Montepulciano With Kids – 8 Best Things To Do + Helpful Tips

At first glance, Montepulciano doesn’t seem like a great place to bring your children. The hilltop Tuscan town is best known for its wines and Renaissance architecture – not exactly big draws for the little ones!

But, there are actually quite a few things to do in Montepulciano for kids and a visit to the Tuscan town can be fun for the entire family.

Montepulciano Basics

How To Pronounce Montepulciano

Montepulciano (mohn-tay-pool-CHAH-noh) is located in Southern Tuscany, between two valleys – Val di Chiana and the UNESCO World Heritage site Val d’Orcia.

Listen to it here:

When To Visit Montepulciano With Kids

It’s best visited with kids in the spring through the fall. Winter in Montepulciano is quite cold and some of the attractions for kids are closed. There are plenty of other great things to do in the winter in Tuscany.

How Long To Spend In Montepulciano With Kids

Boys walking through the archway of the Porta al Prato in Montepulciano Italy.

I recommend combining a visit to Montepulciano with a visit to neighboring Pienza. You can see both (with kids!) in a day.

Our family usually makes a day trip from Florence. We visit Montepulciano in the morning and Pienza in the afternoon, having dinner in one of the two towns or an agriturismo in the Val d’Orcia.

Where To Stay When Visiting Montepulciano With Kids

I recommend staying outside of the Montepulciano city walls. Agriturismi (countryside farm accommodation) in the Val d’Orcia are the best places to make a home base in the area if you have little ones. Look for one with a pool and outdoor areas to play. Some also have farm animals, cooking classes, and other kid-focused activities. A couple of great options include:

Agriturismo La Fonte – La Fonte’s apartments make a perfect home base for couples or families.  The (non-fenced) pool, stunning views, and on-site brewery will make it hard to leave to explore the area!  There’s a little play area for kids and the food at the restaurant is worth a visit, even if you don’t stay here. 

Agriturismo Il Rigo – On a dirt road between Pienza and San Quirico d’Orcia.  I love this agriturismo as a base for walking because you’ve got access to all the strade bianche (dirt/gravel) roads in the valley.  It’s quiet, peaceful, and the food and owners make it memorable.

The 8 Best Things To Do With Kids In Montepulciano

Explore Underground Passageways

Entrance to Cantina Ercolani.  The sign is below the stone archway entrance and there is a wooden sign with yellow painted 'città sotterranea.'  There is a knight in armor on the right and there are boxes of wine bottles around the door.  You can see inside is full of wine displays.

Just after entering town through Porta al Prato, you’ll see the Cantina Ercolani and a sign for ‘Città Sotterranea’ or Underground City. You can walk down into the historic underground passageways and see armor, the cisterns, a wishing well, the wines aging in barrels, and more.

You can easily spend 30-40 minutes wandering around if your kids are interested in looking at everything.

Our kids love looking at the armor, making a wish, and looking up through the ceiling grate to see people walking by on the street.

It’s free and the shop owners are friendly and don’t pressure you to buy anything (although the wines are great and they’ll let you sample with nibbles!).

Find Pulcinella

Kids and adults will have fun finding Pulcinella and watching him ring the bell.

Can’t find him? Hint – look up! He’s on top of the bell tower of the Sant’Agostino church, just up the hill from Porta al Prato.

Try to time it so you can see him ring the bell on the hour. If you get there early, walk into the church, head to the back left, and see the permanent presepe (nativity scene). Or, grab a quick snack in the Baccano bar at the base of the tower.

Time for a potty break? The town’s public WC is to the right of the Sant’Agostino church.

Play in the Playgrounds

Boy on motorcycle toy in playground in Montepulciano Italy.  The fortezza is in the background, along with a bush labyrinth, a swingset, and benches.
Playground at the Fortezza

Montepulciano has two playgrounds for kids. One is just outside the city walls near Porta al Prato. The other is in front of the Fortezza (fortress) at the other end of town. Our kids enjoy both of them. They especially love running around in the labyrinth-like bushes in the Fortezza and looking at the huge sculptures.

If you go to the Fortezza playground, take a few minutes to walk inside the building and show your kids the transparent floors in the Enoliteca. You can see the ruins under the floors!

If you go to the Porta al Prato playground (Giardino di Poggiofanti), you can walk across the street to the CONAD supermarket to get picnic supplies to enjoy in the park. There are a few benches or you could bring a blanket and sit on the ground.

Be sure to check out our guide to Italian Grocery Stores + 5 Important Things to Know!

Good To Know: If you’re combining your visit to Montepulciano with a visit to Pienza, know that Pienza also has a great little playground (my kids prefer it to Montepulciano’s playgrounds).

Get Gelato

Close up of gelato in containers in a shop.  You can see amarena, fiordilatte alle spezie, noce, fiordilatte, and crema.  There are also the serving paddles in a few containers and the paddles have green handles.

