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Montepulciano is a charming small town in the Tuscan countryside, just a short two-hour drive from Florence. It is known for its old churches, cozy piazzas, and famous variety of wine. There are various things to do in Montepulciano and beautiful sights to see.
That being said, many people venture to Montepulciano to slow down and enjoy the slow pace of things. Enjoying some authentic Tuscan meals and getting lost in the meandering alleyways is enough for many visitors.
No matter your reason for visiting, the hilltop village is well worth a visit and one of the best day trips from Florence.
Here are some of the best things to do, whether you are just visiting as part of a day trip or staying in Montepulciano for a few days.
Montepulciano Travel tips
Location of Montepulciano
Montepulciano is a charming city located in southern Tuscany in the province of Siena. The town sits high on a hill overlooking the Val d’Orcia. Montepulciano is located only 77 miles from Florence and less than an hour’s drive southeast of Siena.
Best Time to Visit
The best months to visit Montepulciano are June and September. These are on the edge of peak tourist season and times of the year when the weather is perfect. During July and August, the city is packed with tourists. They are also the most humid months of the year.
Montepulciano’s History
The city was said to be founded by Lars Porsena of Clusium, the Etruscan Kind, in the 4th century B.C. Montepulciano was built first as a military camp and later taken over by the Lombards.
The city continued to see lots of turmoil as it competed with others in the area for power. Siena was one nearby city that was set on capturing Montepulciano for its land. Florence was another city that aimed to control Montepulciano and, at one point, took over the city.
The control of Florence in 1511 ended up being a positive thing for the city. During the Renaissance period, the town was a place where many artists came for inspiration. As a result, the town grew in population and size, and the buildings closely resembled those in Florence.
Today, thousands visit the city each year to experience the area’s history and indulge in the world-famous wine, Vino di Nobile di Montepulciano.
How to Get to Montepulciano
You can see Montepulciano as part of a day trip from Florence by train from Florence. The fast train takes about 1 hour and 35 minutes, with the first train running at 5:45 in the morning. A day trip could be a good option if you are short on time or want to explore the town.
The station is outside of the town, so you will need to get a taxi or wait for the bus to take you the rest of the way.
You can get to Montepulciano directly by bus from Florence and other nearby cities. However, it will take much longer to reach the town. If you are interested in purchasing bus tickets to Montepulciano, Omio is a wonderful website to researching bus schedules and fares.
I recommend renting a car and visiting the Tuscan towns surrounding Montepulciano, such as Siena. There are many unique places to see and renting a car allows you to take your time exploring the countryside.
Check out car rental rates and availability
Another great thing about renting a car is that you can venture outside Montepulciano without joining a tour. There are numerous sites and vineyards just outside of the city that you can get to by car.
One thing to know is that the city center is closed to cars. However, there is a large parking lot on the outskirts of the town. It is relatively inexpensive to park your car here and a short walk into town.
Lastly, you can get to Montepulciano as part of a day tour. Several tours from Florence will take you to the city and the surrounding area. In addition, some excursions include a stop in Siena along the way.
Explore some popular day tours from Florence.
Where to Stay in Montepulciano
Accommodations Inside Montepulciano
There are many cozy accommodations in Montepulciano. If it is your first time visiting the city, stay in or around the center of town. Especially if you do not have a car, staying in town makes getting around easy since you can walk to anything within the city walls.
For the ultimate luxury experience, stay at this historic Palazzo Nobile di San Donate. Your suite is furnished with beautiful antique pieces and adorned with 17-century frescoes. Best of all, you have private views of Val d’Orcia from your suite.
Right in the heart of the city is the Il Tosco hotel. The 15th-century building has been turned into suites with traditional furnishing, beautifully exposed beams, and spacious communal living areas. Best of all, you are just steps from the best shops and restaurants in Montepulciano.
Accommodations Outside Montepulciano
Another option is to stay on the outskirts of town. There are many cozy rentals and wine hotels on the outskirts of town. Staying outside the city is an excellent option if you have your own transportation and would rather have a quieter place to stay.
The beautiful Terra Antica Resort and Winery is just over 6 miles from Montepulciano. The modern rooms come with everything you need, including a public pool, large kitchen and living areas, and spectacular city views in the distance.
