Siena Historic Centre Guided Walking Tour

siena walking tour
  • Basilica of San Domenico

  • Siena Cathedral

  • Panoramic view of the historic centre

  • Medieval alleys

  • Piazza del Campo

  • Medieval palaces of Siena

Duration of the tour: 3 hours
Difficulty: medium
Suitable for children: yes
Accessibility for different ables: yes
Difference in level: 70 metres

Further information at the bottom 

A tour for those who come to Siena for the first time

Siena guided walking tour is an itinerary endowing you to discover all the beauty of this wonderful city which, thanks to the exceptional state of repair of its medieval buildings and unique traditions, has been recognized as a UNESCO heritage city. Already documented in Roman times, Siena developed in the Middle Ages thanks to the trades on the Via Francigena, the pilgrims’ path that, from northern Europe, allowed to set off on the journey to Rome. Thanks to its enterprising class of merchants, the town became one of the most important commercial powers of the Italian peninsula and rivalled with the nearby Florence.

We will begin the Siena walking tour starting from the San Domenico Square, the starting point of the historic centre which is where we already find the majestic Basilica of San Domenico, the largest religious building in Siena after the Cathedral. By a visit of its interior, we will go over some events of Saint Catherine of Siena’s life, a mystic woman of the fourteenth-century who was particularly bound to this church and to the Dominican Order which, even today, spiritually and materially looks after of the building. In a chapel dedicated to the saint – beautifully decorated with frescoes by Sodoma – it is where you can see an important relic of Santa Caterina. We will then admire some fifteenth-century masterpieces of Sienese art here preserved, such as the paintings by Francesco di Giorgio Martini and Matteo di Giovanni.


View of Fontebranda quarter

On the route of the Via Francigena

Leaving the church, we will look out to a panoramic point from where you can enjoy a spectacular view over almost the entire historic centre – characterized by the typical orange and pink shades of the local cotto (the terracotta) – on which, for the whiteness of its white marble, the bulk of the Cathedral stands out, as it was built on one of the highest hills of the town.

Once we have begun the itinerary through the picturesque streets of the centre, we see Palazzo Salimbeni, an outstanding building in the city, once owned to the Salimbeni family of the same name, which in the fourteenth-century was among the most powerful in the Republic of Siena. The palace is now the historic seat of Monte dei Paschi, one of the oldest banks in the world.

Siena Cathedral and its masterpieces

Going down again a part of the ancient Via Francigena route, we reach the San Cristoforo Church which, with its adjacent xenodochium, is a significant example preserved in Siena as an accommodation facility for pilgrims who passed through the town. In the square where the San Cristoforo church stands it is also where we will find Palazzo Tolomei, an unmatched refined example of the thirteenth-century palaces of Siena, wanted by the family of the same name that, in the mid-thirteenth-century, was the protagonist in the fierce struggles between Guelphs and Ghibellines. Once we arrive in front of the Loggia della Mercanzia, we will discover why the statues depicting the protectors of Siena are all ‘threateningly’ looking towards the north, in the direction of Florence … We will then move to via di Diacceto to enjoy another breathtaking sight of the city, having the opportunity to appreciate in particular the Basilica of San Domenico – the one previously visited – and the suggestive Fontebranda quarter: your desire to capture this wonderful view in a photographic shot will be irresistible. Continuing through the enchanting medieval alleys, you will be speechless when, suddenly, we will have arrived in front of the Duomo. Built between the twelfth and fourteenth centuries, the Siena Cathedral is one of the most admirable examples of Gothic architecture in Italy, especially for its façade, built at the end of the thirteenth-century on a design by Giovanni Pisano. On request, I will accompany you on a visit to the interior which, besides being sumptuously decorated, preserves some masterpieces of the most famous Italian masters: in fact, there are works by Donatello, by Pintoricchio, the latter author of the Renaissance frescoes of the Piccolomini Library – to whose drawings Raphael also collaborated; next to the Library is the altar – also by Piccolomini – where Michelangelo’s youthful sculptures are kept. If after having seen these wonders you’d already think that absolutely worth visiting the Duomo, you cannot therefore believe my words when I will tell you that there are other masterpieces to admire, such as the sculptures by the great Roman artist Gian Lorenzo Bernini – preserved inside the Cappella del Voto – and the pulpit by Nicola Pisano, a pivotal work of all Italian medieval art.

siena walking tour

Characteristic alley of Siena historic centre

Siena Cathedral

The façade of the Siena Cathedral

The Via di Città and the Accademia Chigiana

Leaving the Duomo, we continue our Siena guided walking tour towards Piazza Postierla to admire other monuments of the city, such as the case torri (tower-houses), an important architectural testimony of medieval culture. Arriving in this square, you will see a detail that you have already noticed in other points of our route: the numerous presence of Lupe Capitoline (Roman She-wolves)… the reason for which are so many the figures featuring the roman symbol in Siena is a thing that we will find out along the way. We then move on by Via di Città, the street that once led to the ancient urban area of ​​Siena from the “Campo” area; walking on this historic path, the evocative presence of the artisan shops, as well as that of aristocratic palaces, give to the street a look of refined elegance will certainly draw your attention. Heading towards Piazza del Campo, we pass in front of Palazzo Chigi-Saracini, home of the Accademia Chigiana, one of the most important institutions in the world music scene, founded in 1932 by Count Guido Chigi Saracini.

The enchanting Piazza del Campo

Passing through the suggestive Chiasso del Bargello, we will conclude our Siena guided walking tour in the famous Piazza del Campo, the authentic core of the town and one of the most ancient European squares, where every year the historic Palio race is held. When you arrive inside this square, you will be completely enraptured by the beauty of this space, surrounded by medieval buildings. Above all, what will strike you about the square is its particular trapezoidal shape and the division of the inside into nine segments; we will discover the important symbolism of this issue and how it is related to the history of Siena. In the background of the square stands the elegant Palazzo del Comune – better known as Palazzo Pubblico – now houses the Civic museum where great masterpieces of art are preserved, such as the extraordinary frescoes of the Buon Governo by Ambrogio Lorenzetti, the best-known medieval cycle of profane-themed paintings.

If you are an art lover, or are curious to learn more about Siena, I will accompany you on a visit to one of the important city museums, such as the Museo dell’Opera del Duomo (where the famous Duccio di Buoninsegna’s Maestà is kept), the National Pinacoteca (the gallery holding the largest world collection of gold foiled paintings), or the Santa Maria della Scala Complex (one of the oldest and largest hospitals in medieval Europe, in this day converted into a suggestive museum which hides an underground quarter of the town). Along the way, there will be suggestions on the shops where you can taste the typical Sienese sweets, as well as advice on the best restaurants and Trattorias where you can taste the typical local dishes, prepared according to tradition.

The Pulpit by Nicola Pisano, Siena Cathedral

piazza del campo

Piazza del Campo

This tour can also be booked in combination with the other available tours on Siena and Florence, which can be consulted in the Menu.

The guide is not a tourist agency; therefore he cannot book external services (e.g. lunches or tastings), but only provide information about external services. The cost of the entrance ticket to the Cathedral or to the other museums (in the event you want to visit them) is not included in the tour rate. The access to the Basilica of San Domenico is for free.

The guide does not provide transportation service. For organized groups/squadrons by tourist coach, there are drop-off/drop-on points for passengers in the urban centre of Siena (click here to view the points). Tourist coaches are subject to the payment of a checkpoint (further information by clicking here). In the presence of different ables people, or people with ambulation difficulties, the sections of the route having the biggest difference in level, will be avoided.

To get further information, to book the tour or to get the contact of a licensed driver providing private transfer service, please write to: