Montepulciano: More Than Just Wine
By Gillian Boyd Published 14 August 2026
Montepulciano is so much more than its wine. A medieval hilltop village with an underground history, art, towers and stunning views.
Having appreciated Montepulciano wine for many years, we just had to stay there when we got to Tuscany. In my head it was vineyards and I hadn’t considered there would be a medieval village and so much history linking it to the other towns and cities. But this is one reason to travel – to learn.
We stayed in an apartment on the edge of the town with parking included.
Montepulciano and surrounding countryside in Tuscany
Montepulciano Tower in Tuscany
Medieval Hilltop Villages – What to Expect
Exploring medieval villages in Tuscany all follow a similar pattern.
Park outside the village walls. Walk uphill and enter through a huge stone City Gate to find the historic village. It will be full of independent specialist shops and restaurants selling high quality produce.
Continue walking the winding narrow streets, admiring the architecture, the stone work or palate of pale burnt siena paintwork. Zigzag your way to the highest point of the hill.
Here you will find the most important buildings – usually a tower, Cathedral or church and the main square. It will be beautiful, probably have a welcoming breeze and stunning views across the valley. See also Siena for information on San Gimignano, Castello di Brolio and Fonterutoli.
Explore Montepulciano and climb the tower
We walked up the hill, through the town to the Piazze Grande and climbed the Tower. It wasn’t very high but the views were great.
Through the Archives Office
After buying tickets for €5 each, to my surprise the signs directed us through the archives office full of shelves and shelves of land registry box files, to reach the staircase for the tower. I took a sneaky peek at the titles on the spines and some dated back hundreds of years.
The staircase and ladder up was very narrow, with not much headroom, if you are claustrophobic, I would skip this.
A Man and 2 Bells
At the top there were 2 bells and a man, although you couldn’t see either from the ground.
We spent quite a long time up there enjoying the extensive views, the pleasant breeze and chatting to the man. I exaggerate – we spoke very little of each other’s language so there was a lot of gesturing but luckily, I am good at playing Charades and reading body language. He was a font of knowledge and pleased to share it. Another little highlight of our trip.
View from Montepulciano Tower, Tuscany
Guess My Job
At first I thought his job was to ensure no one rang the bell or did anything foolish at that height (maybe that’s my school background coming through). He had a more important job – as a fire lookout. In France, this job is often done by students in the summer months.
Between 10am and 6pm (when the tower is open), he patrolled the top of the tower looking for signs of fire in the surrounding area. He used a walkie talkie for communication with the other watchmen, in the neighbouring districts, some 30 km away. I did say the views were extensive.
Watchman
It was all too easy to imagine how a fire could break out and spread rapidly. Part of me was reassured that someone was looking out for our safety and that of the land, while part of me thought of how common it has been for wild fires to have ravaged the land throughout the world in recent years.
Perhaps his job will become more common again in the future. A case of history repeating itself as watchmen have existed since Ancient Roman times and throughout Medieval Europe, as early warnings of fires.
Torre di Pulcinella Clock Tower in Montepulciano
Torre di Pulcinella
Visible from the ground is the mechanical statue of Pulcinella, a black and white clown from traditional Neopolitian theatre. Standing on top of the clock tower, he strikes the bell on the hour. He’s a hard worker as he has been doing it since 1680.
Underground City Wine Tour in Montepulciano
Underground City Wine Tour
When we first walked inside the city walls of Montepulciano, we had noticed some promoters for an Underground City Wine Tour. They said it was free but in our experience nothing in life is free, especially if it is due to last 45 mins.
Is It Really Free?
We were intrigued and wanted the tour but not if it meant suffering a hard sell. We were sceptical and did some research checking out online reviews before finally putting our names down for a tour later. And we were so glad we did! The tour was great and I would recommend it!
Only Us
We were the only ones who had signed up for the 5pm slot on the board outside the shop for the Underground City Wine Tour. As a consequence, we could interrupt with questions and of course we had many.
The 45-minute tour had everything we like in a tour. We learned about the history of the town and region, some folklore, the process of wine making and even saw a torture chamber as we passed through the series of underground chambers and passages.
