is where you’ll find a similar-looking church called the Church of Santa Maria Nuova. This one can be seen from the viewpoints in Cortona.

#15 Villa Bramasole from Under the Tuscan Sun

I fell in love with Cortona even before even visiting here. It got my attention with the release of Under the Tuscan Sun, first the book by Francis Mayes, and then the movie. There is an actual Villa Bramasole! Well, there are two where the movie was filmed and the other is the real villa Francis Mayes bought.

The villa can be reached by foot, starting from the public gardens in Cortona “Parterre.” It’s about a 4 km walk along a somewhat busy road which is a better option than driving, as there is no way to pull over if you want to see it better.

This is a private home, and really you can’t see much from the road. The gate of course, but due to the mass amount of tourists that flock here there are high hedges around the perimeter.

Cortona Restaurants

Cortona has some great restaurants to try from tiny cafes to trattorias to Michelin star. Some of the local specialties you’ll want to look for on the menu of these Cortona restaurants are:

• Ribollita, a typical Tuscan bread soup (vegetarian)
• Pappa col pomodoro, a delicious Tuscan tomato soup (vegetarian)
• Tagliata, or beef
• Cantucci col vin santo – a hard almond biscuit with sweet wine (for dipping)

Here are some recommended Cortona restaurants:

• For the best gelato: Gelateria Snoopy 
• The oldest and best wine bar: Enoteca Molesini 
• For best coffee:  Café Tuscher
• Al fresco dining: La Loggetta
• And, to enjoy a long lunch or dinner at Il Facloniere, a 17th-century villa surrounded by cypresses, olive trees and vineyards. This Michelin-starred restaurant serves local hearty Tuscan dishes as well as the estate’s own wine. Be sure to request a table on the outdoor terrace where you will be awarded with a gorgeous view of Cortona and the valley.

Where to Stay in Cortona

Cortona can easily be seen in one day, but if you would like to make Cortona your base, this ancient town offers a wide range of accommodations, both in town and close to it. I’ve even custom created a list of the dreamy places to stay in Cortona Italy. In addition, here are some of the best accommodations in Cortona.

• Hotel in the old town: Hotel San Michele is located inside one of the oldest buildings of Cortona, the ancient Baldelli Palace. Updated rooms in the 15th-century palace overlook the terra cotta roof tiles and the countryside views beyond.  
• Luxury countryside villa: Relais La Corte dei Papi offers luxurious accommodation in a tranquil, romantic setting just 10 minutes from Cortona. This 18th-century villa with a pool also offers a fine-dining restaurant
• Sunflower Beams – a 2-bedroom self-contained apartment located in Cortona’s historic centre. This attractive apartment blends rustic charm with modern comforts to create a memorable, relaxing stay.
• Apartment in the historic town centre: Cortona Suite is on the second floor of a 15th-century building overlooking Piazza Signorelli square. A light breakfast is available for your stay.  
• Or, explore other properties using Booking.com

Day Trips from Cortona Italy

Whether you decide to make Pienza your base to explore other nearby towns or are still looking for ideas, consider these other beautiful towns that are 60 km or less from Cortona.

• Arezzo to Cortona – 30 km
• Montepulciano to Cortona – 31 km
• Montefollonico to Cortona – 33 km
• Torrita di Siena to Cortona – 33 km
• Lucignano to Cortona – 33 km
• Monticchiello to Cortona – 40 km
• Pienza to Cortona – 50 km
• San Quirico d’Orcia to Cortona 59 km

Italy Travel Resources

To help with your Tuscany trip inspiration and planning, check out some of my other articles, as well as other cities and guides in Italy.

Tuscany

• 19 Best Tuscan Towns to Visit
• Guide to Florence – top things to do
• Guide to Siena – how to spend one day
• Guide to Pienza – top things to do

Italy

• Venice vs Florence: which city is better?
• Guide to Rome
• 18 Best UNESCO World Heritage Sites in Italy
• Things to you need to know before you go to Italy

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FAQ

As a holidaymaker

There’s a saying in Italian, Passeggiata, which means to stroll in a town looking good. The chicer the town, the chicer the passeggiata. Cortona is definitely the town to do this in.

Of all the Tuscan towns, this one felt and looked a little bit different. The winding alleyways and buildings were a bit more elegant. I fell in love with the pale blue-grey stone buildings; as well as, the finer shops and restaurants that you will find here.

There are so many things to do in Cortona Italy that you’ll need more time than in the other smaller villages. Visiting Cortona Italy is a definite YES!