What to do in Montepulciano

Itineraries in the Historic Centre

Itinerary 1 – GREEN
Approx. 1 km – Medium difficulty
From Porta al Prato to Piazza Grande
From the Pro Loco Tourist Office (Piazza Don Minzoni), you take Viale Sangallo, enter from Porta al Prato and continue along Via di Gracciano nel Corso, Piazza delle Erbe, Via di Voltaia and Via dell’Opio, reaching Piazza Grande from Via del Teatro.
This first itinerary leads you through the Historic Centre starting from the main gate, located at the foot of the town, visiting palaces, wine cellars and craft shops, walking along the main street for about one kilometre and accessing Piazza Grande from Via del Teatro. This piazza is the setting of many activities; it is surrounded by historic buildings, including the Cathedral, and monumental wine cellars.

Itinerary 2 – BLUE
1,200 metres – Medium-high difficulty
From Car Park 5 (Bus Station) to Piazza Michelozzo (then Piazza Grande)
From Car Park 5Bus Station, you walk along Via delle Lettere, Via di Gozzano and Via di Borgo Buio to reach the main street close to Piazza Michelozzo and then continue as per Itinerary 1 (green).
If you are travelling by camper van or tourist bus, we suggest accessing the town from Via di Gozzano, as an alternative to the main street, so as to go along Via di Borgo Buio and walk a shorter distance.

Itinerary 3 – ORANGE
300 metres – Medium difficulty
From Via dell’Oriolo to Piazza Grande
FromVia dell’Oriolo, P7, outside Porta delle Farine (often used as tourist bus park), you take Via delle Farine, Via del Poliziano and Via di San Donato to reach Piazza Grande.
Bus Park 7 for tourist buses lets groups reach the upper part of the Historic Centre and the Piazza more quickly, going up Via delle Farine or the stairway leading to Via dell’Opio.
From Piazzetta di Cagnano, you have two options to reach the Piazza: Via del Teatro or Via del Poliziano (the latter is lined with monumental buildings, like the Church of St. Mary, and historical wine cellars).

Itinerary 4 – PINK
1 km – Low difficulty

From Piazza Grande to Piazza delle Erbe
From Piazza Grande you go down along Via Ricci and then Via del Poggiolo to reach Piazza delle Erbe. From here, you continue going down towards Porta al Prato. Otherwise, you do up the main street (see the green itinerary) to return to Piazza Grande, in which case the total distance will be 1,800 metres.
This itinerary can be chosen by those who reach the Piazza from Via del Teatro or Via del Poliziano to return to Porta al Prato.
Via Ricci runs along a very important part of the town where are located, among others, the Crociani Civic Museum and Picture Gallery, Palazzo Ricci, the Library and several shops.
Going down Via Ricci, we recommend a stop in Piazza San Francesco, an awesome panoramic viewpoint.

Itinerary 5 – RED
650 metres – Medium difficulty
From Car Park 8 to Piazza Grande
You go along a part outside the Historic Centre, taking a panoramic route that lets you admire the Temple of San Biagio from above and take a view of the small village of Montefollonico.
This itinerary leads you quickly to Piazza Grande, for a short but significant visit to the monumental heart of Montepulciano.

Itinerary 6 – YELLOW
1 km – No difficulty
From Piazza Grande to Tempio di San Biagio
From the Piazza, walking along Via Ricci and Via di San Biagio, you reach the Temple of San Biagio (about 1 km).
It is a panoramic itinerary leading to this beautiful Renaissance church located outside the historic centre.
From here it is then possible to take the shuttle bus to return to the bus station or to the various car parks outside the town walls.


    With about three hours at your disposal, you can have a taster of Montepulciano, giving the town a quick glance. The same way an aperitif whets your appetite for lunch or dinner, a brief visit could arouse your curiosity and leave you filled with the desire to come back and visit for longer, taking in everything beautiful and good that the town has to offer. The detailed explanation of the “coloured” or numbered itineraries can be found in the section “itineraries in the Historical Town Centre”.


    For a visit of about three hours, we suggest a walking tour which can offer an overall view of the Old Town, taking in the main monuments and also visiting at least one of the monumental cellars, which will be no less interesting. Remember that Montepulciano is one of the only towns in the world to have underground cellars, and not just in the countryside.

    You can start your tour at Porta al Prato, the main entrance in the lower part of the town. It can be reached by car, using one of the carparks in the area below the Porta (Gate), or by bus, stopping to let passengers off in Piazza S. Agnese.