Agriturismo San Martino is the perfect accommodation for a quiet escape in the Tuscan countryside. Located only 2,650 feet from the city, this charming hotel offers a mix of traditional and modern amenities, a natural swimming pool, and cozy outdoor seating areas with views of Montepulciano and nearby vineyards.
The Best Things to do in Montepulciano
Relax at Piazza Grande
Piazza Grande is the main square in the center of Montepulciano. The area has charming cafes and some of the city’s most important buildings. The square dates back to the 1300s and is where you will find many top attractions.
A fun fact about the Piazza Grande is that it has been used as a filming location several times. Many people have seen it in the movie New Moon, part of the Twilight series. The piazza has also appeared several times in the T.V. series Medici.
One of the prettiest parts of Piazza Grande is Il Pozzo dei Grifi e de Leon. This beautiful fountain sits on the piazza’s edge and is decorated with lions and griffins. If you look closely, you can see the Medici coat of Arms. The wealthy family of bankers greatly influenced Italy for around 300 years.
Go Shopping Along Il Corso
Il Corso is the main street in Montepulciano. Since many names know it, some people need clarification about where to find it. Some of the terms you may hear people refer to are Via di Gracciano and Via di Voltaire. They are all talking about the same place!
You should not have too much trouble finding it, look for the section of shops and restaurants. You can find anything from inexpensive souvenirs to impressive leather goods on Il Corso.
The lively street is also a great place to stop for something to eat and an excellent location for people-watching. The buildings along the street are also worth noticing. Many were built back during the renaissance period.
What better way to explore the city than by foot? Join this culinary walking tour of Montepulciano and indulge in some of the region’s best food and wine along this way.
Enter Through Porta al Prato
When you go to Montepulciano, chances are you may stroll through the Porta al Prato. It is one of the gates that lead into town. The large archway is part of the town’s fortification dating back to the 14th century,
Porta al Prato leads you to Il Corso, the town’s main street. A quick 10-minute stroll up the road will take you to the center of town, known as the Piazza Grande. The piazza is where you will find several of Montepulciano’s top attractions.
Fortress of Montepulciano
The Fortress of Montepulciano, also known as the Medici Fortress, has some of the best views in Montepulciano. You can even see the magnificent Church of San Biagio from here.
It was built in the mid-13th century as a military fortress at the city’s highest point. However, the structure you see now is partially original. The defense was destroyed numerous times over the centuries due to battles. Siena and Florence were town competitors who both wanted control over the city.
A Medici architect by the name of Antonio da Sangallo il Vecchio was one of the people who helped restore the fortress. For that reason, many know it as the Medici Fortress.
It has gone through numerous other renovations and is currently used for study abroad programs and exhibitions. The fortress is open to visitors and has a delightful wine bar on its terrace that looks over Val d’Orica.
After you have spent some time walking around, enjoy a wine tasting on the terrace and enjoy the views of the countryside.
Wine Tasting & Vino di Nobile di Montepulciano
Wine tasting is one of the best things to do in Montepulciano. Tuscany has several delicious wines, but one of the most famous is Vino die Nobile. You can taste this spectacular wine in many different ways, including joining a wine tour.
The red wine is made mainly with Sangiovese grapes. It is a medium-bodied, dry wine with fruity flavors. The wine is aged in large oak barrels for a minimum of 24 months. On top of the aging period, the wine must be at least 70% Sangiovese grape.
Since the classic wine comes locally from the region, you can find it at any wine bar or restaurant in Montepulciano.
One of the best places to go wine tasting is Enoteca Borgo Divino. The wine shop is also where you can find some delicious regional produce, such as pecorino cheese and olive oil.
Another great wine bar in Montepulciano is La Bottega Del Nobile. You can try over 60 wines here and an assortment of snacks.
If you want to visit several wineries, join a tour. Indulge in the best Brunello and Vino di Nobile wines with the help of a guide.
Palazzo Contucci
The Palazzo Contucci is another building constructed by the architect Antonio da Sangallo il Vecchio. It was built in the 16th century and includes influences of Renaissance architecture. Like several other important buildings in Montepulciano, it lines the Palazzo Grande in the center of town.
The Palazzo Contucci is a large residence that was the home of the famous winemakers. It was even home to influential figures like Pope Giulio III and Grand Duke Ferdinand. Now, the Palazzo Contucci is used for unique vacation rentals.
