Montepulciano is the ideal Tuscan medieval village to discover the Val di Chiana and the Val d’Orcia.
Here are 5 things to see in Montepulciano and actually many more to do!

We tell you what to do if you only have half a day to spend in Montepulciano: where to eat, what to do, where to taste wine, what to see in the historic center… and also a bit of history because there is so much to tell! Even if it rains there are many things to do.

First 5 things to see… and then tourist information on Montepulciano. At the bottom of this article I will talk about a special shop. Let’s get started right away !!

What to see in Montepulciano

As promised, a very brief history because the city of Montepulciano has historically played a particular role in Tuscany.
Montepulciano, with Etruscan origins from the 4th century BC. it is now famous for the Nobile di Montepulciano wine.

Located 30 minutes from Relais Osteria dell’Orcia and 15 minutes from Pienza, Montepulciano has been, in the past, in the midst of the territorial war between Siena and Florence. Historical trading square and fantastic fortress thanks to its dominant position on the surrounding area, today it offers a journey through Tuscan history. There is plenty to do in Montepulciano, beautiful panoramas and nice shops of local art and products!

Piazza Grande of Montepulciano

piazza grande montepulciano

Piazza Grande is the gathering point for local people of Montepulciano. At the vibrant heart of the city takes place all the main events, starting from the Bravio delle Botti, passing through the annual International Art Shipyard and ending with the Christmas markets. Just to name a few.

All around the square we find some of the most beautiful buildings in Montepulciano. But also the Cathedral, an almost copy of the Palazzo della Signoria in Florence. Also worth seeing is the well with the Medici coat of arms designed by Sangallo.

Designed by the best Renaissance architects, such as Antonio da Sangallo, Michelozzo Michelozzi and Ippolito Scalza, the buildings in Piazza Grande are truly wonderful!

Did you know?

Piazza Grande, considered the “Pearl of the sixteenth century“, has hosted numerous international productions! Such as the TV series “Medici – Master of Florence”. But as well”Moon Light” of the famous serie Twilight. To name only those two.

San Biagio Church

Chiesa di san biagio

This imposing Catholic church of the diocese of Montepulciano-Chiusi-Pienza is also called “Tempio di San Biagio“.

Masterpiece by Angelo da Sangallo, it is considered ti be the tallest building with a Greek cross plan of Renaissance architecture enthroned in the middle of a green lawn.

You will find it just off the city center. Absolutely part of the things to see in Montepulciano!

Pulcinella Tower

torre di pulcetta montepulciano

The sotry of this Napolitan symbol in the heart of a Tuscan city remains today a mistery. But this clock is still working and regularly strikes the time on a bell from the top of one of the tower of Sant’Agostino church.

Stories about its origin are many. A fascinating and mysterious object.

Sant’Angostino Church

Tre statue sopra ingresso principale, madonna nel mezzo

Walk up the streets of Montepulciano, a pleasant stroll among quality shops and restaurants and suddently, there, in front of you, you will find a beautiful white stone facade decorated with modules of the late Gothic Florentine. You will also be amazed at the terracotta relief with “Madonna and Saints Battista and Agostino“.

To be found somewhere inside the medieval city…

Where to eat in Montepulciano

There is so much choice of quality! The good restaurants are numerous, we have even written an article on this only that you can read here.

Val d’Orcia and Val di Chiana are territories famous for the quality of their meat. We advise you to taste the Fiorentina di Manzo Chianino. To name just a few restaurants:

  • Osteria del Borgo located on the main square, serves traditional Tuscan dishes
  • La Grotta located a little outside the center, a quality restaurant
  • Le Logge del Vignola, recommended by the Michelin Guide. More modern but very good dishes

La Vecchia Posta restaurant

located in Bagno Vignoni about 30 minutes by car from Montepulciano, it serves dishes of the pure Tuscan tradition. Elaborated with fresh and local ingredients and accompanied by the wines of the territory, candlelight dinners and under the starry sky and often accompanied with soft live music.

Find out more

Events in Montepulciano

In Montepulciano you will find an almost endless list of events throughout the year! The municipality’s official website offers an interactive calendar that is very pleasant to use. See here.

The Easter Festival is undoubtedly an event not to be missed! A unique opportunity to experience an exciting total immersion in Beauty. The architectures and paintings of Nature and Humans intertwined and accompanied by live music.

What to do in Montepulciano if it rains

best wine tour in tuscany

As you have seen in this article, there are numerous things to do in Montepulciano, outdoors but also indoors.

We didn’t have much time to talk about wineries where you can taste wine, an activity that lends itself very well to rainy days.
A very brief introduction anyway:
in Montepulciano wines are produced with mainly Sangiovese grapes. Full-bodied red wines that age well, to be enjoyed with red meat. If you are interested you can read more here. In a very short time, here are some wineries where you can taste Montepulciano wines:

For those traveling with the family, or like us who love chocolate, we recommend a stop at the Montepulciano Chocolate Laboratory.

We hope you enjoyed this article and that you will have a wonderful time in Montepulciano.