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Two shelves of oak barrels aging vin santo in Italy.

Things To Do In Montepulciano – These are the Best Activities For Your First Visit

Last updated on February 22nd, 2024

Although Montepulciano is a small town, it has so much to offer, no matter the size of your group, your agenda, or your time restrictions.

I have been coming to Montepulciano for over 10 years now (including five days a week for the last four years). After countless mornings wandering the streets of Montepulciano, with and without my children, I have come down to a pretty solid list of the absolute best things to do in Montepulciano.

In this comprehensive, in-depth guide to things to do in Montepulciano, I will take you through my top choices in terms of what to do, see and eat while in this beautiful Tuscan village, including practical information such as:

  • Ticket information
  • Pre-booking requirements
  • Best times for each activity
  • Personal tips based on experience
  • My favorite spots for wine and food in Montepulciano

All of the suggested activities below are based on my first hand experience over the years, giving me insider-information about how to make the very best of your time in Montepulciano.

Fore more practical information about parking, driving, travel within Montepulciano, shopping and public restrooms in Montepulciano, read A Local’s Guide to Montepulciano, Italy.

Visit an Underground Wine Cellar

Large wooden wine barrels stacked in a stone corridor at the Talosa winery in Italy.

Best Time To Visit: Right after lunch when it’s hottest during the day.

In the historic downtown of Montepulciano, you will come across the eight historic wineries or cantine, as we call them in Italy. They all offer a variety of tours, tastings and group events, including visits to their one of a kind underground cellars. 

Each of the eight historic wineries has their own percorso or way to visit the underground wineries. We had the most fun at the Cantina Talosa because of how deep it was underground. I also like this winery because you can visit underground without pre-booking a tour.

In other wineries such as the Cantina De’ Ricci or at Fanetti – Tenuta S.Agnese, you are required to pre-book your visit. At Città Sotterranea di Ercolani, you must book but it’s a free tour (best for smaller children). I suggest you stop by in the morning and ask when they have a tour in English and sign up right away. They tend to fill up quickly in the summer.

Large wooden barrel next to stacked smaller barrels in an underground winery in Montepulciano, Italy.

Good To Know: If you want to visit these wineries and have a more complete experience, you can pre-book exclusive tours, independent tastings with local products or group events.

Another Cantina that sticks out to us is Contucci, the oldest of them all, dating back to 1008. Simona, the director of sales, recently explained to me that the winery is currently under the 41st generation of management within the Cantucci family – pretty impressive!

Tip: This is a great activity to do in the middle of the day to beat the Tuscan heat. The underground cantine is cool and refreshing!

Visit Piazza Grande

Piazza Grande, empty, in Montepulciano, Italy.

Best Time To Visit: Anytime but best at aperitivo hour starting at around 6:00 pm.

Piazza Grande is the largest and main square in Montepulciano although it’s quite the hike to get to! Here you will find a bar to sit down and rest your tired legs, some of the oldest historic wineries, the town hall, the Cathedral of the Assumption , Palazzo dei Capitani del Popolo, and the Well of the Grifi and the Lions.

As of early 2024, the Cathedral of Saint Mary is closed because of an enormous restoration underway. Their tourist office told me it won’t be for a couple of years before it will be open to the public again.

If you want to enjoy the square and have your kids run freely, consider sitting down at the bar for coffee. If, however, you are looking to sample wines, stop in at the Enoteca Contucci where you can either order wine by the glass, bottles and/or cheese plates and charcuterie boards.

Get Festive: If you’re in Montepulciano during the holidays, don’t miss the Christmas market in Piazza Grande!

The main fountain with lion statues on top and sand-colored stone buildings in Piazza Grande in Montepulciano, Italy.

This is also where you will find the tourist office, located just next to the fountain. This is one of my family’s favorite squares in all of Southern Tuscany because of its size. The best time to come and hang out is for aperitivo when children will be playing and the square will fill up with locals.

Good To Know: Montepulciano isn’t an amazing town if you need to use a stroller or wheelchair. To get to Piazza Grande, you must climb some steep cobblestone streets. If you have trouble making your way up, consider taking the Gran Tour on the trolley (read more below), which will take you right to the top.

Climb the Clock Tower on Palazzo Comunale

Empty Piazza Grande in Montepulciano. You can see the bell tower and church on left and town hall and clock tower on right.

Best Time To Visit: Morning at 10:00 am at opening before it’s too hot or before closing at 6:00 pm.

While in Piazza Grande, take the opportunity to climb the clock tower for sweeping views of the Valdichiana and Val d’Orcia. This is by far the most athletic activity you can do but it’s not too challenging. I wouldn’t bring my three year old but my five year old did it with no hesitation. 

Montepulciano With Kids: Don’t miss my recommendations for Things to Do with Kids in Montepulciano if you are looking for kid-friendly activities in Montepulciano!

