Montepulciano and Il Sasso

A week in Montepulciano and Il Sasso Italian School

Montepulciano is an excellent hill top town for eating and drinking well, with a bit of learning Italian at the Il Sasso school on the side.

After letting my Italian slide during the (pandemic induced) travel break, it was time to jump back on the proverbial horse. What better way to revive all the Italian that was buried somewhere deep inside my head, than to attend an Italian school.

Anyone who’s had the same idea, knows it can be tough to find recent and detailed reviews of potential schools. This is one of the reasons why I started this site (click here for past blog posts on the subject).

Previous trips included two separate visits to the Lucca Italian school in Tuscany and the Todi Italian school in Umbria. Although they were both great experiences, I wanted to try somewhere new.

During my many late nights trolling the internet, Il Sasso School in Montepulciano kept popping up. While the reviews were all very glowing, I wasn’t sure if the small town would be enough to entertain me for full week. Memories from two previous short trips included the long, steep main ‘street’ that winds its way up to Piazza Grande and the Vino Nobile di Montepulicano.

Thinking I could do worse than spend a week in Tuscany, I booked a week in October. A week in Tuscany, meeting new people, learning Italian and drinking red wines? Andiamo!

Post Highlights

  • Why Montepulciano is a good place to learn Italian
  • Overview of Il Sasso
  • School activities
  • Other activities in Montepulciano
  • Where to eat
  • Where to stay

Why Montepulciano is a good choice for learning Italian

I had a few criteria, which Montepulciano met them all:

  • It has a well-reviewed Italian school
  • There are plenty of activities in my downtime outside of school hours
  • For a reasonably small town, it has plenty of restaurants
  • It’s serviced by a bus from a main train line making it reachable without a car (though not without a bit of hassle)
  • There are plenty of accommodation options

Having now spent a glorious week in the Tuscan sunshine in an abnormally hot October, I can confirm it was an excellent choice. This statement comes with a serious disclaimer. Doing this brings a serious risk of being inspired to quit your job, buy a house in Tuscany and become a wine-drinking Italian speaking hermit …

Overview of Il Sasso Italian School

Il Sasso is a small school located near the bottom of Montepulciano’s wall old town. And by small, there were 20 students during the week I was there.

In terms of the ‘school’ day, class started at 9am and ended around 1pm with a break in the middle. Our lessons were split between two teachers, with a changeover at the break. There were 5 or so different groups and our advanced class was the largest with 10 people. I’d suggest this is the upper limit for a language class, but they made it work. Overall I found the teachers experienced, using insightful ways to teach complicated topics. Having two teachers with different teaching styles also helped mix up the day.

The week wasn’t perfect though. While the teachers are good at bringing the material to life, the lessons are mostly based on a textbook that they work through each week. For people attending multiple weeks it would be a decent way to keep the content fresh. However, on the week I attended the topic for that chapter was Immigration and Migration. Not exactly the kind of light hearted topic you want to discuss when on a holiday!

At other schools, content focused on the many aspects of Italian life – food, travelling, music, film. Topics far from semi-heavy immigration debates! By the end of the third day we asked if we could mix things up. To the teachers’ credit, they had no issues with the change – I think they thought it was heavy too!

Overall as my re-introduction to Italian learning, it was an excellent week. The only real improvement would have been a smaller class size but I just got unlucky that week.

Other activities at Il Sasso Italian School

Outside of class, the school offers daily activities with minimum numbers of attendees for them to go ahead. On the third day, about 10 of us walked from the school to the neighbouring hill town of Monticchiello. The walk took about two hours, passed through the neighbouring countryside and ended with an aperitivo. Afterwards (almost more importantly), the drive back to Montepulciano was part of the deal.

The afternoon walk to Monticchiello with Il Sasso
The afternoon walk to Monticchiello with Il Sasso

They mix up the activities each week and require minimum numbers to go ahead. Other activities range from a tour of Montepulicano, afternoon trips to local wineries or farms and cooking classes. The week I attended, only the walk to Monticchiello had enough attendees. Interest in activities varies each week depending on what the students want to do.

