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!
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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 day-trippers coming for the afternoon which meant we had the mornings and evenings mostly to ourselves!
This town was everything we expected it to be and more. It was also a great home base for exploring more of beautiful Tuscany. Here are 14 of our favorite things to do in Montepulciano Italy!
→ If you plan to do a day trip to Montepulciano Italy there are popular tours that run daily 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 wine country! Some of the best wine in the world is found right in this area of Tuscany, and people travel from far and wide to taste it.
The best part about wine in Montepulciano is that many of the local vineyards have storefronts right in town. So while walking through the beautiful streets you can stop in for a tasting, buy your favorite bottles, and even ship some home if you’d like.
→ 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 historic 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 is so amazing!
However, know that it isn’t a walk in the park. Montepulciano is basically one big steep hill! Be prepared for that 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 with a view! Montepulciano is true Tuscany in every sense.
3. Stay Inside the City Walls
You’ll be happy to find out that there are plenty of wonderful places to stay right in Montepulciano Italy. In fact, 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 places with views of the glorious Italian countryside.
Below of a few of our favorite hotels within the ancient city walls. If you’re looking for something with a pool or the Tuscan villa of your dreams, there is also plenty of options just outside of town!
Ultra Luxury – Palazzo Nobile di San Donato – Stay in a historical 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 location 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. Visit Piazza Grande
In the heart of Montepulciano, you will find 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 building works 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 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, chile, 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 wine! Below are some of our favorite restaurants we tried in Montepulciano Italy. However, there are so many others that you are sure to love!
- La Vineria di Montepulciano
- La Taverna di San Giuseppe
- Osteria di Casa Chianti
- Panineria Al Vicolino
- Pizza E Cucina da Linda
6. Admire the Views of Montepulciano Tuscany
One thing to know about Montepulciano is there are amazing views everywhere you look! The “walking” we described earlier through town is honestly more of a hike up the steep and winding roads. The good news is though, the higher you get up into town the more scenic the views are!
Seemingly around every corner is another epic viewpoint of the rolling hills of Tuscany. One of our favorites is near the top of town on a back street just behind Piazza Grande. Make sure to have your camera ready for this one!
7. Visit 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 magnificent structure was built in the early 16th century.
The way it towers over you is certainly magical. However, 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 and be here. If coming from around the other side you will pass through a row of massive cypress trees leading to the fantastic church.
8. Epic Montepulciano Hiking Trails
If you have multiple days as we did there are so many things to do in Montepulciano outside of town. Some of our best days were spent on the hiking trails that go through the rolling hills of Tuscany. Many of them will to other historic medieval towns.
If you have the chance, 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 its ups and downs.
→ Fun Tuscany Hike from Montepulciano to Montefollonico Italy
9. Montepulciano Thursday Market
To us, Montepulciano sometimes felt like one big market! Yet, there is a real live 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! Porchetta is a special Italian pork roast, stuffed, and found particularly in Tuscany. At the Montepulciano Thursday Market, there are a few different stands selling this delicious treat! Get it on a panini to-go or buy your own stack of porchetta to bring home 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 around Montepulciano. 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 option is also a great idea for the elderly or families with young kids because the town streets are so steep.
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 rare examples in the town of Sienese architecture. Here you will find rare artifacts from 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 one isn’t for everyone!
12. Attend a Festival
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 all-around 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 planning around a festival in Montepulciano Tuscany.
13. Watch the Montepulciano Italy Sunset
Ah yes… That magical time of day! Watching the sunset 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 delicious red 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 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!
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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Thank you so much for this info!
You’re very welcome 😊