Planning your list of things to do in Montepulciano? This hilltop town in southern Tuscany is one of the most atmospheric places in the region, known for its Renaissance architecture, sweeping views over the Val d’Orcia, and its famous Vino Nobile wine.
Perched on a hilltop in Val d’Orcia, Montepulciano is compact but packed with experiences. Beyond wine tasting in historic underground cellars, you can stroll medieval streets, climb the clock tower for panoramic views, and visit the Temple of San Biagio just outside town—one of the most beautiful churches in Tuscany.
We’ve visited Montepulciano twice, in very different seasons.
Our first visit was in July, with our kids (then 9 and 11), at the tail end of a long day through Montalcino and Pienza. We arrived in the late afternoon, walked Il Corso, and had an early dinner, just as a thunderstorm rolled in. The kind that empties a piazza in minutes. Most visitors scattered, but our kids thought it was the best thing that had happened all day. We ended up wandering the rain-soaked streets while water poured off the buildings and rushed down the hill. We didn’t get much sightseeing done that visit, but we got something better: one of those unplanned travel moments you don’t forget.
Our second visit was in October, just Tim and me. Quieter crowds, cooler temperatures, and enough time to properly explore the wine cellars, climb the clock tower, and do the town justice. Between the two trips, we’ve covered Montepulciano thoroughly, and in this guide, we’ll share everything worth knowing.
In this guide, we cover the best things to do in Montepulciano, where to go wine tasting, which cellars are truly worth your time, plus practical tips on how to plan your visit and how long to stay. If you’re building a bigger trip, start with our Tuscany itinerary and Italy Travel Guide.
Montepulciano: At a Glance
LOCATION | Tuscany
BEST FOR | Wine lovers, history enthusiasts, photographers, foodies
DON’T MISS | Underground wine cellars, climbing the clock tower, Temple of San Biagio
HOW LONG | Half a day minimum; full day for wine tastings + meals
NEAREST TOWNS | Pienza (20 min), Montalcino (45 min), Siena (1 hr)
WINE | Vino Nobile di Montepulciano — one of Tuscany’s great reds
OVERNIGHT STAY | Optional; most visit as a day trip from Siena or a Val d’Orcia base
Is Montepulciano Worth Visiting?
Yes, and we’d say that even if you don’t drink wine.
Montepulciano is one of the larger and more rewarding hill towns in southern Tuscany. The main street, Il Corso, winds uphill through a genuinely medieval town center, lined with boutique shops, restaurants, and the occasional glimpse of the Val d’Orcia through a gap in the buildings. Piazza Grande at the top is one of the finest main squares in the region, and the views from the clock tower alone are worth the trip.
That said, wine is the reason most people make the effort to get here, and rightfully so. Vino Nobile di Montepulciano is one of Tuscany’s greatest wines, and Montepulciano is the best place in the world to taste it.
The underground wine cellars are unlike anything else in the region: cavernous, atmospheric, and stocked with bottles that you can taste on the spot. If wine is a priority for you, Montepulciano deserves a full half day at minimum, with time built in for at least one cellar visit and a proper tasting.
If wine isn’t your thing, the town still earns a half day. Climb the clock tower, walk the side streets off Il Corso, visit the Temple of San Biagio below town, and have lunch. You’ll leave satisfied.
Best Things to Do in Montepulciano
1. Stroll the City Streets
Montepulciano is long and narrow. In the north end of town, Porta al Prato marks the entrance into Montepulciano. A tangle of streets runs south, ending near Fortezza Medicea. As you walk into town on Porta al Prato, it is an uphill walk until you reach Piazza Grande.
The main road through town, also called Il Corso, changes names several times as it makes it way through Montepulciano. It starts at Porta al Prato and is called Via di Gracciano, Via di Voltaia, Via dell’Opio, and Via del Poliziano, before ending at Chiesa di Santa Maria dei Servi.
From Il Corso, the side streets lead to viewpoints, shops, wine cellars, and restaurants.
One of the best things to do in Montepulciano is to walk Il Corso and explore these side streets. You never know what you might find, but there is a good chance you’ll come across small restaurants, boutique shops, and quiet corners away from the busier touristy areas.
