#lavitasieme - A DAY IN MONTEPULCIANO

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For the next few weeks, our La Vita Sieme series will be exploring Montepulciano! This is one of our absolute favorite towns in Tuscany, nestled into the southern Val D’Orcia region. You may recognize that name as we have visited this reason before. There is a reason we keep coming back here. With picturesque rolling hills, ancient hilltop towns and some of the best wines in the world (here’s looking at you Brunellos and Vino Nobile), it is no surprise that almost every “Tuscan/ Italian Roman movie has been filmed here, from Under the Tuscan Sun to Gladiator.

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Sieme Pro tip 1: There is Montepulciano and Montalcino. It is easy to confuse the names, but they are about a one-hour drive apart. And when it comes to wine, they could not be more different. Don’t worry… we will get into that next week!


Montepulciano is a medium sized hilltop town famous for producing Vino Nobile di Montepulciano. Walking through the cobblestone streets today, you can experience the town as it stood more that 500 years ago. However, many structures underneath are even older, believed to date back to the 6th century A.D.! Next week we will explore all about the history of Vino Nobile di Montepulciano and highlight our favorite 700-year-old family-owned winery. Today, we are giving you our Sieme recommended way to spend a day in Montepulciano.  

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 Because Montepulciano is nestled between 2 gorgeous valleys, it was often fought over by the nobility of historically famous rival cities, Florence and Siena. Therefore, Montepulciano was heavily invested in as each city fought for control over its jurisdiction and trade routes, often trying to outdo each other. Today we can thank both Florence and Siena for their animosity. It has gifted us so many incredible towns, churches, museums and palazzos throughout Tuscany, all in the name of ego!

To reach the town you will want to rent a car or hire a driver. (and when you do come to Tuscany again, we can recommend some tour guides!) On the way up the hillside, make sure to stop and marvel at the Church of San Biagio built in the early 1500’s. It is widely considered a masterpiece of Southern Tuscany.

The Church of San Biagio constructed from 1518 - 1540

The Church of San Biagio constructed from 1518 - 1540

The view driving up to the church

The view driving up to the church


Sieme Pro Tip 2: All of these hilltop towns usually have parking just outside the city center as only those with special licenses who live inside the old city walls can enter. These roads were certainly not built with cars in mind! So, consider this your friendly reminder that you will usually need to walk up hill a bit on cobblestone streets.  We can’t stress this enough, wear comfortable shoes!


Make sure to call ahead and make a lunch reservation unless paninis and mixed meat and cheese plates are enough for you! Montepulciano has some amazing restaurants. My favorite is Rosso Rubino, a husband-and-wife team whose typical southern Italian dishes are some of the best I have ever had. You know it is good when they don’t even offer a fixed menu. The daily dishes are written on a blackboard based on the best seasonal ingredients. Make sure to order the fresh pici (pichi) pasta. This is a local delicacy of Montepulciano. Similar to spaghetti but hand rolled and much thicker, it is my favorite pasta! I would also recommend the roasted duck (d’anatra) and the vegetable soup. Pair with a Rosso di Montepulciano, the local typical table wine for a true Tuscan lunch! As this place is small and fills up fast with locals, make sure to call ahead and make a reservation, or ask your driver to do so if you don’t feel comfortable trying to muddle your way through the language barrier.

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After lunch, walk up to the lookout point at Piazza San Francesco. This is one of the most breathtaking views in all of Montepulciano. Stay a while and just marvel at its existence. Being here always makes me feel so much gratitude.

The view from the look out point over Val D’Orcia

Montepulciano is filled with famous artisanal shops. From mosaics, to paintings, to wood carvings and more, pop in and out of these little shops for the afternoon. On the corner of the lookout vista is a famous art gallery called San Francesco Art. Take a stroll inside. You just might find something that you’ll want to hang on your wall at home to remember this amazing little town!

Click the photo to discover more about the gallery!

Click the photo to discover more about the gallery!

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Take the afternoon to wind your way in and out of shops until you reach the Piazza Grande. The grand square is flanked by the Palazzo Communale (the town hall), Palazzo Contucci, (the largest palazzo in the town) and the Church. Meander through each building to be transported back to the 16th century. The Contucci family still lives in this palazzo where they make wine and give tours!  The town square is lined with cafes and hosts summer concerts and fairs in the warm weather months. We recommend sitting along the piazza for an espresso and dolcetto (something sweet) in the afternoon and soaking in the sun!

If art is your passion, pop into the modest Museo Civico for a quick tour of local artists and the Carravagio paintings!

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Around 6:00 p.m. is the perfect time to stop at one of the local bars for an Aperitivo. We recommend heading back to the vista point at Piazza San Francesco where the bar Le Lucevan Le Stella has a great patio overlooking this gorgeous view. Order an aperitivo (we recommend a negroni or spritz) and a “tagliere” (meat and cheese plate) and take in this view at Sunset!

The patio at Le Lucevan Le Stella overlooking the view of the D’orcia Valley.

The patio at Le Lucevan Le Stella overlooking the view of the D’orcia Valley.

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Our Suggested Itinerary 

1.     9:00 a.m. - 10:00 a.m. Get on the road depending where you are coming from.

2.     11:00 a.m. - Stop to see the Church of San Biagio for about 30 minutes to 1 hour

3.     12:00 pm. – 1:00 p.m. Park below the old city walls and stroll the streets for a bit getting the lay of the land.

4.     1:00 p.m. -2:30 p.m.  Lunch at Rosso Rubino

5.     2:30 p.m. -3:00 p.m. Stroll to the look out view point

6.     3:00 p.m. -6:00 p.m. Afternoon Stroll through the city, the Piazza and the Palazzos with a quick detour at the Museo Civico

7.     6:00 p.m. – 7:00 p.m. Aperitivo at Le Lecevan le Stelle

8.     7:00 p.m. -8:30 p.m. Rest for Dinner, or take a passeggiata through the town during sunset (Italian for long walk)

9.     8:30 p.m. -10:30 p.m. Time for dinner!  We really suggest Rosso Rubino if you couldn’t make it for lunch! 

Maybe you would like to stay for dinner in Montepulciano or head back to one of the larger cities like Siena or Florence where you may be based. Either way, don’t plan for dinner before at least 7:30 p.m. Restaurants open for evening seating 7:00 p.m. in Italy. If you would like to stay the night in Montepulciano, don’t worry about running out of things to do. We haven’t even gotten to the best part yet… the wine tastings! Stay tuned next week for where and how to taste the best wines in Montepulciano!

And if you want access to an exclusive wine club with some of the best Vino Nobile you can’t even buy in the U.S.…  make sure to sign up for our newsletter!  


 Thanks for joining us  this week on La Vita Sieme! And make sure to connect with us on social media for more artisanal + sustainable life in Tuscany!

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