Fun Fact: The large cellar of the Contucci Winery run underneath the palazzo.
Walk to the Church of the Madonna San Biagio
The Church of San Biagio sits below the town of Montepulciano on the side of the hill. It is a short 20-minute walk to get to, with fantastic countryside views along the way.
The church was built in the 16th century, starting in 1518, by Antonio da Sangallo the Elder. What makes the church unique is its light-colored exterior and dome.
The interior of the church is fascinating to see. The intricate design on the ceilings, stained glass windows, and Renaissance art collection.
Although you can see it from many different places around town, it is one of the best things to see in Montepulciano and worth taking the trip and experiencing up close and personal.
Climb the Palazzo Comunale
Another great place to see the Tuscan countryside is the top of the Palazzo Comunale. Cosimo I de Medici ordered the tower’s construction during their time of power in Florence.
Climbing to the top of the bell tower will give you panoramic views of the city and the surrounding area.
If you do not mind the climb up the 68 steps to the top, the palazzo’s bell tower gives you the highest viewing point in the city. However, if heights are not for you, the city hall has a terrace you can walk to instead. The terrace and bell tower are €5 to visit and are open daily from 10:00 am to 6:00 pm.
Visit the Museo Civico
You can find the museum in the lovely 14th-century Palazzo Neri Orselli. The art museum has four floors of archeological finds, furnishings, terracotta collections, and art gallery. The museum also has a beautiful courtyard and loggia for visitors.
The hours of operation change depending on the time of the year. During April and October, you can visit every day except Tuesday from 10:00 am to 7:00 pm. For updated prices, exhibits, and hours check out their website.
Val d’Orcia and Monticchiello
Many people have seen pictures of Val d’Orcia, but they need to know what it is. The picturesque valley is known for its winding path that cuts through the rolling fields of Tuscany.
Sitting in a lush valley with large cypress trees lining the road on each side, Val d’Orcia is one of the most beautiful landscapes in the region.
The valley is a UNESCO World Heritage Site and home to the small Tuscan town of Monticchiello. The delightful village is a beautiful place to walk around and grab lunch. Ristorante Daria and Osteria La Porta are two of the best places to stop.
Although you can visit any time of day, sunset is one of the best photo opportunities. At that time of day, the sun sets over the hills in the background. Val d’Orcia is one of the many places near Montepulciano you need to stop by and see.
Explore Val d’Orcia as part of a tour. This popular tour takes you around to some famous filming locations in the area. Some films such as The Gladiator and New Moon were filmed here. After touring the various locations, your guide will take you to an underground cellar for a wine tasting.
Tour the Wine Caves
Tuscany is known for producing some of the world’s best wines. So if you are a wine lover, this is your top destination. You can reach many of the Tuscan vineyards from Montepulciano.
One of the best things about these wine tours is that many cellars are underground below the city. The maze of tunnels winds its way beneath the town and is open to visitors as part of a tour. Tours are a great way to learn more about the wines and go behind the scenes about how they produce them.
During your tour, you will learn about the town’s history and winemaking process. But, most importantly, you can taste some of the best wines in the world.
Best Wineries in Montepulciano
- Gattavecchi is one of the best wineries in Montepulciano. You can partake in wine and olive oil tasting and stay for a delicious Tuscan meal. There are three levels of wine tasting available starting at €30. The tasting also includes bread, cold cuts, and cheeses.
- De Ricci Winery is another fantastic winery inside the city. The winery belonged to the prestigious Ricci family, who lived in Montepulciano in the 12th century. They offer tasting and tours of the wine cellars nicknamed “the Cathedral de Vino”. The cellars alone are sure to impress. After your tour, enjoy a tasting on the terrace with some of the best views of Tuscany.
- Contucci Winery is one of the oldest in Tuscany, open for over 1000 years, and very popular. It is also situated in the city’s main square, making it easily accessible. One of the best parts of visiting Contucci is its extensive underground cellars.
Wander Around the Old City of Montepulciano
As you approach Montepulciano from below, the view is spectacular, but the medieval streets are even more enjoyable.
The city is full of little alleyways that curve up and down through the town. With so many old budlings lining both sides of the road, it is easy to forget about doing anything else and spend the afternoon exploring.
Many cobblestones roads are pedestrian streets filled with restaurants, colorful homes, and hidden surprises at every turn.