Il Corso
Il Corso
2. Piazza Grande
Piazza Grande is the main square of Montepulciano. This large, open square is lined with some of the most important buildings in Montepulciano, including Town Hall, the Cathedral of the Assumption, Contucci Palace, Palazzo dei Capitani del Popolo, and the Well of the Grifi and the Lions.
Sitting on Piazza Grande is the Cathedral of Saint Mary of the Assumption. This cathedral may not be as eye-catching as other cathedrals in towns like Siena or Lucca, but it does occupy prime real estate in Piazza Grande. The cathedral was consecrated in 1712 and inside is the Assumption of the Virgin, painted by Taddeo di Bartolo in 1401.
Piazza Grande
Well of the Grifi and the Lions
3. Climb the Clock Tower on Palazzo Comunale
If you have plans to visit Florence, you may notice some similarities between the town hall of Montepulciano (Palazzo Comunale) and the town hall (Palazzo Vecchio) in Florence. Both buildings share an almost identical architectural style. The façade of the Palazzo Comunale dates back to 1424 and was designed by architect Michelozzo.
For one of the best views of Montepulciano, climb to the top of the clock tower on Palazzo Comunale. You have the option to take the stairs all of the way to the top (150 total) or ride the elevator to the terrace and walk the remaining 52 steps to the top.
View from the clock tower
View of the Temple of San Biagio from the clock tower.
One more view from the clock tower.
4. Taste Vino Nobile di Montepulciano
Vino Nobile di Montepulciano is the main wine that is produced in the vineyards near Montepulciano. To be a Nobile di Montepulciano, the wine must be made from a minimum of 70% Sangiovese grapes, and it also contains small amounts of Canaiolo Nero and Mammolo. The wine is aged for at least two years, and at least one year of this needs to be in an oak barrel.
There are numerous places in Montepulciano where you can taste Vino Nobile di Montepulciano, ranging from enotecas (wine shops), restaurants, and underground cellars. More on this next.
We had a nice wine tasting experience at Pulcino Di Matassini Ercolani Gabriella Fattoria (say that three times fast!). This wine shop and restaurant is located on the north end of town. It’s a nice place to end your visit to Montepulciano, if you parked on the north end of town, because if you purchase some wine, you won’t have to carry it far to get back to your car.
Pulcino Di Matassini Ercolani Gabriella Fattoria
5. Visit an Underground Wine Cellar
Visiting an underground wine cellar is one of the best things to do in Montepulciano. Some can be visited on a tour, some on a tour with a tasting, or you can simply do a tasting in the cellar.
De’Ricci Cantine Storiche is one of the most popular and well-known wine cellars in Montepulciano. With high vaulted ceilings, enormous barrels of wine, and even a few statues here and there, this is one to put on your list. For the best experience, book a tour and tasting, which you can do in advance on the official website.
De’Ricci Cantine Storiche
Cantina Contucci is another wine cellar we recommend. We were permitted to walk through the cellar without doing a tasting or tour, so if you quickly want to see the inside of an underground wine cellar, this is one to consider.
Cantina Contucci
Cantina Ercolani, also called Azienda Agricola Ercolani, is another very popular cellar to visit. We have mixed thoughts on this one. The only way to see the underground cellar is on a free tour, which last 20 minutes, and are offered very frequently throughout the day. You learn some of the history of Montepulciano on this tour, which is interesting. The tour ends with a wine tasting, and when we did this, it was a crowded and rushed, and overall it was not a good experience.
Cantina Ercolani
Cantina Ercolani Cellar
6. Visit Fortezza Medicea (& Go Wine Tasting)
This Medici Fortress sits on the south end of Montepulciano. There are no walls to walk or towers to climb, but you can stroll through a botanical garden and go wine tasting.
Inside of the fortress is Enoliteca Consorzio Vino Nobile. It is here that you can taste Vino Nobile di Montepulciano, Rosso di Montepulciano, and Vin Santo di Montepulciano wines.
When you first enter, pick up a “credit card.” This card gets inserted into the wine dispensary and you get charged for each wine you taste (the average cost is about €2 per tasting). The cost of the tasting and the cost of each bottle of wine is listed on the bottles.
