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A backstage tour through Cortona

| Barbara Kollmann |

How to get here

The picturesque town of Cortona impresses from afar, as it is situated on the slopes of Monte San Egidio, at an altitude of 494 to 650 metres. The town was built on four natural terraces and seems to be illuminated by the sun at all times of the day.

Cortona, its churches and at the top the Fortezza Girifalco

You will love Cortona!

You will be captivated by Cortona with its many labyrinthine alleys full of boutiques, restaurants and shops when you follow the description of my backstage tour. Everything will remind you of life at the Middle Ages and you will be thrilled by the wonderful atmosphere here!

One of the many steep alleys…

Many people who visit Cortona unfortunately are not aware that they miss out on the real beauty of this lively little town because they just walk along the main road to reach the crowded town center. This is why I have prepared a “backstage tour” for you, respectively a short and a slightly longer walk through one of the oldest villages in Italy.

Another shady small passage…

The medieval houses are surrounded by the remains of an Etruscan town wall which still has 6 well-preserved town gates.

This Etruscan town gate is called Porta Montanina

How to get here

The access road continues up the hill winding through beautiful olive groves and vineyards. It goes past villas, farms and monasteries, and before you reach the first parking facilities you will spot the lonely but imponent church of Santa Maria delle Grazie al Calcinaia and its mighty dome. It was built of brick and sandstone in 1484-1515, on the site of a miraculous image of the Madonna which had been found here. Unfortunately, due to the crumbling of the building, hardly any ornamentation on the outside can be seen today. But – thanks to thorough restoration, its beautiful stained glass windows inside, as well as the Madonna painting inserted in the tabernacle above the high altar, are well worth a visit for church lovers.

Please continue for another 2 or 3 bends and you will see the first parking spaces below the city walls.


I recommend to use the parking spaces outside the city walls, as the Centro Storico is closed to non-residents (ZTL – zona traffico limitato).
Another good parking option is the free Parcheggio dello Spirito Santo, from where you can easily reach the historic centre by escalator.

♦︎ Backstage tour – extended version

(approx. 90 min)

☛ Please don’t forget to take some water with you!

I chose Piazza Garibaldi as the starting point of my tour, assuming that you managed to park somewhere along the city wall. Just before you reach the piazza, you can take a quick look at S. Domenico on the right side, a Gothic Roman Catholic church from the 15th century.

From Piazza Garibaldi to Piazza Repubblica

As soon as you can tear yourself away from the incredible view over the Val di Chiana, including Via Lauretana, Lake Trasimeno and even Castiglione del Lago, please follow the flow of people who stroll into the centre.

One of the many impressive views of Cortona

Via Nazionale with its small boutiques, bars and cafés leads to the Piazza della Repubblica with its Town Hall (Palazzo Comunale) and its clock tower. Due to its hillside location, the Palazzo, with locals and tourists milling about on its wide, steep staircase, appears larger and more powerful than it actually is. You might experience a wedding here and the staircase will belong to the bride and groom alone. Or maybe you will hear a band playing music on these stairs. And in the Town Hall you can visit a council chamber from the 13th century.

Via Nazionale

Right next to the Town Hall you can see Palazzo del Popolo from the 14th century (here the Capitano del Popolo once resided) and next to it the Palazzo Passerini, where Pope Leo X used to stay during his visits in 1515. Today, Palazzo Passerini is for sale and parts of it are being offered as holiday flats for well situated guests.

On Saturday mornings, the otherwise cheerful atmosphere on this piazza is dampened by the weekly market, which I cannot recommend because the traders only offer junk.

Speaking of shopping, in the many small stores and boutiques around the centre of Cortona you can often buy original objects made by craftsmen. Also a wide range of typical gastronomic products can be found here – but they are not always cheap…

The Porta Santa Maria – one of the six town gates of Cortona

Now please walk past the Town Hall (Palazzo Comunale) which is on your right and follow Via Roma. You will be magically attracted by the well-preserved Etruscan Porta Santa Maria.

Medieval houses and wooden constructions

From the Porta Santa Maria please walk back a short distance, along Via Roma, until you reach Vicolo Iannelli on the left. This is the “real” Cortona, because here, in this beautiful alley, you can admire medieval houses which still look the same as they did back then.
Do take the second little street on the right, Vicolo Cilli, and then immediately turn left into Via del Gesù. This stone-paved road is also showing you what Cortona looked like in the Meddle Ages; you can see that the upper floors of the houses still consist of wooden constructions.

Piazza Duomo

Once you get to the Piazza del Duomo, again you will have a fantastic panoramic view to the north, and on the left side you can find the Museo Diocesano, which houses very beautiful works of art (unfortunately they are underexposed). And on the right side there is the Cathedral of Santa Maria Assunta, which is built on the remains of an ancient temple. This former parish church from the 11th century is rather unimpressive on the outside, the interior has been remodelled several times over the years, opinions about this cathedral vary.

Climbing to the Basilica Santa Margherita

Our next destination is the Basilica Santa Margherita, dedicated to the Saint of Cortona – she was a very special woman.
(Here is the short version of her story: Saint Margherita of Cortona was born in 1247 near Perugia and lived for several years in Montepulciano. When the man she loved had died – they never got married – she went into custody at the Franciscans in Cortona. Here she lived in great seclusion until she died).