You can reach the Old City at either of the two main gates inside the town. However, I recommend accessing it from Porta al Prato.
Visit the Churches of Montepulciano
Like many Italian cities, you will find a variety of beautiful churches. However, some of the most exquisite ones inside the city walks are:
Cathedral of Santa Maria Assunta
The old duomo sits in the Piazza Grande (pictured above). It is also known as the Duomo di Montepulciano. The church was built in 1698 and took under 90 years to complete.
Sant’Agostino Church
The old church was founded in 1285 but has since gone through numerous restorations. You can recognize the building by its white marble exterior and large decorative wood door.
After you have explored the church, check out the Torre del Pulcinella. The tower is at the entrance of the old city next to the Church of Sant’Agostino. The building is pretty easy to spot due to the large Pulcinella on its top. The Pulcinella is a puppet character created in Naples.
Church of Sant’Agness
Another beautiful church in Montepulciano is the Church of Sant’Agneses. The church was built in the 13th century and decorated with a large gothic doorway and frescos. This church is just outside the city walls, near the Porta al Prato.
Enjoy Views of the Countryside
Since Montepulciano sits high on a hilltop, you can get spectacular countryside views. There are several great locations for you to go to get those uninterrupted views.
One of the best places to see 360-degree views of the city and countryside is the Palazzo Comunale due to its high location on the hill. If you are lucky, you can see some nearby cities in the distance.
Another excellent place is the Fortress of Montepulciano, also known as the Medici Fortress. Many people enjoy coming here because there is a large terrace where you can sit and enjoy a glass of wine as you peer down on the rolling hills below.
Unwind in a Thermal Bath
Not many people know this, but Tuscany is home to many thermal baths. One of the closest to the city is the Terme di Montepulciano Spa. Thermal baths are rich in magnesium and bicarbonates and are a great way to destress and detoxify. The property also has an indoor Moonlight Cave with a cozy hydromassage pool built into the rock.
One of the best Thermal Baths near Montepulciano is Bagno Vignoni. It is one of the oldest in the area, with a large pool in the center of the square, used centuries ago by the Romans. Since it is located close to Pienza in Val d’Orcia, you can get to eat as part of a day tour.
After you relax in the therapeutic waters, have a romantic dinner in town or explore more of the surrounding landscape.
Indulge in Some Local Cuisine
There are some delicious restaurants in the town. One of the things to do in Montepulciano is trying their local dishes. The city is known for its pasta dish, pici all bricole, or “pici”. The pasta dish is made with thick handmade spaghetti and topped with either tomato sauce or sauteed breadcrumbs.
Pecorini di Pienza is another popular local product. The unique cheese is produced in the nearby town of Pienza using sheep’s milk. Make sure to try some with a slice of Tuscan Bread.
Unlike most bread, Tuscan bread does not have salt. This unique way of making bread has been around for centuries due to salt shipments being blocked by the rival city of Pisa. Although salt is now plentiful in the region, bread is still made using this age-old recipe.
One of the best places in Montepulciano to taste the local cuisine is Osteria dell’Acquacheta. The simple dishes here are flavorful and made with only local ingredients.
For that reason, the menu changes weekly based on the produce available. The owner even uses a handwritten menu of the daily specials. Osteria dell’Acquacheta is a unique place that makes you feel right at home.
La Bottega del Nobile is another excellent place to eat. It is located in the cellars of Palazzo Avignonesi and is both a delicious restaurant and wine bar. They pride themselves on their traditional dishes with a twist. For a romantic evening, you may choose to eat in the historic cellars or outside.
Stop by their market if you happen to be in Montepulciano on a Thursday. You can find some outstanding produce here!
Day Trips from Montepulciano
One of the reasons to stay in Montepulciano is that it makes an excellent base for exploring Tuscany. If you have a few days to stay in the region, I highly recommend it.
Siena
One of my personal favorite towns in Tuscany is Siena. Siena is a larger city in the Tuscany region and one of the most visited besides Florence. Florence and Siena were rivals for centuries, adding to the city’s intrigue. Siena is full of beautiful buildings, small pedestrian streets, and open piazzas.
While in Siena, spend some time lounging on the Piazza di Campo, exploring the beautiful churches, and climbing the Duomo for spectacular countryside views.