It’s only about 150 steps (compared to the 400+ of Giotto’s Bell Tower in Florence).

Visit the official website for ticket pricing and hours as they change depending on the season. 

Wine Tasting In Montepulciano

Hand holding up wine glass with a small amount of red wine. There are wine bottles stacked and displayed behind it.

Best Time To Visit: Right before lunch or as a pre-dinner activity

Vino Nobile di Montepulciano is the most famous wine from Montepulciano produced throughout the surrounding countryside, characterized by a minimum of at least 70% uva gentile, or Sangiovese grapes. The most basic vintage is aged for two years and then for another in oak barrels (which you can see if you tour the underground cantine).  

I have gone wine tasting at both the historic wineries in Montepulciano as well as at the various enoteche scattered throughout the city. If you are hoping to bring wine home as a souvenir or gift but don’t know where to start, I suggest heading to a enoteca or wine shop where the owner can lead you in the right direction based on your interests.

Display of olive oil bottles and wine bottles - 10 in total - along with brochures and prices. They are on a wooden table in Italy.

If you know you want wine from a specific cantina, go directly to their storefront and ask for a free tasting. If you would like a more extensive and exclusive tasting with cheese, bread and cured meats, these need to be booked in advance.

My favorite enotecas in Montepulciano: Need help picking which wine shop is right for you? Read Top 5 Enoteche in Montepulciano.

Narrow stone street between buildings leads to a cantina in Italian town of Montepulciano.

My favorite vecchie cantine (historic cantinas) in Montepulciano:

  • Cantina De’ Ricci
  • Contucci
  • Fattoria della Talosa

To learn more about the historic wineries in Montepulciano, read about Visiting Montepulciano’s Cantine Storiche.

Or, if you want to visit a vineyard in the Montepulciano countryside, check out Avignonesi.

Visit Fortezza Medicea

Kids playground shaded by tall trees in Montepulciano. You can see the fortezza in the back right.

Best Time To Visit: Anytime but especially nice to get out of the sun in the late morning or after lunch.

This Medici Fortress sits just off of the main square of Montepulciano and although there isn’t much to do there, unless you are interested in wine tasting, it’s a great place to sit down in the shade and enjoy a breath of fresh air. The fortress has a small botanical garden with mazes, a couple of play structures and large animal sculptures.

Sometimes I bring my boys up here to run around. I know that after we hike up to the Fortezza from the base of Montepulciano and then run around, they are bound to be tuckered out!

Main entrance to Enoliteca in Montepulciano, Italy. Brick archway in front of door. Chalkboard sign to left of door.

Inside the fortress is the Enolieca Consortia Vino Nobile, an enoteca with a very modern self-service formula serving up wines solely from Montepulciano. The staff will assign you a card which you can then scan at various stations and fill your glasses up with over 70 bottles of wine open at any given time. Choose a table and keep helping yourself to either tastes or full glasses.

We prefer to sit on the outdoor terrace but the indoor space is also quite interesting as it rests atop an archeological site.

The Civic Museum

Tile sign for Museo Civico on a stone wall in Montepulciano.

Best Time To Visit: Right after lunch when it’s hottest during the day. 

The Civic Museum is Montepulciano’s main museum full of various Etruscan artifacts and famous pieces of art. If you are only spending one day in Montepulciano, I don’t recommend spending time here because there is so much else to do and see! Visit the official website for ticket information and hours as they change seasonally.

Good To Know: Montepulciano also has a Torture Museum but I find it kind of gruesome, which is why it’s not on my top list of things to do in Montepulciano. It’s located between the Fortezza and Piazza Grande.

Sample Pecorino Cheese

Display of whole pieces and chunks of pecorino cheese in a display case along with a handwritten price list.

Best Time To Visit: Anytime of the day

If you come to Southern Tuscany, one of the best things to do in Montepulciano is eat the local pecorino cheese. You can do this at either one of the wineries, restaurants or wine shops, where you can order a glass of wine and a tangliere di formaggio, a cheese board.

Tip: Brining pecorino cheese home is easy. Just ask for it sottovuoto, meaning vacuum packed and you should be all set. Note that you cannot bring fresh pecorino cheese into many countries such as ricotta.

Entrance to cheese shop in Montepulciano. You can see the cheeses in refrigerated cases inside.

If you are a true cheese lover, don’t miss Cugusi cheese shop, located towards the base of Montepulciano. This is one of the most well-known and reliable cheese shops in the whole area. They will happily let you sample whatever you want and don’t miss all their other canned goods, wine and olive oil to bring home as well.

If you are looking to get out of the city walls of Montepulciano, consider a visit to the Cugusi cheese production house, located just 10 minutes outside of Montepulciano on your way to Pienza. 

Packaged cheeses on display in a refrigerated area in a cheese shop in Tuscany.