As you walk through the shop, you are walking on glass floors and can look down into the excavations of the fortress. Once you have your wine, exit out of the back of the shop, have a seat at one of the tables, and enjoy the view, and the wine, of course.
If you taste anything you like, purchase it on your way out of the shop.
7. Vaduta Panoramica
For one of the best views of the Val d’Orcia countryside, make time for Vaduta Panoramica. This viewpoint looks out over the rolling hills and vineyards below Montepulciano. We visited on our second visit and it’s worth the short detour.
Here’s the view (and here are the GPS coordinates so you know where to find it: 43°05’40.0″N 11°46’51.0″E).
Vaduta Panoramica
8. Visit a Museum
If you want to learn more about Montepulciano, there are a few museums worth mentioning (but if you prefer to sip wine and stroll the city streets, and skip the museums, that’s just fine, too).
The Civic Museum
The Civic Museum is the more substantive of the two, housing Etruscan artifacts and works of art including two altarpieces formerly displayed in Palazzo Comunale. It’s a good complement to the historical context you’ll absorb just by walking the town. For hours and pricing, visit the official website.
Civic Museum
The Torture Museum
It seems like every small town in Tuscany has a Torture Museum, and Montepulciano is no different. For hours and pricing, visit the official website.
9. Temple of San Biagio (Chiesa di San Biagio)
The Temple of San Biagio is a church that was constructed between 1518 and 1548. It is different from many other churches one might see in Tuscany, with its Greek cross plan and central dome. It is an Italian Renaissance masterpiece.
Temple of San Biagio
This church sits just outside of Montepulciano, down the hill from the historic city center. To get here, we drove and parked in the lot next to the church.
There is a small fee to enter the church. For hours and pricing, visit the official website.
10. Take a Tour of Montepulciano
There are several great tours that you can take, including wine tastings, cellar visits, and food tastings.
On this tour, taste the wines of Montepulciano, tour a wine cellar, and learn about the history of winemaking in the area.
This tour includes a wine tasting and lunch in a wine cellar.
In this small group class, learn how to make tiramisu and several pasta dishes.
If you don’t plan on renting a car while in Tuscany, you can visit Montepulciano on a tour. This takes care of your transportation to and from Montepulciano, which can save you a lot of time, since Montepulciano is not easily reachable by public transportation. Here are several tours of Montepulciano that start from nearby towns.
Tours & Tickets
Things to Do in Montepulciano: On a Map
How to Use This Map: Click the tab in the top left corner of the map to see a list of the points of interest and to turn layers on/off. Click the icons on the map to get more information about each point of interest.
To take this map with you, click the star next to the title of the map which adds it to your Google account. Next, within your Google Maps app, select ‘Saved’ and then select ‘Maps’. This map title will now appear in your list.
How Much Time Do You Need in Montepulciano?
To visit the main highlights of Montepulciano, you need about half of a day, or roughly 4 hours, in town. This gives you enough time to stroll the city streets, go shopping, climb the clock tower, go wine tasting at one or two places, and have lunch or dinner. With a full day, you can thoroughly explore Montepulciano and go wine tasting at several different cellars.
Best Time to Visit Montepulciano
The best times to visit Montepulciano are late spring and early fall.
May through mid-June is one of the most beautiful times to be in this part of Tuscany. The Val d’Orcia countryside is at its most photogenic, with fields of vivid green and gold stretching out below the hilltop towns, and the temperatures are comfortable for walking. Crowds are present but manageable compared to the peak summer months.
September through October is our personal recommendation, and the time of year we’d choose again. We visited in October and found it ideal, with cooler temperatures, a more relaxed pace, and the bonus of harvest season. The vineyards around Montepulciano are actively harvesting in late September and early October, which gives the whole area an energy that you won’t find at any other time of year. We stayed at Villa le Prata during harvest and it was one of the highlights of our time in Tuscany.
July and August bring the largest crowds and the hottest temperatures. We visited in July on our first trip and while we still had a memorable experience. A thunderstorm has a way of making any visit unforgettable. However, the heat and the summer crowds are real. If summer is your only option, visit early in the morning before the tour buses arrive and plan for a slower, shadier afternoon.
