14 Fun Things to Do in Montepulciano Italy On Your First Visit

Montepulciano is a fairy tale town in Tuscany Italy that every traveler will love. The ancient streets wind their way up the hill, leading to epic viewpoints, world-class restaurants, and some of the best wine in Italy. So what are the most fun things to do in Montepulciano on your first visit? Join us to find out!

How to Get to Montepulciano

The first thing to know is how to actually get to Montepulciano Italy. Luckily, there are several airports that are within a reasonable distance. Perugia and Florence both have airports and are about an hour and a half drive to the small town in Southern Tuscany. 

We ended up flying into Pisa and taking the 2.5 hour bus ride to Montepulciano. While it would’ve have been much easier with a rental car, we knew we wouldn’t use it as much once we got there.

Will you be including Montepulciano in a longer Tuscany itinerary? Then you may want to consider renting a vehicle. Check out Discover Cars to find the best deals and compare different companies.

Our Montepulciano Italy Story

We’d been to Italy several times before, but somehow Tuscany had escaped us. So naturally, we jumped at the opportunity when we found a one-month apartment in Montepulciano.

Even though we visited in the peak season of July, the crowds were not crazy as we anticipated. Most tourists were actually on day trips coming for the afternoon. This meant we had the mornings and evenings mostly to ourselves.

This Tuscan town was everything we expected it to be and more. It was also a great home base for exploring more of beautiful Val D’orcia. Here are 14 of our favorite things to do in Montepulciano Italy!

→ Planning a day trip to Montepulciano Italy? Check out the popular daily tours from Rome, Florence and Siena.

14 Things to do in Montepulciano Italy

1. Montepulciano Wine Tasting 

Okay, we have to start out with the most obvious one. If you didn’t know already, Montepulciano is in the heart of Italy’s wine country. Some of the best vineyards in the world are found in this area of Tuscany, and wine lovers travel from far and wide to get a taste.

An amazing part about wine in Montepulciano is that many of the local vineyards have storefronts right in town. From the moment you walk through the historic Porta al Prato gate, you can stop in for a tasting, buy your favorite bottles, and even ship some home.

→ 7 Best Tips for Visiting the Famous Wineries in Montepulciano Italy

2. Explore the Medieval Streets

One of the most fun things to do in Montepulciano Italy is to walk its beautiful streets. It’s easy to see the influence over centuries in its fortress-like design in the hills of Tuscany. Simply strolling through the ancient city walls and Renaissance architecture will blow you away.

However, know that it isn’t a walk in the park! Montepulciano is basically one big steep hill. Be prepared for this in many of the nearby hilltop towns and bring some good walking shoes.

Let your imagination wander as you climb in elevation through the medieval town. Stop into the shops, sample local products, and have a cappuccino at one of the fantastic views! Montepulciano is quintessential Tuscany in every sense.

3. Stay Inside the Montepulciano City Walls

You’ll be happy to know that there are plenty of great places to stay right in the old town of Montepulciano Italy. Many of the accommodations are housed inside historical buildings dating back hundreds of years.

Of course, they have been upgraded with modern amenities like wifi and air conditioning. You will also find spots with amazing views of the Italian countryside.

Below of a few of our favorite hotels within the historic center. Looking for something with a pool or the Tuscan villa of your dreams? There are also plenty of options just outside of town!

Ultra Luxury – Palazzo Nobile di San Donato – Stay in a Renaissance building in the heart of Montepulciano. The beautiful suites include modern amenities with world-class art adorning the walls. 

Bed & Breakfast – Il Tosco – This 15th century property is just a short walk to the main square. Enjoy a delicious breakfast and private parking on site. 

Bed & Breakfast – Meublé il Riccio – Have a traditional Italian experience along with some of the best views in town from your patio or balcony. 

Guest House – Via Di Gracciano – Perfect base in the center of town with spacious rooms, and walking distance to all the Montepulciano wineries.

Studio Apartment – ManillaHouse – Apartments with full kitchens and living areas. A great alternative to hotels in Montepulciano if this is more your style.

4. Hang Out in Piazza Grande

In the heart of Montepulciano sits the large square of Piazza Grande. This is the site of many concerts and musical performances throughout the year.

It’s here that you will also see the finest buildings in Montepulciano Tuscany designed by Italy’s best architects. The Florentine influence can be seen right away with the stunning cathedral being an almost exact replica of the famous Palazzo della Signoria.

Other architectural wonders include the Cathedral of the Assumption, Well of the Grifi and the Lions, Palazzo Comunale, and Palazzo Contucci. Grab a drink at Ristorante ai 4 Venti or Bar Gelateria Duomo and enjoy the picturesque square. 

5. Enjoy a Traditional Tuscan Meal

This region of Tuscany is full of delicious specialties, all of which you can try in Montepulciano. The first pasta you should taste is the pici alle briciole. This is the popular pici pasta with traditional Montepulciano ingredients of breadcrumbs, chili, and garlic.

After that, move on to several kinds of meats prepared beautifully at the local restaurants. Chianina steak may be the king of them all, but don’t miss out on the rabbit, goose, and other delicacies on your trip. Also, don’t forget about local cheeses, pizza, and plenty of the famous wine! 

Below are some of our favorite restaurants we tried in Montepulciano Italy. However, there are so many others that are just waiting to be discovered.

