Montepulciano Travel Guide: 4 days to explore this beautiful Tuscan hill town!

montepulciano village at sunset

The past December we’ve spent 4 fantastic days in Montepulciano, a perfect base to discover and explore the Val d’Orcia, the Crete Senesi, and the Valdichiana, actually amongst the most beautiful and suggestive areas of all Tuscany.

The most amazing and fascinating photos you see of Tuscany come right from this heaven, especially from the Natural and Cultural Park of the Val d’Orcia region, that has indeed been declared a Human Patrimony by Unesco. That’s a real paradise!

The Val’Orcia is a large valley stretching to the south of Siena, it is crossed by the river Orcia, from which it takes its name, and is characterized by magic and undulating landscapes, soft hills and cypress trees, ancient medieval towns on top of the hills, castles, charming farmhouses, thermal springs, and much more.

Well, for this short vacation I really wanted to try the experience of staying right in the historical center of a fairytale medieval village, and I decided for the magnificent town of Montepulciano, so perfectly preserved and so intriguing that is considered amongst the most beautiful borghi or hill top village of Italy!

Perched on top a hill, Montepulciano is located right on the border between the Val d’Orcia and the Valdichiana, and is surrounded by countless vineyards, green hills, and forests. The name of the town is in fact associated to the great and famous wine produced on its hills: the Vino Nobile of Montepulciano, one of the most famous and appreciated Italian red wines.

Montepulciano is known as the perla del’500, a real jewel of art and beauty, a typical Renaissance town where all is incredibly beautiful and perfect.
That’s the birthplace of Agnolo Poliziano, great humanist considered as one of the major poets of the 15th century; he worked under the protection of the great Lorenzo il Magnifico and was also tutor to the Medici family in Florence.

This charming Tuscan town actually houses some of the most remarkable masterpieces of the Florentine Renaissance, such as the tombstone of Poliziano, carved by Michelozzo; the wonderful ceramics of Della Robbia at the Museo Civico, the Holy Family with the young Saint John by Sodoma, and the Madonna and Child by Luca Signorelli, in the church of Santa Lucia.

The village develops around Via del Corso, the main town’s street, where elegant and sumptuous palaces, ancient churches and historical buildings succeed one after the other; a series of narrow alleys depart from Via del Corso, offering amazing views over the surrounding countryside.

I booked my stay at the characteristic Osteria del Borgo, a typical osteria and wine bar serving local specialties, such as salami, local cheese and a fantastic wine. I had dined there 2 years before.
I remembered the panorama from the osteria’s terrace was enchanting, and then I came to know they had recently restored the rooms and apartments of their palace.

The accommodation was a real surprise! Very good value for money!
I had booked an apartment for 2 with hydromassage bath, but when we arrived to the wine bar for the check in, the very kind staff upgraded our accommodation to a larger apartment with view over the valley.
That was a beautiful rustic apartment with kitchen, living room with comfortable sofasand 2 large windows with an incredible and amazing panorama over the Temple of San Biagio and the hills of Siena and the Val d’Orcia! Simply wonderful 🙂

The apartment is furnished in typical Tuscan style, with warm terracotta floors and beamed ceilings; on the upper floor, the very romantic bedroom was waiting for us with a large bathroom with hydromassage bathtube.
The windows right on the roof created a very suggestive atmosphere, especially at night, when, lying on the bed in the dark, we could admire the stars and the beautiful bell tower of the Palazzo Comunale, rising right above our heads.

We were right next the main square of Montepulciano, the scenic and wonderful Piazza Grande, surrounded by majestic palaces like the Palazzo del Capitano del Popolo, Palazzo Contucci, home to the Consortium of the Vino Nobile of Montepulciano and hosting ancient cellars where you can taste wine, the magnificent town’s hall with its bell tower, work of Michelozzo, and the Duomo with its unfinished facade.
On one side of the piazza stands a wonderful well or Pozzo dei Grifi e dei Leoni, whose eroded ancient stone can only let you imagine how old this place is.

Being in Montepulciano arund the 8th of December we were glad to find an interesting Christmas market, in the lovely setting of the Logge delle Mercanzia in Piazza Grande; I bought a lot of nice and original gifts:-)


One evening we had a fantastic dinner at the restaurant Aquacheta, serving a fantastic bistecca fiorentina! The food is excellent but the restaurant is a bit too touristic and always overcrowded.
Right after the dinner at Acquacheta we went out for a walk among the tiny streets and corners of Montepulciano together with our sweet dog.
The whole village was all for us! Very few people could be seen around, and we really enjoyed the suggestive and silent atmosphere.

We then entered a narrow and dark alley, indeed called Borgo Buio and our attention was captured by the lights and elegant entrance of another restaurant: da Elda e Pier.
It was almost midnight, and while we were reading the menu, the owner of the restaurant came out to talk with us; we had already had our dinner, but he invited us to enter and offered us a drink; a delicious home-made Vin Santo!

The interior of the restaurant is incredibly appealing, made even more fascinating by the choice of the furniture and the many original and lovely objects.
The restaurant occupies the ancient cellars of Palazzo Venturi, and is charaterized by splendid vaulted ceilings, a magnificent well in travertine stone covered with coins, and an underground cave, that was used as a barn in the past.

Pier is an amiable and very hospitable person, we had a long and convivial conversation with him about food culture and many other topics.
Next time we will surely try this restaurant! Can’t wait to come here again!

Montepulciano has a unique silhouette and serves as a very strategic location to visit some of the most beautiful sights of Tuscany: Montalcino, San Quirico d’Orcia, and Pienza on the east side, Cortona and the wonderful Trasimeno Lake on the west side, without forgetting the magic region on the north: the lunar and almost unreal landscapes of the Crete Senesi, immediately south of Siena.

Actually Montepulciano is a great home base to explore the southern part of Tuscany, you can read more on this itinerary of two weeks in Tuscany, where I also speak about the best day trips from Montepulciano.

While here are my itineraries from Montepulciano 🙂

Montepulciano Location on the Map

Visualizzazione ingrandita della mappa


  • Michael ha detto:

    Hi Elena – Your site is awesome! My wife and I are planning at trip to Tuscany and this has been our #1 source….so thank you. We are hoping to stay in Montepulciano for 2-3 nights, and unfortuantely Osteria del Borgo does not have availability. Might you have any other suggestions? Thanks again!

    M & T

    • elena nacci ha detto:

      Hi Michael,
      I’m so happy to hear that my site was helpful in planning your trip 🙂

      Other great properties to stay are Palazzo Nobile di San Donato, a wonderful historical residence facing the beautiful Piazza Grande, next the Town’s Hall, and the charming Locanda di San Francesco, refined B&B with splendid views.

      Feel free to ask any other question,
      Have a great Tuscan stay!

  • Anjaan ha detto:

    Hi Elena,
    My concern is the mode of travel in Italy.

    I plan to visit Montepulciano on my way back from Venice. I would like to stop at Florance. What are the travel options available to me as I will not drive ? I would prefer to travel by bus or train.

    Neel Nag

    • elena nacci ha detto:

      Hi Neel,
      thanks for your message.
      You can take a train from Florence, change train to Chiusi-Chianciano Terme station and then another train to reach Montepulciano. You’ll take about 3 hours to get to Montepulciano.
      You can check train timetables on
      I remain at your disposal,

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