Our way up to the Basilica di Santa Margherita, which is a very impressive church in a very special place, starts at the Piazza del Duomo.
This means you will climb 150 metres in about 20 minutes – let me tell you: it’s worth it! May I recommend to do this particular panoramic walk in the late afternoon, as the magnificent panorama is incredibly beautiful when the sun starts going down. You can see Lake Trasimeno and Monte Amiata from up here. Those who do not want to or cannot take on this strenuous walk may also drive to the Basilica by car.

Basilica Santa Margherita

The mortal remains of Santa Margherita, who was canonised in 1728, are resting in a tomb with a silver reliquary in this church. The interior of the basilica is impressive, great colours, beautiful murals and many historical paintings. The people of Cortona are very attached to this church.

Almost at the top

Now that you have managed to get this far, you might as well continue for another 250 m up to the Fortezza Girifalco. This fortress was built in the 16th century to support the town’s defences, although the site is a defensive structure of a much older origin.

Cosimo I dei Medici was the founder of the fortress and ever since Cortona was an important military town until in 1555 it got subjugated to Siena.
But once again, more beautiful than the historical building is … the panorama over the entire Val di Chiana.

The wide Val di Chiana

And walking down again

Once you are ready to walk all the way down to the heart of Cortona, please keep to the right at the first fork you meet and follow Via Santa Margherita (both ways are called Via Santa Margherita). This path will lead into Via San Niccolo later, which will take you to the small chapel of the same name, San Niccolò. This beautiful church, which can only be reached on foot (residents excluded), is worth seeing, but unfortunately it is not always open. I wish you all the luck!

The little church of S. Cristoforo

(By the way, near San Niccolò you can find the University of Giorgia. I guess I have to mention it, but you’ve probably already noticed that Cortona is predominantly visited by Americans. After Frances Mayes’ bestseller “Under the Tuscan sun” was made into a film in 1996, so many Americans came to Cortona. Lots of them have stayed and so it is not surprising that there is now also a US university in this little town. The above mentioned author still spends at least 5 months a year in Cortona writing books).

Please walk down along Via S. Niccolo until you turn right at the T-junction into Via San Marco; here you take the first left (this alley is also called Via San Marco) and head downhill until you reach Via Giuseppe Maffei. Keep left until the Vicolo del Fontanile branches off to the right, leading you to Via Santa Margherita.

Turn right again into Via Nazionale or Piazza Garibaldi, the starting point of our tour and welcome back.

♦︎ Backstage tour – short version

(approx. 45 min)

Very important: don’t forget water!

The first section up to and including Piazza Duomo is identical for both tours, but the tecnical concept of this blog does not allow text repetitions so I have to ask you to start reading the description of my “Backstage tour extended version” until you reach Piazza Duomo and its Cathedral Santa Maria Assunta.

Piazza della Repubblica and the beautiful clocktower

From the Duomo, the route of the small tour continues as follows:

Please return from Piazza Duomo by crossing Piazza Fraciolini and then turn left into Vicolo del Teatro, which soon bends 90° to the right and ends at a T-junction. Now please turn left briefly into Croce del Travaglio and take the second right at the crossroads: Via Giuseppe Maffei. This road will automatically lead you to the Roman Catholic Church of S. Francesco, which is really worth seeing and was the first Franciscan church built outside Assisi (1245). In 1523, the famous Renaissance painter Luca Signorelli was laid to rest here.

Left and right, and left again…

You should be familiar with the slopes of the alleys in Cortona by now, please continue walking along Via Giuseppe Maffei until you can turn left into Via Moneti (sharp bend). Keep to the right and you will soon be in Via S. Marco, which then splits again (T-junction). Turn right (and you are still in Via S. Marco) until you take Via S. Niccolò on the left, which will lead you to the church of the same name.

Please follow Via S. Niccolo until you reach the next T-junction and turn right into Via San Marco. Take the first road on your left (this street is also called Via San Marco) and walk downhill until you see Via Giuseppe Maffei. Turn right again into Via Nazionale or Piazza Garibaldi, the starting point of our tour. And welcome back!

Now get your reward!

You really deserve a big ice cream after this tour!

You’ll find Gelateria Dolce Vita right at the entrance to the pedestrian zone on the right-hand side (Via Nazionale). It is one of the best in the region.

Another special tip

“Cortona on the move” is an annual, very interesting International Festival for Photography and Video. Please find more informations here:

Fancy an aperitivo?

The bars and cafés change hands so quickly, it’s almost impossible for me to make recommendations.
Personally, I like to go to “Cacio Brillo” on the Piazza Signorelli in the centre of the old town, the staff is friendly and the drinks are good. Here you can relax while enjoying Italy.

Getting hungry?

My personal recommendations include:

♦︎the Osteria del Teatro, Via Giuseppe Maffei, 2 – (closed on Wednesdays)

♦︎il Ristorante Il Cacciatore, Via Roma, 11/13 – glutenfree

♦︎la Trattoria Dardano, Via Dardano, 24

Please check the openings hours.