Montepulciano – My Favourite Tuscan Town

I love Montepulciano and I love saying Montepulciano.

This medieval walled city is my favourite Tuscan town. After reading Under the Tuscan Sun many years ago I really wanted to visit Cortona, Tuscany. When I travelled through Italy with my daughters, we visited Cortona and enjoyed a wine tasting in Montepulciano while we were there. Since then, it’s always been Montepulciano for me.

Montepulciano was an unexpected delight that I treated myself to for nine nights. My previous stay in Scansano hadn’t gone to plan, so I looked at the map, noticed Montepulciano was only about 100 kilometres away. And that’s where the Fiat headed.

I had written in my travel journal that it was just over a two-hour drive after taking the wrong roundabout exit a couple of times. I remember the drive and stopping to look at the Tuscan view which was breathtaking. Driving up the mountain to reach the town was quite slow as I was following a tractor on the two-way road. I really didn’t mind as it was much easier to enjoy the view going slowly.

Finally reaching this renaissance hill town, I was following directions to my accommodation which had parking included.  I drove down a narrow street past people’s homes until I came to a vacant allotment used for parking. The accommodation manager kindly came to collect me and my suitcase from the car park. The main street runs from the gates of the town up a long, steep, winding hill, with wine bars, shops and restaurants scattered along the way.

After checking in to my accommodation, which was a not too shabby attic room, I spent the rest of the day eating, drinking and walking my way around town. Dinner was at a popular restaurant with a few levels which overlooked Tuscany, with twinkling lights in the distance.

By day two, I already knew I didn’t want to leave. Originally, I had planned to visit neighbouring towns. However, during the middle of the day it was extremely hot and a high temperature warning was issued for this area, so I decided against it.  Like everyone else, I retreated to my attic room until it became cooler later in the afternoon. A ritual I continued throughout my stay.

When it had cooled down, a wine tour had my name on it. The tour led me down many stairs below street level through the ancient Etruscan tunnels where the wine cellars are kept. After a short time, we arrived back at the wine shop for the wine tasting. Several wines were available for tasting while listening to a short talk about the wine region. Our Italian host also gave us the advice “Don’t trust Italian men”.

It was still quite warm after the wine tasting, so I decided to jump on a fun, little red hop-on hop-off  train for the last tour of the day. It was a great way to see parts of the town I would have missed otherwise.

Breakfast in Tuscany

After two nights, I was feeling comfortable here. I was just one of many tourists roaming the streets.

There are many beautiful restaurants along the main street and I decided to have breakfast at the Art Nouveau “Café Poliziano”.  Sitting on a sunny terrace overlooking Tuscany, I had a cappuccino and my first pistachio croissant — it definitely wasn’t my last.

Dragging myself away from this idyllic setting, I wandered through town. It wasn’t too busy yet and the buildings were providing shade on the streets. It’s easy to lose yourself for a few hours among shops selling hand-painted Italian ceramics and jewellery, art galleries and several gelato shops spread along the main street.

At the top of the main street is Piazza Grande, surrounded by imposing historic buildings, including the Cathedral of Santa Maria Assunta. For all the Twilight fans, the piazza and cathedral were used for filming The Twilight Saga: New Moon, with a temporary fountain built in the square for the film. I would sit there in the late afternoon, enjoying a cold Peroni while imagining the movie being made where I was sitting.

There are little alleyways that also lead down to the wall of the town from where you have beautiful views of the Tuscan hills. My favourite sighting for the day was a gorgeous ginger cat sitting behind black iron bars at a street-level window, happily watching everyone pass by.

I wasn’t able to extend my stay at my accommodation, but the manager told me his friend had recently finished renovating some apartments that were really nice. Within minutes of him calling her, she arrived to show me the apartments.  Only a few steps down from where I was staying, we entered through huge wooden doors and headed up the large but worn marble stairs to the top floor.  There were four beautifully decorated apartments which had never been rented. I had my pick.

I chose the one overlooking the main street because it was always lively. Antique furniture filled the modern apartment. The owner was very proud of the wooden floor, which she told me was “real”. The building was originally a palace and there were frescoes on the ceilings and walls in the foyer adjoining the apartments.

A Festival Below My Window

From my window, I could see the 400-year-old masked figure “Pulcinella”, who struck the bell every hour on the clock tower.

One afternoon, while enjoying the air conditioning in my room, I heard a loud banging sound. I opened the shutters and, to my amazement, there was a drumming band directly below my window. The band was following a line of flag twirlers making their way up the main street.

It was the start of “Calici di Stelle”, a nationwide Italian wine celebration held under the night sky. There were wine stations positioned around the town, including one on the steps of Chiesa di Sant’Agostino which I could see from my window.

Later that night, I joined the crowds that had gathered in Montepulciano for the festival. The steps of the church had become a stage for a band. Further up the street, there was a larger area set up with food and wine tents under coloured lights.

For fifteen euros, you could buy a wine cup which you could hang around your neck and have it refilled at the different wine stations. I decided to buy a glass of wine at the station on the church steps and stayed to enjoy the music.

My time in Montepulciano passed quickly, and I was about to head north to Poggio, another Tuscan town approximately 240 kilometres away. Before leaving, I purchased two bottles of wine, a Chianti and a Bianco, both from the 2022 vintage.

As I was packing my car, I noticed the town was filling with crowds of people.

It was Ferragosto, Italy’s biggest summer holiday.

La dolce vita!

Thank you for reading. Follow along @roamingwithleila for more travel stories and adventures.

Travelling through Italy with me? You might enjoy reading about my time in Venice.

Planning a trip to Montepulciano?

You can find more information on the official Montepulciano tourism website.

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