Montepulciano, Italy: The Incomparable Tuscan Hill Town Perfect For When You Need to Escape The Crowds


I think most of us have special places we’ve visited that will forever be etched in our hearts. Someplace that we compare all others to, yet nothing seems to come close enough. For us (so far), that place is Montepulciano, Italy. We first visited Montepulciano on a whim five years ago in 2012 when we decided we needed to escape Rome because it was overrun with tourists.

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Montepulciano is a medieval hill town in southern Tuscany right near the border with Umbria. The closest major city is Siena. They are world renowned for their superb wine: Vino Nobile di Montepulciano, their cheese: Pecorino Toscano, as well as pici pasta, millefiori honey and other delights.  But the best part of Montepulciano is the panoramic view from pretty much anywhere in town, overlooking the vineyards, farmland, and sprawling villas of the Val d’Orcia and Val di Chiana valleys. 

It has gotten a little more touristy over the years due to being a filming location for one of the Twilight movies, but still much quieter than the big cities even in the summer.

One of the gates into the walled city of Montepulciano

Where to Stay in Montepulciano

Montepulciano saved our Italy vacation in 2012, and just recently on our latest trip to Italy, it saved the day again. As a result of two Airbnb mishaps in a row, we fled to Montepulciano and sought refuge at our favourite hotel, Camere Bellavista. This is a small family-run hotel with only 10 rooms, most of which have a fantastic view of the valley below, and one with a panoramic terrace (room 6). It is a no-frills hotel, but has everything you need, is always clean and comfortable, and the view can’t be beaten.

View from our room in Camere Bellavista.

View from our room in Camere Bellavista.

What To Do and See In Montepulciano

While small, this town is packed with things to do and see, and even though we’ve visited twice, we haven’t done everything. Main sights include:

  • Piazza Grande, which holds the unfinished cathedral and Palazzo Communale (town hall). You can climb up the tower (€5) of Palazzo Communale for even more breathtaking views of the surrounding valleys.
Palazzo Communale

Palazzo Communale

View of the piazza from the tower

View of the piazza from the tower

  • Church of Saint Augustine
  • Civic Museum
  • Torture Museum
  • Church of San Biagio (below the town)
  • Wineries 
    • Contucci - one of the “founding fathers” of Vino Nobile, they have been producing wine since the Renaissance. Tasting is free and there is no pressure to buy, but it is hard not to once you taste it! They also have a small cellar you can take a tour of.
    • Poliziano - A newer addition to the Montepulciano family, but impressive all the same. Also has a cellar you can visit.
    • De Ricci - Boasts the most impressive cellar inside an ancient Etruscan cave.
    • There are many more wineries and I’m sure they are all spectacular, however, these are the three we tried.
Marcin inside the Etruscan cave under Cantina De Ricci

Marcin inside the Etruscan cave under Cantina De Ricci

  • Of course like anywhere else in Tuscany, there are many food and wine tours you can take as well.
  • But the best thing to do in Montepulciano is to roam around and explore the small alleyways and winding streets filled with little shops and restaurants.
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What To Eat in Montepulciano

Ah, the most important question about any town we visit - where to eat? Fortunately this tuscan hill town is chock full of delicious food.  Our top two choices for lunch and dinner are:

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Osteria Acquacheta - a small, rustic restaurant with shared seating and reservations almost always required due to its immense popularity. Everything here is made with fresh, local organic ingredients. There is a standard menu with their usual fare (mostly pici, the local pasta and gigantic steaks) always posted outside, but the real gems are on the daily menu they give to you handwritten on a sheet of paper. It is always in Italian, so sometimes you may need to break out your translator app. 

Don’t shy away because of the shared tables, because you will miss out on something great.  The other great thing about this restaurant? The price. This last visit we got bread, sparkling water, half-bottle of wine, two appetisers, two entrees, a delicious post-entree baked cheese and pear dish, and dessert for only €34 total. Bonus? In lieu of a traditional cheque at the end, the quirky owner/chef comes out and tallies your order on the paper placemat.

Ristorante ai Quattro Venti - don’t be put off by this restaurant being located right on Piazza Grande. It holds its own with delicious homemade food and is not touristy like you might think. This was the first restaurant we ever visited in Montepulciano, where we took refuge from the rain on the first day of our 2012 visit and were introduced to the wonders of Pecorino Toscano and millefiori honey. We visited once more on that trip and would have visited again on this most recent trip if it wasn’t closed for the holiday season.

Caffe Poliziano - this is the best option for breakfast or anytime you want any sort of coffee/tea and pastry. Open from 7:00am to midnight, it is easily the most versatile eatery in town, with options for panini in the afternoon, and some dinner selections in the evening as well.

When To Visit?

The first time we visited it was the tail-end of summer, so everything was open and the weather was good except for the first day when it rained on us. Bonus: if you visit at the end of August - “Bravio della Botti”, an uphill wine barrel race occurs on the last Sunday of August every year. Contestants push huge wooden wine barrels for about a kilometre uphill, ending at Piazza Grande. The winners receive the “bravio” (a painted cloth banner depicting the town’s patron saint) at the end of the race.  Preceding the race the town participates in a “costume parade” where all of the original families of the town parade around in their spectacular medieval costumes waving their family flags. This tradition has been going on since the 14th century and if you are in the area at the time is a must see! You can see the various family flags hanging in different parts of town throughout the year.

The second time we visited was in December, so of course the town was decked out in Christmas decorations, and had its Christmas market on the weekends. While much colder than in the summer, it was still sunny during the day, and if you like Christmas festivities, this would also be a great time to visit.  Except for when the market was open, Montepulciano was much quieter this time of year as well, so it was very peaceful and easy to walk around.

Personally, we love this town so much we would visit any time of year.

Church of San Biagio

Church of San Biagio

Cat in the window along one of the streets in Montepulciano

Cat in the window along one of the streets in Montepulciano

How To Get There

There is free parking available outside of the walls, so you can drive, however, can be very difficult to find a parking spot even in the off-season, so we would recommend coming by train if you can. 

Don’t be fooled by the Montepulciano Stazione stop, as it is a tiny station and buses rarely pick up from there. We made that mistake the first time we visited, but luckily ended up sharing a cab with two girls from New Hampshire who also made the same mistake! 

An easier way to get to the town is to take the train to the Chiusi train station and catch the bus to Montepulciano from there.  It will drop you off at the bottom of the hill outside the wall and then you can make your way up (stopping to check out all the cute little shops!) to Piazza Grande at the top.

One of the many gates into the town

One of the many gates into the town

Piazza Grande at night with Christmas market set up

Piazza Grande at night with Christmas market set up

Another look at the breathtaking view

Another look at the breathtaking view

No matter when you go or how you get there, trust us, this town is worth it to enjoy the streets, the views, the food and the wine.

Do you have a place you visited to which you compare all others? What is your favourite place you have visited? Let us know in the comments!

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