Touring Tuscan Towns – Cortona

Cortona, is a beautiful Tuscan town. 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 put Cortona Italy on the map. 

This Tuscan town lies in the province of Arezzo, in the Chiana Valley in southern Tuscany. Cortona to Florence is a 90-minute drive. Check out our Guide about Florence here. 

Perched on top of a hill, Cortona is an ancient walled town with lively piazzas, endless winding alleyways and many churches. This is your guide to the best things to do in Cortona Italy.  

Top Things to Do in Cortona

PIAZZA DELLA REPUBBLICA

The main square in Cortona is Piazza della Repubblica. The buildings that sit along the perimeter date back to the 13th century. Here you will see significant attractions that include a well-preserved town hall, clock tower and former palace. 

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

THE STREETS OF CORTONA

The streets in Cortona are steep. You will be going up and down as you make your way through the town. All but one, the main Via Nazionale, which links Piazza Garibaldi and Piazza della Repubblica together. You might hear locals refer to it as Ruga Piana or flat street. Seek out the ancient streets of Via Guelfa and Via Ghibellina. 

Another top attraction is to find 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.

THE ETRUSCAN WALLS

Cortona is believed to have been a powerful Etruscan town during the period of 400-600 BC. Then in the 13^th century it became a city state with its own currency. It was owned by the Medici family and remained under their rule until 1737. Following the Italian Wars of Independence, Cortona became part of the Kingdom of Italy.

The Etruscan walls are incorporated into the medieval walls that surround the historic center. Inside the walls, you can wander the narrow medieval streets often getting glimpses of the wonderful views of the valley below.

CHURCHES IN CORTONA

Even in a small town, there are a lot of churches in Cortona. All playing a significant role in history makes each of them interesting to visit. My favourite, pictured above, can be found on the outskirts of Cortona. The Santa Maria delle Grazie al Calcinaio, also called the Madonna del Calcinaio was built in 1513 and is one of the most architecturally important Renaissance churches in all of Tuscany. Here are others to visit:

• San Francesco is considered one of the earliest Franciscan churches (1245)
• Cathedral of Santa Maria Assunta, a Renaissance structure (15th century)
• Church of San Doménico (15th century)
• Sanctuary of Santa Margherita, a pilgrimage church (19th century)

MUSEUMS IN CORTONA

The best way to learn about the interesting history of Cortona is to visit its museums. Here are the top ones to visit:

1. The small Museo Diocesano, or Diocesan Museum across the piazza features a superb art collection. It depicts the town’s history from the 3rd century to the 18th century. 
2. Wander the fascinating Museo Etruscan Museum displaying artifacts from the Etruscan and Roman eras. 
3. Take a look at the Etruscan Tombs found at the foot of the town. Here you will see the Etruscan tombs dating back to the 3rd century BC.                             

GIRIFALCO FORTRESS

The Girifalco Fortress overlooking Cortona dates back to 5th or 6th century. The fortress walls connect to the town walls and create a pentagonal-shaped, internal courtyard. It is one of the favourite viewpoints for admiring the surrounding Tuscan landscape.

VIEWS FROM CORTONA

Due to being perched on a hill, Cortona’s views are incredible.  There are a few piazzas and alleyways where you can gaze upon the view of the Val di Chiana and Lake Trasimeno. 

Best Places to Stay in Cortona

Cortona can easily be seen in one day, but if you would like to make Cortona your home base, this ancient town offers a wide range of accommodations, both in town and close to it. 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 fine dining restaurant
• Agriturismo in a great location: Agriturismo Pagliai is a 15th century estate that produces its own olive oil and vegetables. Stay in a rustic suite or individual apartments.
• Apartment in the historic town centre: Cortona Suite is a 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

Here are some best places to eat in Cortona:

• Gelato: Gelateria Snoopy 
• Wine bar: Enoteca Molesini 
• Coffee:  Café Tuscher
• Alfresco dining: La Loggetta

Best Day Trips from Cortona

If you’ve decided to make Cortona your home base, here are some popular day trips you might wish to take. 

• Villa Bramasole – tourists flock to the villa that was featured in Under the Tuscan Sun. And there are two, one where the movie was filmed and the other is the real villa Francis Mayes bought. Both are within walking distance from Cortona
• Pienza – a 15th century Renaissance town designated a UNESCO World Heritage Site is a 50-minute drive. Check out our Guide of Pienza here. 
• Montalcino, Montepulciano, and Arezzo – are all notable hilltop towns in under an hour’s drive from Cortona. Check out our Guide of these Tuscan towns here.
• Siena – a medieval city that is known for its 13th century Piazza del Campo, considered to be one of Europe’s greatest medieval squares. Siena to Cortona is an hour’s drive. Check out our Guide to Siena here. 

As a holidaymaker…

There is 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 we toured, 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. Cortona is a definite must experience town when in Tuscany.