November through March is the quietest period. Some wine cellars and restaurants reduce their hours or close entirely, and the Val d’Orcia can be grey and cold. That said, if you’re a wine
Helpful Tips for Visiting Montepulciano
To check the weather forecast, we used Meteo Italy and the forecast was relatively accurate. There is also an app that you can download onto your phone.
The town is uphill. Montepulciano runs along a narrow ridge and the main street climbs steadily from Porta al Prato up to Piazza Grande. Wear comfortable shoes and pace yourself, especially on a warm day.
Plan your wine cellar visit in advance. The underground wine cellars are one of the best things to do in Montepulciano, but experiences vary significantly. We’d recommend booking a tour and tasting at De’Ricci Cantine Storiche ahead of time rather than joining a walk-in tour, which can feel rushed. More on this in the wine cellar section below.
End your visit at a wine shop near where you parked. If you’re planning to buy bottles to take home, think about logistics before you start tasting. We made our wine purchases at Pulcino, near the north end of town, so we didn’t have far to carry them back to the car.
Make dinner reservations in advance. The top-rated restaurants in Montepulciano fill up quickly, particularly in summer. If you’re planning to have dinner in town, book ahead.
Where to Eat
Montepulciano has a solid restaurant scene, particularly if you’re looking to pair local food with Vino Nobile.
La Vineria di Montepulciano is one of the most highly rated restaurants in town, known for meat and cheese platters and local pasta dishes, exactly the kind of food that pairs well with a glass of Vino Nobile. L’Altro Cantuccio Ristorante and Rosso Rubino Trattoria are also consistently well reviewed for traditional Tuscan fare. If you’re looking for a special occasion dinner, Le Logge del Vignola holds a Michelin star and is worth booking well in advance.
One food and drink experience we can personally vouch for: the vin santo at Avignonesi, the winery located between Montepulciano and Arezzo. It was unlike anything else we tasted in Tuscany. If you have the chance to try it, don’t pass it up.
As a general rule in this part of Italy: make your dinner reservation before you arrive in town, not after. The best restaurants fill up fast, particularly in summer.
How to Get to Montepulciano
By Train
There are no train stations in Montepulciano. Getting here using the train or bus is complicated and takes quite a bit of time.
If you are traveling by public transportation, it is possible to take a train from Siena to the Montepulciano train station, but this train station is located several kilometers from the historic city center, in Montepulciano stazione. From here, take a bus or taxi into town.
The Chiusi train station, which is farther away from Montepulciano, sits on a major train line, so if you are coming from Rome, Florence, or another Italian city, this is the station for Montepulciano. From here, take a bus to Montepulciano.
By Bus
Buses connect Siena and Montepulciano. You can check the bus timetable here.
By Car
The best way to get to Montepulciano is by rental car.
Here are driving distances and times from nearby destinations:
- Montalcino: 36 km, 45 minutes
- Pienza: 15 km, 20 minutes
- San Quirico d’Orcia: 23 km, 30 minutes
- Siena: 65 k, 1 hour
- Florence: 110 km, 1.5 hours
- Arezzo: 53 km, 55 minutes
Parking in Montepulciano
There are numerous parking lots in Montepulciano, outside of the historic city center.
On our most recent visit, we parked in a parking garage located under the Conad grocery store, just north of the historic city center. There are numerous parking lots (parcheggios) located around the city center. You can mark them on your Google Map before you go, or as you approach Montepulciano, there are signs directing you to the parking lots (P1, P2, etc). Midday, have some patience, because the lots can be full, particularly those closest to the city center.
Things to Do Near Montepulciano
Montepulciano sits in the heart of Val d’Orcia, one of the most scenic corners of Italy and a UNESCO World Heritage landscape. The towns within driving distance of Montepulciano are some of the best in Tuscany and here’s how we’d approach them.
Pienza is the closest and smallest of the nearby hill towns, just 20 minutes away. The main draws are the pecorino cheese, the Renaissance streets, and the views over Val d’Orcia. A visit here can be genuinely quick; a couple of hours is enough, which makes it the easiest town to pair with Montepulciano in a single day.