One of the cellars of Underground City Wine Tour in Montepulciano
Designed by Leonardo Di Vinci
We started in the cellars where we saw barrels made of Croatian Oak. At the top of each barrel was a glass contraption, designed by Leonardi Di Vinci, that allows the winemaker to know the barrel is full without opening it and risk contaminating the wine. It is used everywhere, not just Italy.
Cellars
Another cellar housed oval shaped custom made 2,000L barrels so they could fit in the opening and through the narrow streets.
Some of the barrels had small openings and needed to be cleaned by hand. Our guide showed us a video of a man climbing through the small hole into the barrel and scraping it clean. It was impressive, especially when we realised, we had met him earlier when we signed up for the tour! He was tall and slim and flexible to have squeezed through such a small hole.
Secret Passages Underground
Secret passages joined underground rooms that used to belong to 5 different families in medieval times, but now they were owned by one family and had been joined into a circular route under the city of Montepulciano.
Prison & Tortue Chamber
At one time, part of this system of caverns had been a prison with the furthest away section a torture chamber. Well, who wants to hear the screams? It was all so easy to imagine the impact of the procedures, such as the metal chastity belt for women and the enema filled with ginger that was used on men.
Corner of Love in Secret Passages Under Montepulciano
Corner of Love
But the stories we heard were not all doom and gloom. Our guide told us of a love story between 2 rival families when the children met collecting water at the well. Ahhhhh, their very own Romeo and Juliet who met at ‘Il pozzo del amore’. They could see each other through the holes.
Grease the Pole
We discovered the origin of the well used phrase ‘grease the pole’. A reminder to literally grease the pole, so the horses could be released quickly, as they were at war and every minute counted.
It was also the code name of the powerful Medici family based in Florence, who had forged alliances with the family in Montepulicano, even though Siena was geographically closer.
New Restaurant
We walked through a tomb from 1000BC pre-Roman times which has been turned into a new restaurant and bar. A cool place for a private party.
It was an excellent tour and we thoroughly enjoyed it. We would have happily tipped well if it had been on a free walking tour.
By the time we had returned to the wine shop for the wine tastings we had discovered our guide was of Italian descent but grew up in Argentina, so I got to speak a little Spanish and reminisce about our trip to Argentina a year or so earlier.
Local food and wine on the Underground City Wine Tour in Montepulciano
Food & Wine Tasting
The wine tastings in the shop were accompanied by generous Tuscan delicacies such as pecorino cheese, truffle paste and crisps, sun-dried tomato paste and salami. All were available for sale in the shop.
No Hard Sell
They tasted really good so we bought some food stuffs and a bottle of wine. There was no pressure at all to buy and the bottle of wine we chose was only €2 more than in the supermarket. Obviously, it is a business but we felt the whole experience was very enjoyable and well worth what we spent and more. We had been there for an enjoyable hour and a half in all. We were very happy and recommend the tour.
Melting Clock by Salvador Dali in Palazzo Bracci Art Exhibition in Montepulciano
Visit the Art Exhibition in Palazzo Bracci
Dali: Eat Me!
Inside the city walls of Montepulciano, we stumbled across a small art exhibition. We walk past ‘The Elephants’ carrying a golden obelisk on his back despite impossibly thin legs. Not such a surprise you think, when you discover that it is the Salvador Dali exhibition, ‘Eat Me!’
In the first room upstairs, I melt at the sight of ‘The Melting Clock’.
First of Many
This was the first exhibition from the Beniamino Levi collection and others are promised each year. It includes artworks from Dali, Picasso, Chagall and other great masters of the 20th century all tastefully displayed in the intimate setting of the frescoed walls of the Palazzo Bracci. See lartuniverse.com
Even the view from the balcony was stunning. It felt more like I was in an art collectors’ home rather than an art gallery.
Dali is one of our favourite artists, so we were in heaven. While limited edition prints were available for sale, they were beyond our budget. Ironically, there was more sales pitch here than at the wine tour.
Free Natural Spring Water Dispenser in Montepulciano
Drink Natural Sparkling Spring Water
Just outside the main city gate to Montepulciano is a vending machine that dispenses natural spring water and naturally sparkling spring water for free. Yes, for free! This was surprising to us, as so many other countries charge for water.
We filled our water bottles each time we passed and it tasted good. Lots of places in Tuscany offer natural water from springs for free, including in the Piazza di Campo in Siena.