Everyone feels better with a gelato in hand! We don’t have a preferred gelateria in Montepulciano, but we always seek out artigianale (made in-house) gelato.

Good To Know: If you’re wondering if a gelateria is the ‘real deal,’ take a look at its banana or pistacchio gelati. The banana should be greyish if real bananas are used – don’t buy bright yellow (artificially-enhanced) banana gelato. Likewise, pistacchio should be a dull, grey-ish green, not bright green.

Climb Up The Clock Tower

Boy walking toward the clock tower of the Palazzo Communale in Montepulciano Italy.  There are only two people in the piazza ahead.
Sizing up the climb

Montepulciano’s clock tower is part of the Palazzo Comunale (town hall) in the main square, Piazza Grande.

Climbing up to the top is not difficult, and kids (and adults) will feel rewarded with the sweeping views of Montepulciano and the surrounding countryside.

Visit The Twilight Set

An empty Piazza Grande in Montepulciano, Italy.  You can see the Duomo ahead and the Town Hall on the right.

Older kids and teens will love seeing where Bella frantically ran through the crowd to save Edward in the film, Twilight: New Moon (in Piazza Grande). You can also see other places in town and nearby where scenes were filmed.

Choose a Contrada (Neighborhood) To Find in Town 

You’ll see the colorful flags waving from buildings throughout town. The flags mark the territories of the 8 contrade, or neighborhoods of Montepulciano.

One of the largest events of the year in Montepulciano is the Braviò delle Botti, which takes place in August. Teams of two from each contrada race empty wine barrels (weighing around 80kg!) uphill through the town streets, finishing in Piazza Grande. It’s an intense and emotional event for the contrade of Montepulciano and definitely worth a watch if you’re in the area!

Try to find your favorite flag out of the 8 neighborhoods:

  • Gracciano – green/black
  • Cagnano – green/blue
  • Collazi – yellow/green
  • Le Coste – yellow/blue
  • Poggiolo – white/blue
  • Talosa – yellow/red
  • Voltaia – red/black
  • San Donato – white/red
Red and white flag hung from a wall in on a tiny street in the San Donato neighborhood in Montepulciano Italy. The buildings are red brick and stone and there is also an old iron lamp and a stone crest of the Medici family.
Flag of the San Donato contrada

Go On A Scavenger Hunt

Print this Montepulciano Scavenger Hunt for your kids:

Montepulciano Events For Kids

Montepulciano’s annual events calendar is packed. The town events that will appeal most to kids are:

Bravìo delle Botti (August)

This is the event to see in Montepulciano.  It’s like Siena’s Palio, but instead of racing horses, the neighborhoods race wine barrels! 

Teams of two from each contrada (neighborhood) roll 80kg(!) empty wine barrels over one kilometer uphill through town to Piazza Grande.  The winner receives the ‘Panno,’ a painting on a piece of fabric. 

Competition is fierce and emotions run high.  It’s a fun and exciting experience for kids and adults.

Natale a Montepulciano (December)

Montepulciano hosts one of Tuscany’s largest and most adored Christmas markets. It’s our family’s favorite Christmas market in the area. The bulk of it is in Piazza Grande, and Santa’s Village is up the street in the fortezza (fortress). You’ll find local food products like cheese and wine, along with Christmas ornaments, wooden presepe (nativity scenes) and other gift ideas.

The market begins at the end of November and finishes at the beginning of January (usually after the Epiphany on January 6th).

Nearby Places To Visit With Kids

PlaceDistanceTime (by car)Highlights
Pienza15 km20 minEat pecorino cheese, take a walk along the city walls or in the valley below, play in the playground
Chiusi25 km25 minWalk or ride bikes on the Sentiero della Bonifica, a 60 km path between Chiusi and Arezzo
Bagno Vignoni25 km30 minSoak in the ancient Roman thermal springs
Cortona30 km40 minLearn about the Etruscans at the MAEC museum
Siena60 km1 hourRun around in the Piazza del Campo, learn about the Palio
Monteriggioni80 km1 hour 10 minWalk on top of the medieval walls, visit the Armor Museum
Florence110 km1 hour 20 minSee Michelangelo’s David (and read about him first!), climb the bell tower
Rome180 km2 hoursExplore the Roman forum, visit the Colosseum, go to the Children’s Museum

If you’re looking for more fun things to do with your kids in Tuscany, check out:
70 Things To Do In Tuscany With Kids (That Parents Will Enjoy Too)
Visiting Brolio Castle (Castello di Brolio) With Kids
Visting Pinocchio Park
Forte dei Marmi With Kids – 11 Best Things To Do
Exploring the Zoo di Pistoia (Pistoia Zoo)

I hope you enjoy your visit to Montepulciano with your kids – divertitevi (have a great time)!