The terracotta rooftops huddled Tetris-like on the limestone ridgeline. The rust-red quickly melted to green as the valley fell away and verdant vine-wrapped hills were revealed. As we wound around the tight bends, guided by perfectly formed cypress trees we edged past cars, trucks, and even the occasional sedate tractor as the anticipation brewed. The mountain-top medieval town felt both familiar and enticingly new and we couldn’t wait to uncover the many things to do in Montepulciano.
Breathtaking views across the valley from the Montepulciano town walls. | © Skye Gilkeson
Things to Do in Montepulciano
Contents
Getting to Montepulciano
- Getting to Montepulciano is possible from any of the major gateways to Tuscany. Like us, it’s likely you will fly into one of Rome‘s airports and travel on from there. There are also airports in Pisa, Perugia, and Florence. Click to search for flights to Italy.
- From Rome, you can hire a car, catch a train or bus, organize a transfer through your hotel or BnB, or book a Montepulciano wine tour (should you only have a day).
- If you are arriving by train, be aware that the train station isn’t in the town center, nor is it within walking distance, so you will have to catch the local bus up the hill or arrange a hotel transfer.
- Rome to Montepulciano takes about 2.5 hours by car. I highly recommend you hire a car in Tuscany (click to search car rental prices here). It will allow you to reach Montepulciano easily and also to take day trips from Montepulciano if you have a little extra time. If you are driving, simply park near the Fortress or one of the car parks near the top of town, wander down through the streets, and catch the bus back up to the top. For obvious reasons, most of the tours around Montepulciano are walking tours, so check those specific details before you book.
- From Florence to Montepulciano, it’s just a 1.5-hour drive. So, a Montepulciano day trip is very easily added to your Tuscany itinerary, if you are short on time. There are also a number of other stunning Renaissance towns within a short drive from Montepulciano, so spend a week in Tuscany if you can.
- It’s important to note that at 600 meters above sea level and clinging to a limestone ridge, Montepulciano is known for its very steep street so it can be difficult to walk around Montepulciano streets. If you are not particularly fit or you have mobility problems, there is a little red public tourist bus that runs from the bottom of town (near Porta delle Farine) to the top of town near Piazza Grande. You will find red sign-posted stops around the town with one right at Porta Della Farine itself.
Montalcino vs Montepulciano
It really is hard to compare Montepulciano and Montalcino because they both have beautiful attractions. But, they are both stunning, quaint, and historic hilltop towns with delicious dining options and wonderful wine.
If time is a factor and you plan to travel to Florence, Lucca, Milan, or Rome, Montepulciano is slightly closer. If you are keen to see Siena, Montalcino will cut off a bit of time (but really only a few minutes).
We stayed in Montepulciano and went for a wander and ate lunch in Montalcino with a glass of their famous Sangiovese, of course.
How Long Should You Spend in Montepulciano
It’s easy to do a day trip to Montepulciano from Florence or Rome, or elsewhere in Tuscany.
But, if you have time try to spend at least 2 to 3 nights in Montepulciano. The experience of staying in or near this walled city is really special.
If you plan on doing any Montepulciano tours, try to spend even longer in town if you are able to, so you are able to try some of the amazing local restaurants and Montepulciano wineries at your leisure too.
Skye sits on the morning sun on the steps of the Duomo in Piazza Grande, Montepulciano. | © Skye Gilkeson
Where to Stay in Montepulciano
There is a mix of hotels in Montepulciano as well as bed and breakfasts and beautiful agriturismo accommodations in the nearby countryside.
Booking Montepulciano accommodation as soon as you know you are going to visit is really important, particularly if you want to stay in the town center.
There are limited options and they book up quickly in peak seasons.
Montepulciano B&B Accommodation
This wasn’t our first visit, yet the first time we were staying inside the fortified walls to get more of a feel for the town, beyond our typical lunchtime stopover.
Having driven the two and a half hours from Rome to Montepulciano, we were looking forward to settling in, unpacking our bags, and starting to slowly climb the streets of this Tuscan jewel.
It was the early afternoon when we pulled through Porta delle Farine, one of the two gateways to the town. Pulling up outside B&B L’Agnolo Di Caroti Cinzia.
Owner Michael tapped lightly on my window, insisting he escorts our daughter and I to our room while the hubby parked the car and carried the bags up the hill.