View from Pienza, Tuscany
Places to Visit Near Montepulciano
Whilst we were based in Montepulciano, we visited these places using our hire car. However they are still easily accessible if you are based in other parts of Tuscany. For example Pienza is just over an hour’s drive Siena.
1. Pienza
On our 20 minute drive from Montepulciano to Pienza, we passed golden fields lined with dark Tuscan cyress trees. Pienza is a pretty fortress town in the Val d’Orci where we spent 2 hours exploring. A group of cyclists rested in the shade as we walked around the old city walls with super views over the valley.
Ideal Renaissance City
Full of narrow streets with many colourful flowers in pots, the town was the birthplace of Enea Silvio Piccolomini who later became Pope Pious II. He transformed it into his ideal of a Utopian city and so Pienza is often known as the ‘ideal Renaissance city.’
The Papal Palace, the Palazzo Piccolomini has a large loggia with hanging garden and views across the Val d’Orcia. Entrance is €12.
Although this is considered the highlight of the town, we just weren’t feeling it that day so didn’t visit the gardens. We had already seen the view from the city walls.
Clock Tower and Streets in Pienza
Organist Playing in Pienza Cathedral
Organist Playing
Instead, we were drawn by the music from the Duomo. It was the Pienza International Music Festival. We entered the light and airy Duomo in front of the Palazzo Piccolomini to hear the organist perform.
While in the atmospheric Chiesa de San Francesco, we listened to a woman play a beautifully painted harpsichord.
Home of Pecorino Cheese
Pienza is also the home of pecorino cheese so we bought some after trying a couple of different types which the lady vacuum sealed for our journey home. A nice way to extend the holiday feeling when you get home.
Red flags of Montalcino, Tuscany
2. Montalcino
We parked for 3 hours at the edge of the hill top town of Montalcino, as we intended to stop for lunch.
Larger than Pienza, it was not too busy with tourists, though the tour groups began to arrive late afternoon. The atmosphere was still festive with the town decorated in many red flags and I thought the fortress looked like a great place for a concert.
After lunch we went for a wine tasting at aptly named Grotta del Brunella as we wished to try the Brunella wine, as it is different to Chianti. Yes, we do like a wine tasting.
Walls of Monticchiello, Tuscany
3. Monticchiello
To reach the medieval village of Monticchiello dating back to the 1200’s, we drove along gravel roads avoiding horses, people and cyclists enjoying beautiful rural Tuscany. We had hired a small SUV so we were comfortable we could negotiate any road.
We walked the shaded path along the outside edge of Monticchiello, with great views out across the valley towards Pienza.
Art Trail
Alone, we continued through an olive grove, displaying paintings on rusty easels, as we listened to the cicadias singing loudly. It was a surreal moment.
Public Laundry
Further on, we headed past an old public laundry with its multiple stone sinks next to each other and I thought about how the women probably gossiped and chatted as they worked here. Now that social role has gone but it has been replaced by a basketball hoop for a different social group.
The place was empty. We wondered where everybody was. A little further on we heard mass being performed – we had forgotten it was Sunday.
Storm Coming
As we drove along SP88 with stunning views of golden fields on both sides of the road, dark clouds loomed overhead for a storm that was brewing. Thunder and lightning serenaded us later that night. We sat on the deck chairs of our patio and watched the lightning in the distance.
For information on San Gimignano, Castello di Brolio and Fonterutoli see Siena.
Final Thoughts
For me, the best thing about exploring Tuscany was all the little surprises. And there were many. Mostly of my own ignorance.
If I had thought about it, I should have twigged why the paint colour burnt sienna is so called – because it is literally the earth of Siena burnt to produce the reddish brown paint and it remains yellowish brown in its raw state. The very colour palate of the whole of Tuscany. While Umber, with its warm tones of brown and olive is the next colour on the wheel and originates from the state of Umbria, which borders Tuscany.
But somehow I didn’t expect the fields to be golden, the views to be so expansive, the art trails, the music festival and the people we met. Everything was just more. Everything was done with passion – to the best that you can manage. Each thing appreciated in its own right. It may have taken me 60 years to get there but I had a lightbulb moment when I joined the dots.