Montalcino is 45 minutes away and one of our favorite towns in all of Tuscany. It’s smaller and less crowded than Montepulciano, with numerous shops where you can taste Brunello di Montalcino, one of Italy’s greatest wines, and a fortress tower with stunning views over the countryside. If you’re choosing between Montalcino and Montepulciano for a wine-focused stop, honestly, visit both. They offer different wines and a different atmosphere.
San Quirico d’Orcia is a lesser-known but beautiful town in Val d’Orcia, just 30 minutes from Montepulciano. It’s less touristy than Pienza or Montalcino, with a quiet main street, excellent lunch options, and a pace that feels genuinely local. Worth adding if you want to balance the more visited stops with something calmer.
Arezzo is about 55 minutes north of Montepulciano and a different kind of Tuscan town entirely A visit here is less about wine, and more about art, architecture, and the famous Piazza Grande. It’s better suited as a standalone day than a pairing with the Val d’Orcia towns, but if you’re routing through on your way to or from Florence, it’s well worth a stop.
For wine lovers: There are several wonderful vineyards to visit near Montepulciano. We visited Avignonesi, which is located between Montepulciano and Arezzo (try their vin santo…it’s unlike anything else we tasted in Tuscany), but Icario Winery is also highly rated and it is closer to Montepulciano.
Where We Stayed
We spent three nights at Villa le Prata, which is a short drive from Montepulciano and a great home base for exploring Val d’Orcia. At Villa le Prata, we got the experience of staying in a Tuscan villa, which was extra special since the end of September is harvest season. At the villa, we had dinner each night, plus sunset wine tastings and tours of the vineyard.
Staying in a villa is a wonderful experience to have while in Tuscany. There are many villas located in the area, but we chose Villa le Prata since it gets rave reviews, and we have to agree. Staying here was one of our highlights of our time in Tuscany.
Villa le Prata
Frequently Asked Questions
What is Montepulciano known for?
Montepulciano is best known for Vino Nobile di Montepulciano, one of Tuscany’s most celebrated red wines, and the underground wine cellars where you can taste it. But the town has a long and layered history beyond wine. It dates back to the 4th century BC, when the area was inhabited by the Etruscans, who left behind caves and ancient structures that can still be seen today. The medieval town center that visitors explore now was largely built in the 14th century AD. Montepulciano has also appeared in several well-known films, including Under the Tuscan Sun, The Twilight Saga: New Moon, The English Patient, and A Midsummer Night’s Dream — the latter two of which used the town’s streets and architecture as backdrops.
Which is better, Montalcino or Montepulciano?
Montalcino and Montepulciano are similar in that wine tasting is the #1 thing to do. Montalcino is smaller and less touristy, so if you want to tour a town with fewer crowds, we recommend Montalcino. Montepulciano is a larger town with a longer to do list. Both times we were here, it was also more crowded than Montalcino. We really like both towns, but of the two, Montalcino is our favorite.
How much time do you need in Montepulciano?
To explore the streets of Montepulciano, go wine tasting, do a little shopping, climb the clock tower for the view, and have lunch or dinner, plan on spending about a half day (roughly 4 hours) here.
What is Vino Nobile di Montepulciano?
Vino Nobile di Montepulciano is one of Tuscany’s great red wines, produced from vineyards surrounding the town. To carry the Vino Nobile designation, the wine must be made from a minimum of 70% Sangiovese grapes, aged for at least two years with a minimum of one year in oak barrels. The result is a full-bodied, complex red that pairs beautifully with the meat and pasta dishes you’ll find throughout the region. Montepulciano is the best place in the world to taste it and the underground wine cellars in the historic center let you taste directly from the source, often at very reasonable prices.
Plan Your Tuscany Trip
Montepulciano is one of the crown jewels of southern Tuscany, and it pairs beautifully with the rest of the region. If you’re still building your itinerary, our Tuscany itinerary covers how to structure your time across the region, whether you have three days or a full week. For a broader overview of what the region has to offer, our guide to the best things to do in Tuscany is a good place to start.
If you’re combining Montepulciano with nearby towns, as most visitors do, our guides to Pienza and Montalcino will help you plan both stops.
And if you’re still in the early stages of planning your Italy trip, our complete Italy Travel Guide covers everything you need to know.
If you have any questions about the best things to do in Montepulciano, let us know in the comment section below.
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