This family-run BnB is an absolute gem in Montepulciano. While we would usually hunt down a luxury 5-star hotel, we really had our hearts set on staying inside the town walls, so we opted for a BnB instead and we had the most wonderful stay.
Nothing was too much trouble for Michael and his family.
The suite we had was very large and comfortable. The only thing lacking was air conditioning, so if you are staying in high summer you may want to request fans when booking your stay.
Il Tosco Montepulciano offers similar boutique accommodations. While it has just four rooms, for those travelling to Montepulciano with kids or other friends, you can choose to book the entire house for up to 8 guests and experience living like a true local.
Montepulciano Hotels
For those happy to stay slightly out of town there is a range of options, including luxury hotels.
Click to search Montepulciano hotels.
What to Do in Montepulciano
When it comes to things to do in Montepulciano and what to see, there is plenty of history both inside the town walls and in the surrounding Tuscan hilltop towns.
Start your stay by exploring Montepulciano itself, but make sure you schedule enough time for a few day trips from Montepulciano too. This Montepulciano travel guide should help you plan your stay, whether you are visiting for a day or a week.
Start in the Piazza Grande
Piazza Grande is the perfect place to start exploring Montepulciano.
Located at the top of the town, the expansive main square features the Duomo di Montepulciano, dating back to 1570 with its rough unfinished facade, the 14th century Palazzo Comunale or town hall offering panoramic views from its clock tower, the Palazzo Contucci, and the 16th century well, Il Pozzo dei Grifi e dei Leoni which, as the name suggests features the Medici coat of arms (as a nod to Florence), supported by lions and the griffin, representing Montepulciano.
From the square, weave your way down through the Corso, zig-zagging around the bends, stopping in at cafes, and bars, and admiring the many churches and Renaissance palaces tucked away among the narrow streets.
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The clock tower from the Montepulciano town hall offers visitors views over the town and valley. | © Skye Gilkeson
Visit the Churches of Montepulciano
Whether you are religious or not Montepulciano’s churches are worth visiting or even simply admiring their facades for the architecture and history from the street as you wander the cobblestones.
Montepulciano Cathedral is an obvious choice if you are short on time and passing through Piazza Grande. Saint Lucy is located in the backstreets (Piazza di Santa Lucia) if you are zig-zagging your way down the hill.
You will probably also pass the beautiful facade and busy steps of Saint Agostino as you head toward the town’s lower gate.
The dome of the Tempio di San Biagio enveloped in greenery is visible when enjoying the sunset over the valley from just outside of Montepulciano and enjoying the view down to the valley below from the town walls.
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Skye outside Saint Agostino Catholic Church in Montepulciano. | © Skye Gilkeson
Wine Tasting in Montepulciano
When you ask anyone what to do in Montepulciano, wine tasting will be top of the list. Wine tasting in Montepulciano is a must during your visit; whether you are simply stopping in for lunch or staying for longer.
What is Montepulciano known for? As well as its stunning architecture and fascinating history, Montepulciano is known for its Sangiovese-based Vino Nobile.
Montepulciano cellars are dotted around town offering tastings of the best wineries in Montepulciano and the surrounding vineyards.
Make sure you do one of the full wine cellar tours so you learn about the history of the wines and the towns. It’s such a wonderful experience.
There are also lots of amazing little Montepulciano restaurants and wine bars where you can stop in for a tasting with very knowledgeable waiters pouring up Nobile, the Montepulciano d’Abruzzo, and other less expensive, but also delicious drops by the glass or the bottle.
Depending on where in the world you live you will also be able to easily send some bottles of your favourite wines home to family, friends, or your own private cellar.
If you are looking for a full-day wine tasting experience here are some tips for choosing the best Tuscany wine tour.
Visit the Montepulciano Fortress
Another unusual place to go wine tasting and enjoy the view of the valley is the fortress. Located near the Porta al Prato at the top of the town is the Montepulciano Fortress.
Originally built back in 1261, the building has been destroyed and rebuilt over the centuries.
Now, the fortress is a pop-up space for exhibitions and also the Enoliteca Consortile, showcasing and offering tastings of the Vino Nobile. There is a glass floor in the wine bar so visitors can view the Etruscan ruins underfoot.
Purchase a tasting card (which you can simply top-up) and use it to grab yourself a glass or a tasting pour of wine and take it to the terrace outside to take in the views across the valley below to the Temple of San Biagio and of the Val di Chiana and Val d’Orcia.
