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Arezzo

Piazza Grande – Historic streets of Arezzo loop from Arezzo

Routes

Hiking trails & Routes

Arezzo

Piazza Grande – Historic streets of Arezzo loop from Arezzo

Easy

4.6

(32)

270

hikers

Piazza Grande – Historic streets of Arezzo loop from Arezzo

01:57

6.95km

140m

Hiking

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels. The starting point of the route is right next to a parking lot.

Last updated: July 9, 2026

Waypoints

Start point

Parking

Get Directions

1.26 km

Medici Fortress of Arezzo

Highlight • Historical Site

Jewel of military architecture of the sixteenth century, the Medici Fortress of Arezzo stands on the hill of San Donato.

A terrace overlooking the city, Pratomagno and Alpe di Catenaia. Different historical eras speak in this exceptional sighting point, seat of the Forum for Etruscans and Romans.
Star-shaped plan, adapted to the hill, and five bastions. The current fortress was designed by Antonio da Sangallo the Younger, the architect of the Fortezza da Basso in Florence. At the time, the Grand Duke of Tuscany Cosimo I de' Medici also ruled over Arezzo. Palaces, churches and towers near the work area were demolished. In this way the Florentines, barricading themselves in the fortress, could more easily put down any revolts by the rebels from Arezzo with artillery fire. To fill that void, Il Prato was born, the splendid park that welcomes the Antiques Fair in September.

The bastion of the Thorn, triangular and pointed, looks towards the city. It is the only one not to have the heart shape, typical of Medici defensive structures. A large moat surrounded the complex, which could be entered through three gates. Stone guardian and treasure chest of archaeological treasures, today the Fortress is a place of culture and relaxation. Location of art exhibitions and events and a destination for walks with a breathtaking view of the Casentino. A silent and suggestive gem, on the roof of Arezzo.

source: discoverarezzo.com/place/la-fortezza-medicea-di-arezzo

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2.62 km

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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2.67 km

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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2.76 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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2.86 km

Palazzo della Biblioteca, Poppi

Highlight • Historical Site

Beautiful palace enriched with medieval heralds

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3.40 km

Historic streets of Arezzo

Highlight • Historical Site

The fire brigade does not have an easy job here

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4.53 km

Sculptures at Giardino del Praticino

Highlight • Monument

The Giardino del Praticino is located in front of the “Città di Arezzo” Library. Here are some contemporary sculptures and a public bath.
The most important sculpture is "La Hermana y la Herida", or "The Sister and the Wounded" by Abel Vallmitjana which represents two female figures embracing and with stylized faces, with an anguished and suffering expression.

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5.82 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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Tip by

6.95 km

End point

Parking

Way Types & Surfaces

Way Types

3.28 km

3.06 km

358 m

162 m

< 100 m

Surfaces

4.25 km

1.25 km

1.08 km

285 m

< 100 m

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (310 m)

Lowest point (260 m)

Weather

Today

Monday 24 August

29°C

19°C

73 %

Additional weather tips

Max wind speed: 15.0 km/h

to get more detailed weather forecasts along your route

Comments

June 4, 2025,Rundgang Arezzo

A short, self-guided tour of Arezzo. Visit the Palazzo della Fraternita dei Laici with its bell tower and view over the Piazza Grande, where annual horse races are held, just like in Siena. Stroll through the medieval old town and visit the fortress. The city is even more relaxed than Siena; you hardly notice any other tourists. Overall, it's atmospheric …

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