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Italy

Tuscany

Arezzo

Historic streets of Arezzo – Piazza Grande loop from Arezzo

Routes

Running trails & routes

Italy

Tuscany

Arezzo

Historic streets of Arezzo – Piazza Grande loop from Arezzo

Hard

runners

Historic streets of Arezzo – Piazza Grande loop from Arezzo

06:05

44.7km

1,600m

Running

Hard run. Very good fitness required. Mostly accessible paths. Some sure footedness required. The starting point of the route is accessible with public transport.

Last updated: April 8, 2026

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Start point

Train Station

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355 m

Guido Monaco Square

Highlight • Monument

The square is circular in shape, with a diameter of 100 m, dating back to the 19th century, located at the crossroads of three very important roads: via Guido Monaco (1870), via Petrarca and via Roma. In the center of the square is the monument, by Salvino Salvini (1882), to Guido Monaco (or Guido D'Arezzo), the creator of modern musical notation and the tetagram.

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793 m

Historic streets of Arezzo

Highlight • Historical Site

The fire brigade does not have an easy job here

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925 m

Santa Maria della Pieve, Arezzo

Highlight • Religious Site

The facade in Corso Italia, the apse in Piazza Grande. The Pieve di Santa Maria Assunta in Arezzo is the link between two of the most important and lived-in places in the city. Built starting from the year 1000, this Romanesque church presents itself in all its magnificence with a façade with three portals. We all immediately look at the Pieve with our noses turned up, because we cannot fail to be fascinated by its bell tower, known as the "hundred hole" for the mullioned windows, once ten on each side, which make it unique.

At the back of the church is the large semicircular apse: small single-lancet windows illuminate the interior of the crypt where the 1346 reliquary bust in gilded silver is kept with the relics of San Donato Vescovo, the patron saint of Arezzo.

All you need to do is cross its threshold to admire, inside, a masterpiece of fourteenth-century painting: the Polyptych with the Virgin and Child and Saints John the Evangelist, Donato, John the Baptist and Matthew commissioned from Pietro Lorenzetti in 1320, not to mention the beautiful Chapel of the SS. Sacramento, where delicate pastel-coloured frescoes by the master Luigi Ademollo frame a sweet fifteenth-century statue of the Madonna in polychrome terracotta.

source: discoverarezzo.com/place/pieve-di-santa-maria-assunta

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970 m

Piazza Grande

Highlight • Historical Site

Arezzo is a city perched on a hill surrounded by four valleys. Its origins are ancient, dating back to the Etruscan and Roman eras, and it boasts numerous historical and artistic monuments, thanks in part to illustrious figures born here, such as Vasari and Piero della Francesca. It is an elegant and lively city, an ideal starting point for a bike tour of Tuscany.

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1.06 km

Vasari Loggias

Highlight • Monument

This long loggia was commissioned to Giorgio Vasari by Cosimo I De' Medici, when Arezzo was still under the dominion of the Florentine Republic. Today it crowns the northern part of the square and under its large loggia it houses classy shops and restaurants.

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1.30 km

Park of the Medici Fortress "The Lawn"

Highlight • Natural

Parco del Prato, between the Duomo and the Medici Fortress, is Arezzo's great green balcony. The city's oldest public park, its open lawns and tree-lined avenues invite you to slow down and enjoy one of the most beautiful views of the historic center and the surrounding hills.

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1.74 km

Piazza Grande of Arezzo

Highlight • Historical Site

On this cold January day, made pleasant by full sun and the absence of that humidity that never leaves the Valdarno, we took a nice ninety-kilometer ride to Arezzo.
The city is located on the Cassia, on a hill at the intersection with four valleys (the Valdarno is precisely one of these) has always played an important and prominent role in Tuscan history and its rich monuments, churches and museums to visit, are today the legacy.
The friends who left Montevarchi joined me in Loro Ciuffenna (one of the most beautiful villages in Italy) and from here we continued in the direction of the provincial capital along the Setteponti, the ancient Etruscan-Roman road.

ᴀʟᴛʀᴇ ɪɴꜰᴏ ᴛʀᴀᴛᴛᴇ ᴅᴀ ᴇxᴩᴇᴅɪᴀ
Not far from Florence and Siena, Arezzo is an extraordinarily ancient city, older than Alexandria in Egypt. It was one of the major Etruscan centers and subsequently became a Roman city of strategic importance, as well as a center of flourishing economic activities. Today museums, theaters and monuments speak to the visitor, reviving past myths and glories in his imagination. The advanced network of accommodation facilities, on the other hand, combined with a unique local friendliness, make travel offers to Arezzo always attractive and advantageous.

The main attraction of the city is certainly the Basilica of San Francesco, located in the city center. Inside the Basilica there is the famous Bacci Chapel which preserves the wonderful cycle of frescoes of the Legend of the True Cross, a masterpiece of Renaissance painting by Piero della Francesca. Continuing along Corso Italia, we arrive at the Pieve di Santa Maria, characterized by an interesting Romanesque façade and by its bell tower, 59 meters high and also called "with a hundred holes", the most precious building of all the Tuscan Romanesque. Inside there is a polyptych by Pietro Lorenzetti, the Madonna, Saints and a wooden cross by Margarito. Of the ancient facade you can admire the extraordinary medieval cycle depicting the twelve months of the year.

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