    Once through the Gate, you find yourself in the main street, Via di Gracciano, a splendid example of a combination between the preservation of history and its use in a natural shopping centre.

    Here you will find the first monuments and historical buildings: the Marzocco Column, with the lion, symbol of Florence; Palazzo Avignonesi; Palazzo Bucelli, with its exterior foundation set with Etruscan and Roman inscriptions and urns; the Church of S. Agostino, the splendid façade of which bears the Gothic and Neo-classical symbolic styles that characterise the town; and the characteristic and particular Pulcinella’s Tower. From here, the climb begins to Via di Voltaia, with Caffè Poliziano, one of Italy’s historical cafés, and Palazzo Cervini.

    To make the walk even more pleasant, you can stop off in one of the many little squares that open up before, maybe enjoying some excellent artisan ice cream or, if you prefer something savoury, tasting the local cured meats and cheeses. We also recommend that you visit one of the splendid monumental underground cellars of the noble buildings, to taste one of Italy’s internationally famed products of excellence: Vino Nobile di Montepulciano.

    Continuing along the road, just before coming to the main square, you will see Porta delle Farine on the left, with its beautiful view over Val di Chiana. Nearby is the house where Agnolo Poliziano was born. Walking up Via del Teatro, you will arrive in Piazza Grande, with its elegant perimeter of buildings and monuments: the Cathedral of Santa Maria Assunta, Palazzo Comunale (Town Hall), Palazzo Nobili Tarugi and Palazzo Contucci. The square is used to host events and performances all summer long; the parvis of the Cathedral is a very large and extremely beautiful stage. The shows of Cantiere Internazionale d’arte are staged here (in July), as are the popular theatre of the Bruscello (August), the final stages of the Bravìo delle Botti (last Sunday in August), and the characteristic Christmas market (November/December).

    During the whole summer season, on the other hand, it is possible to visit the tower of Palazzo Comunale, open from March to November. The building is one of the symbols of Montepulciano and its terrace offers an unforgettable view of the town. From the top of the tower you can look out over the surrounding panorama, with a 360° view. No visit, however short, would be complete without tasting local specialities and no-miles seasonal products in one of the typical restaurants.


    A whole day allows you to get to know the town a bit better, making a small diversion outside the walls to visit the Temple of San Biagio (visit with the ticket), spend time wandering around the Crociani Civic Museum-Picture Gallery and taking the time to look inside a couple of monumental cellars. The detailed explanation of the “coloured” or numbered itineraries can be found in the section “itineraries in the Historical Town Centre”.


    For this walking tour, we recommend entering the town through Porta al Prato, following the same directions given for ROUTE 1 as far as Piazza Grande.

    From the square, walk down past the medieval Palazzo del Capitano, arriving in Via Ricci, seat of the building of the same name (Palazzo Ricci) and its monumental cellar.

    On the right is Palazzo Neri Orselli, with the original Gothic façade, home to the Crociani Picture Gallery and Civic Museum. We strongly recommend visiting this museum, because it tells you about the origins of Montepulciano and its artistic progress over the centuries, in a fascinating itinerary which, starting from the town’s Etruscan and Roman origins, comprises medieval ecclesiastic works and Renaissance paintings, as well as the 17th and 18th century portrait collection. There is also a very interesting section of 16th century terracotta works by the Della Robbia sculptors.

    The creators of works on display include famous names like Margaritone d’Arezzo (Saint Francis, 13th century), Benvenuto di Giovanni (Nativity, panel painting), Antonio Bazzi, known as Sodoma (Holy Family with Saint Giovannino) and Andrea della Robbia.

    There are also two recently attributed works: Saint Agnese, on canvas, by Domenico Beccafumi; and a portrait of a gentleman, attributed to Caravaggio.


    From Via Ricci, leaving behind the Old Town, you can walk down Via di San Biagio to the Temple of San Biagio (visit with the ticket). Example of Renaissance elegance and style, this big church was designed by Antonio da Sangallo the Elder, and is still one of the town’s symbols today.

    The view from the Church is unique, with the hills of Val d’Orcia, the little village of Montefollonico and Val di Chiana.

    The area of San Biagio is also a perfect starting point for setting out on other walking or cycling routes.

    From the Church of San Biagio, you can easily return to the town centre, using the urban shuttle bus service. The service runs once an hour and stops in front of the Church (there is no service on Sunday mornings). If you want to walk to the Sant’Agnese area, you can take Via di Canneto. The route is about 2 km long and is not particularly difficult, apart from the last short uphill stretch.