We visited to experience the annual Palio race and fell in love with the town. This traditional race has been taking place for centuries. If you want to learn more about the Palio, my post covers everything you need to know about the traditional event.
You can also visit Montepulciano as part of a day trip from Siena. The guided tour includes transportation to several villages, lunch, and a wine tasting.
Pienza
Pienza is a perfect day trip from Montepulciano since it is only 20 minutes away. The UNESCO World Heritage town is known for its delicious pecorino cheese. It is also a wonderful Renaissance town that has remained pretty untouched over the centuries.
While in Pienza, visit the large Piazza Pio II, Cettedrale dell’Assunta, and Palazzo Piccolomini. When you get hungry, stop by a local shop for their world-famous Pecorino of Pizza cheese.
Once you have explored the Renaissance city, continue to the nearby village of Montalcino before heading back to Montepulciano.
Montalcino
The medieval city of Montalcino is another great day trip from Montepulciano. The fortified town looks like it came out of a fairy tale and has stayed almost unchanged since the 16th century.
It is where you will find the delicious Brunello wines, another Tuscan delicacy. The Brunello was invented in the 1880s and has become one of the world’s most coveted varieties of wine.
Montalcino is a short 45-minute drive and is the perfect place to experience some of Tuscany’s vineyards.
San Gimignano
San Gimignano is another magical city in the heart of Tuscany. Many people come here as part of a wine-tasting tour. The charming town is high on top of a hill overlooking the lush countryside. Enjoy strolling around the cozy streets and visiting the many boutiques and cafes while you are there.
If you visit on a Thursday, San Gimignano hosts a large market in the town’s main piazza. Here you can buy fresh produce and other Tuscan delicacies. Other activities include climbing the Torre Grossa, relaxing at the Piazza del Duomo, and sampling the local foods and wines.
You can visit three of these cities as part of a tour. Want a private tour instead? This nine-hour private tour takes you to Montalcino, Pienza, and Montepulciano and includes a wine tasting at a local winery.
Aren’t able to stay in Montepulciano? Not a problem. Many of these locations are great day trips from Florence as well.
Conclusion
Montepulciano is a charming hilltop city in Tuscany with many amazing things to do. It is a popular day trip from Florence an a base for exploration around Val d’Orcia. Know of some other great things to do in Montepulciano? I’d love to hear from you!
Enjoyed this post? Here are some other Italian destinations!
Florence
- The 8 Best Day Trips from Florence
- Visit Florence Italy: Best Places to See, Stay, and Eat
- Travel Guide: How to Spend 3 Days in Florence
- Florence vs. Rome – A Detailed City Comparison
Rome
- 125 Captivating Rome Quotes to Inspire You
- Rome Travel Guide: How to Plan the Perfect Trip
- Travel Guide: How to Spend 3 Days in Rome
- Visit Rome on a Budget: Tips and Free Attractions
Tuscany
Lake Como
- Three Days In Lake Como Itinerary
- Top 12 Best Things To Do in Lake Como
- Visit Villa del Balbianello – Lake Como’s Most Beautiful Villa
Other Italy Posts
- 20 Most Beautiful Cities in Italy You Need to Visit
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- 30 Traditional Italian Foods to Try in Italy
Travel Planning Resources
BOOK YOUR FLIGHT | Skyscanner is the top search engine for finding and booking flights. They price check over 1,200 travel sites to help you find the best prices.
VIEW ACCOMMODATIONS | For booking hotels and vacation rentals Booking.com is a top resource . They offer some of the cheapest rates and different payment options.
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- Rental Car: RentalCars.com is my go-to site when booking rentals. They work with 900 companies worldwide to help you find the best car for your needs and budget.
- Trains: Rail Europe is the leading company in Europe for train travel in Europe. They help you easily book passage by looking at routes, timetables, and prices for 50 different train companies.
- Bus: Omio is an easy website to use for booking train and bus tickets. Similar to Skyscanner, the website looks at hundreds of transport companies to get you the best deals.
SCHEDULE YOUR TOURS | There are many top companies available in Europe. Get Your Guide is one of the best sites for tours, excursions, and activities. Viator is another terrific website for all types of experiences.
GET TRAVEL INSURANCE | Having travel insurance is always a good idea. World Nomads is one of the top travel insurance companies. It will cover you if you must cancel your trip or if something unexpected happens.
Check out the resource page for additional travel planning resources.
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