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Skye hit the streets of Montepulciano in the early hours to capture its beauty without the crowds. | © Skye Gilkeson
Give Your Camera a Workout
The ancient village of Montepulciano clings to a limestone ridge at about 600 meters above sea level which of course means the views are breathtaking across the surrounding Val d’Orcia and Val di Chiana.
The clock tower (with views stretching to Siena), the Montepulciano Fortress, and any of the main walls at the top of the town provide a stunning panorama and the perfect location to use your camera to capture the sweeping valley surrounds.
But I also highly recommend you set your alarm nice and early one morning and wander the backstreets with your camera in hand to snap some shots of the incredible architecture and characteristic details.
If you are hoping to take some portraits of the locals, you may have to wait a little later; the only local we saw on our morning photoshoot was a slightly sleepy cat on a stoop.
Tour the Montepulciano Wine Caves
Taste-testing and learning the history of the best wine in Montepulciano, Vino Nobile are the top things to do in Montepulciano.
While the Montepulciano wineries have vines covering the surrounding hills, some also process their wines in ancient centuries-old caves, dating back to the Etruscan era below the town itself.
We booked in for a walking tour of the Historical Cellars and we absolutely loved it. A mix of history, sightseeing, wine, and food tasting, the tour was thorough and lots of fun (and one of the few we could take with a toddler in tow).
The tour runs for 2.5 hours, starting at the top of the town at Piazza Grande and working our way down the hill to finish at Cantina Ercolani.
We simply booked in the night before at the Valdichiana Living desk located in the tourist office at the Palazzo dei Nobili for 29 euros per adult. However, I recommend pre-booking your tour in the high season.
They have a range of tours from truffle hunting to cooking courses and other gourmet options to sightseeing and wellness offerings too.
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The steep Montepulciano streets welcome challenge competitors in the famed annual Bravio delle Botti. | © Skye Gilkeson
Join in a Local Celebration
If you are visiting in summer, book in early for a ticket to one of the Cantiere dell’Arte events, a festival that runs from late July through to early August.
On the last Sunday in August, the famous Montepulciano barrel race is held; the Bravio delle Botti. Pairs representing eight districts compete by pushing 80-kilo barrels up the steep slopes of Montepulciano to the Piazza Grande.
At Christmas time, the Castello di Babbo Natale Montepulciano (Santa’s Castle) is one of the best things to do in Tuscany. Pre-purchase your tickets and bring the kids to meet Santa, do Christmas activities, and see the town afterward.
There is also the Mercatini Natale Montepulciano on at the same time which is widely considered one of the best Christmas markets in Italy.
Relax at the Montepulciano Thermal Baths
About 10 minutes away from the town center is the Montepulciano thermal baths.
Said to have healing properties the thermal water is the ideal half-day destination for those needing to relax and unwind after days spent climbing the Montepulciano inclines.
Visitors can book spa treatments, work out in the fitness area or simply swim in the sulfurous waters.
Explore Beyond Montepulciano
While there are so many things to do in Montepulciano, there is a lot on offer in the surrounding villages.
It is also so close to other iconic travel destinations, easily accessible by car or train.
Florence is just a 1.5-hour drive from Montepulciano and is a bucket-list destination in Italy.
Peruse the galleries, walk the cobblestone streets, visit the incredible Duomo, and so much more. Here is our guide for what to do in Florence in 2 days.
Further north is the walled city of Lucca on the banks of the river Serchio. A lesser-known Tuscany town that can’t be missed, read our guide for what to do in Lucca Italy.
Just 2.5 hours drive north is Bologna, a city that will dazzle your tastebuds. Read what to do in Bologna.
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The views over the surrounding vineyards from Montepulciano, Italy. | © Skye Gilkeson
Skye is the founder and editor-in-chief of The Fit Traveller.
She is a journalist, writer, photographer, intrepid traveller and a former personal trainer with a passion for helping others reach optimal health.
As a TV journalist and producer, Skye has worked for household names such as 60 Minutes, Sunrise, TODAY and Nine News. She has also written for Women’s Health, Fodor’s Travel and Yahoo7 Travel, among many others.
Equally comfortable in a 5-star resort or hiking a far-off mountain, Skye loves the unexpected and enriching life experiences that each trip brings and can often be found in a backstreet chatting to locals with her camera in hand.
Skye is based in Sydney, working to master the balance between motherhood and her appetite for adventure.
Read more about Skye’s story here.