• La Vineria di Montepulciano
• La Taverna di San Giuseppe
• Osteria di Casa Chianti
• Panineria Al Vicolino
• Pizza E Cucina da Linda

6. Admire the Magnificent Views of Montepulciano Italy

Montepulciano is has spectacular views everywhere you look! The “walking” we described earlier is honestly more of a hike up the steep and winding city streets. The good news is the higher you get up into town the more scenic the views become.

Seemingly around every corner is another epic lookout over the rolling hills of Tuscany. One of our favorites is near the top of the hill on a back street just behind Piazza Grande. Make sure to have your camera ready for this one.

7. Walk to the San Biagio Church

Just below the walls of town is one of the most beautiful Tuscany churches of the Renaissance era. Known as the Temple of San Biagio, this enormous place of worship was built in the early 16th century.

The way it towers over you is certainly magical. Still, the best view may be from afar with the endless vineyards in the background.

You can walk straight down from the walls of Montepulciano in just 5 minutes to get here. If you’re coming from the main entrance, you will pass through a row of large cypress trees leading to the fantastic church. 

8. Go on a Hike From Montepulciano 

While there are so many things to do in Montepulciano, don’t miss out on the hikes just outside of town. Some of our best days were spent on the hiking trails through the surrounding hills. Many of them connect to other gorgeous towns with history dating to the Middle Ages.

One of our favorites was the 7km trail (each way) goes to the small village of Montefollonico. The path is more like a wide dirt road, but beware! It does have some pretty serious ups and downs. 

→ Fun Tuscany Hike from Montepulciano to Montefollonico Italy

9. Montepulciano Thursday Market 

Sometimes Montepulciano felt like one big market to us. Yet, there is an official farmers market held every Thursday behind the main bus stop. The Thursday morning market is a mix of clothing, local products, fruits, and fresh produce. 

However, the star of the show has to be the porchetta. This is a special Italian stuffed pork roast which found in the heart of Tuscany. 

At the Montepulciano Thursday Market, there are a few different stands selling this delicious treat. Get it sliced on a panini or buy your own stack of porchetta to bring with you.

10. Take an Electric City Tour 

Not up for the steep walking through the streets of town? Don’t worry! There’s another perfect way for you to get to some of the best things to do in Montepulciano Italy. There is a fun tour available that can take you to a handful of different sites around the town. 

While you may see these popular red cars zipping around the streets, you definitely won’t hear them. That’s because the city tour is run with completely electric vehicles. This is also great idea for the elderly travelers or families with young kids.

11. Visit the Montepulciano Museum

Known as Museo Civico, this is the premier art gallery of Montepulciano Italy. The building itself is a wonder as it’s one of the towns rare examples of Sienese architecture. 

Here you will find artifacts on display and learn all about the history of Montepulciano Italy. They date back to the Etruscan and Roman periods along with many incredible sculptures and paintings from the last few centuries. 

One of the most prized works here is a 19th century Caravaggio titled the “Portrait of a Gentleman.” If you have the stomach for it, you can also visit the Medieval Tortue Museum of Montepulciano. Obviously, this museum isn’t for everyone.

12. Attend a Festival in Montepulciano Italy

If you’re lucky enough to be in Montepulciano during the warmer months you may be treated to a festival! They’re typically centered around music, food, and sports, with an emphasis on the culture of this special part of Italy. 

In July, we got to attend the Cantiere Internazionale D’Arte and it was one of the highlights of our visit! Be sure to check the calendar and even think about to visit Montepulciano around a happening festival. 

13. Watch the Montepulciano Tuscany Sunset

Ah yes… That magical time of day! Watching the sunset with a wonderful view is one of the best things to do in Montepulciano, and just another reason to spend the night in town. 

Watching the colors change in the sky as you sip on a fine wine is pure heaven. Take advantage of the viewpoints around town and find your own special place to take in the sunset. 

14. Day Trip From Montepulciano 

There are so many great day trips to take from Montepulciano Tuscany! We really enjoyed using it as our home base for the month. Even without a rental car, we were able to see so many other beautiful historic towns in the area. 

One of our favorite days was when we took the hop on hop off Tuscany bus to nearby Lake Trasimeno. Here we visited the bustling mountain town of Cortona and the stunning Castiglione del Lago. From Montepulciano you can easily get to cities like Siena, Pienza, Florence, or even Rome! 

Have any questions about this article or want to share your own favorite things to do in Montepulciano Italy? Leave us a comment below! 

Safe Travels,
Brigitte & Jake

Where in the world are we? Follow our daily adventures on Instagram @nothingfamiliar! 

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Italy Travel Planning 

Explore Italy: 15 Things to do Venice – Milan Cathedral Rooftop – Milan Canals – Bologna Portico di San Luca – Bologna Street Food

 Flights: We always check Skyscanner and Kayak to search for cheap flights. That’s how we got from Rome to Venice for under $30 USD!

 Accommodation: Compare multiple sites to get to the best deal such as Booking.com and Agoda! Also,  Hostelworld should be your go-to source if you’re traveling on a budget. 

Rental Car: We use Discover Cars to explore when traveling. Consider renting a car in one city and dropping it off in another for an epic Italian road trip! 

 Tours: Check out Get Your Guide for thousands of activities around the world. Book a Florence winery tour, Capri Boat trip or street food tour with a local guide in Rome! 

 Travel Insurance: Never travel abroad without protection! We’ve been using SafetyWing for the last few years on the road and they are there when we need them.

 Packing Lists: Find all the inspiration you need with our Amazon packing lists. Including our electronics and camera gear, must-have medical items, and long flight essentials! 

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