Here you can order whatever cheese you want and they will put a picnic basket together for you with cured meats of your choice, cups, wine, bread, a cutting board and cutlery. Bring it to one of their outdoor picnic areas and indulge in one of the best things to do in Montepulciano, which is still relatively undiscovered.

Take A Trolley Tour Of Montepulciano

Hand holding tour brochure for Montepulciano, Italy.

Best Time To Visit: Anytime of the day 10:00 am to 6:30 pm

One of the best things to do in Montepulciano for people who need a break from walking (or have had too much wine!) is to sign up for the local trolley tour. The tour lasts about 30 minutes and takes you through the historic downtown of Montepulciano with an audio guide.

The trolly is covered so no matter the weather, you will have a great time. I find this activity a little corny but my boys love it!

The trolley leaves every 20-40 minutes (depending on the time of year) from 10:00 am to 6:30 pm from the base of Montepulciano just before the door, Porta al Prato. The trolley makes four stops including the starting point of Sant’Agnese, Piazza Grande, Tempio di San Biagio and Pulcinella (upon request).

Woman speaking to driver of a red trolley in the Piazza Grande in Montepulciano, Italy.

Good To Know: The Montepulciano trolley ticket has a “hop-on, hop-off” formula, allowing you to get off at various stops and get back on when you are ready to continue your tour. 

Visit The Churches

The inside of the Chiesa del Gesu in Montepulciano, Italy. You can see the pews, paintings, and the decorated ceiling.

Best Time To Visit: Anytime but Sunday mornings when mass is being held (unless you wish to attend a Catholic service). 

Montepulciano has several churches to visit both inside and outside the city walls. The main church in Piazza Grande, the Cathedral of Saint Mary, is currently (October 2023) being restored and cannot be visited from the inside. 

Facade of a stone church in Montepulciano, Italy.

Instead, check out Sant’Agnese Church just outside Porta al Prato at the base of Montepulciano, or the Chiesa del Gesù, about halfway up to the top of Montepulciano or the Sant’Agostino Church. 

Catch A Panoramic View Overlooking Southern Tuscany

Panoramic view of Tuscan countryside from village of Montepulciano, Italy. You can see terracotta rooftops in the foreground.

Best Time To Visit: At sunset for aperitivo at E Lucevan le Stelle – Wine Bar Bistro

Once you arrive in Piazza Grande, you can go behind the bar to one of the various terraces overlooking Southern Tuscany where you can catch a glimpse of the Temple of San Biagio.

I think the best lookout is actually in Piazza di S.Francesco where I also suggest the restaurant E Lucevan le Stelle – Wine Bar Bistro overlooking the valley. Sit down for either a glass of wine, a charcuterie board or a full meal.

Fact: The Val d’Orcia valley is considered a UNESCO World Heritage site in itself.

Temple of San Biagio (Chiesa di San Biagio)

View of San Biagio chuch. People walk up to it and stand off chatting on the right.

Best Time To Visit: Anytime of the day but I prefer later in the afternoon when the golden hour starts. 

The Temple of San Biagio is one of the absolute best things to do in Montepulciano, hands down. Ever since I moved to the area, this has been a favorite spot for us to come and enjoy an afternoon snack.

To visit the inside, you need to purchase a ticket for €3.50 (children under the age of 6 enter for free).

The church was built between 1518 and 1548 and although relatively new compared to other churches in Italy, this one sticks out in terms of architectural importance. You can walk here from the center of Montepulciano but it’s a bit far. I suggest taking the trolley or driving (you can park right in front of the temple).

Entrance to La Grotta restaurant in Montepulciano, Italy. There are red Michelin plaques to the left of the door.

The restaurant, La Grotta is also very good but I don’t suggest it with small children as it’s a little more expensive than other places and the menu is limited and seasonal.

My Personal Tips For Visiting Montepulciano

Panoramic view of Tuscan countryside and San Biagio Temple from Montepulciano, Italy.
  • Take advantage of full days and start walking around before the crowds start to come out around 10:00 am
  • Note that most shops don’t open until around 10:00 am
  • Be sure to rest if you are visiting Montepulciano in the summer. It can get quite hot. Book indoor tables at lunch and outdoor tables at dinner.
  • Pre-book underground cellar tours in the height of tourist season.
  • Please be mindful of wine tasting at the wineries. Most wineries expect you to buy something if you are participating in a free tasting. They are not meant for tourists to go around sampling every wine possible but rather, an opportunity to get to know the story of each winery and to get to know the individual wines. 

More Tips: For my suggestions of where to eat and drink in Montepulciano, read Montepulciano Restaurants, My Favorite Enoteche in Montepulciano, Montepulciano’s Historic Cantinas and The Best Bars in Montepulciano.

Other Towns To Visit Near Montepulciano

Small square in an Italian village. It's surrounded by stone and brick buildings. No one is in the square.
San Casciano dei Bagni

If you are planning a trip to Montepulciano and wondering how to fill the rest of your time, consider these day trips to fill your day:

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