Non-school things to do in Montepulciano

After school finished for the day, there was plenty to keep us entertained. Highlights, besides the walk to Monticchiello, included:

  • An afternoon in Pienza: From Montepulciano, Pienza is a short 15 minute bus ride, making it an easy day trip without a car. we left at the same time as all the kids in Montepulciano were leaving school so the bus station was a bit chaotic as we were leaving! The return bus ride was much more mellow, and was easy to find to return. In Pienza we ate lunch at Trattoria Latte di Luna and had an ice cream at Buongusto Gelateria. We also spent time strolling the narrow streets and the pathway along the wall with typical epic tuscan countryside views. We also browsed the tourist shots and people watched in Piazza Pio II.
Photos from an afternoon in Pienza
Photos from an afternoon in Pienza
  • Evenings people watching in Piazza Grande: There’s just something about this piazza that feels familar. With its mini-castle-like town municipal building and the unfinished cathedral that gives off “we ran out of money” vibes. Then of course the very jolly people walking out of a Contucci Cantine wine tasting. Combined with watching the sunset from the town walls behind the tower and then taking a seat on the rock bench from the Contunicci building, it just feels like Italy. *starts looking for flights*
  • Afternoon drinks and a cheese plate at E Lucevan le Stelle – Wine Bar Bistro: Since it wasn’t a meal, I’ve listed ‘drinking’ as an activity. The bistro has a lovely outdoor deck, with, you guessed it, tuscan hill views. It sits near a popular viewing spot so besides the wine and cheese, and despite it being located “out of the way”, there’s some decent people watching. I still remember how that first glass of sparkling rose went down on an unusually hot October afternoon.
  • Wine tastings at Cantina Crociani, Cantina Contucci and Pulcino Di Matassini Ercolani Gabriella Fattoria: I’ve decided to add in the wine tastings as a group, though the experiences were very different. The best experience was at Cantina Crociani. It’s small, the man running the tasting was lovely, and we didn’t feel rushed and expected to buy anything. And there was a cat. It’s located away from the main ‘drag’ so doesn’t get overwhelmed with visitors like the other two. The was my favourite.
  • Catina Contucci is next to Piazza Grande and is one of of the more popular spots. I’m sure the staff are exhausted by closing time and we visited, at the end of a long day. I’m guessing the lack of enthusiasm reflected our poor choice of timing. I didn’t care for any of the wines but since the tasting fee was waived with purchase, we bought a bottle. Definitely not my favourite.
  • And finally Pulcino Di Matassini Ercolani. I’m torn to say anything bad because the experience walking through the old storage areas, seeing the old equipment and the experience of being in the old cellars is pretty cool. But the wine tasting though was not enjoyable. I get a sense their top priority is to cater to tourist groups who will spend big. We were happy to buy wine but the experience was so unenjoyable we didn’t buy a single bottle. Again it might have been a timing thing, or we were unlucky with the server but, dang, not good!

You won’t go hungry – restaurants in Montepulciano

Despite our apartment accommodation, the restaurant options in Montepulciano reminded me that visiting Italy is not the time to try out new recipe ideas. Let the people who love to cook, do the cooking!

  • Gattavecchi Winery: We ate here for a late afternoon lunch and it was one of the best meals of the trip. As a winery, they offer a wine tasting options so you get to try three glasses of wine. We then also ordered meals to go along side it. Our server was very entertaining, there was Italian music playing, the weather was perfect and its located near the edge of town has lovely views. The group of ladies on a wine tour at the cellar door seemed to be having an even better time than us (and that’s saying something). Would highly recommend this one.
  • Porta di Bacco: When I said Gattavecchi was a favourite, it was great, but Porta di Bacco was amazing. It’s a bit misleading to compare them as Porta di Bacco is an Osteria and operates at a different (price) level. This was my favourite meal of the trip. Not just the service, the food or the setting but the combination of all three. Even the locals mentioned it was the one place they tell visitors to try (if they can get in). On that, make sure to reserve a table, a couple of days in advance.
Dishes during our lovely meal at Porto di Bacco
  • Lieviti Pizzeria: As the name would suggest, they specialise in pizzas. You walk past the kitchen (and the pizza ovens) as you enter the restaurant and the smell of everything pizza traps you and won’t let you leave. The dining area has a few different ‘nooks’ and has an overall great atmosphere. Would recommend for the pizza and the “cave-like” dining area.
  • Osteria Del Conte: At the top of town, this was another Montepulciano gem. As I’m writing this, I’m starting to wonder if there are any ‘bad’ places to eat in this town? The dining area outside is pretty and we had a lovely meal. Our reservation was for 6:30pm and we were the first to arrive.

Where we stayed

Montepulicano has a lot of accommodation options for various budgets. Depending on what you’re after, you can stay at a hotel, B&B, self-catered apartment or even a homestay organised through the school. I usually book with and search by area and price.

But having not travelled for a couple of years, I splurged and booked an apartment with a lovely terrace over looking the countryside. I booked through the owners directly, which is something I try to do when I can. THe host, Nico, was fantasic and the apartment was a beautiful place to relax.

Link to the Sant’Antonio website – click here

Closing thoughts

After spending a week in Montepulicano learning Italian at Il Sasso, I could have easily spent another week (or three). But variety being the spice of life, we continued north to Verona and Venice for the second half of the trip. On another holiday, I can easily see myself visiting again, but maybe with a car next time.

Have you visited Montepulciano? What were your favourite things to do and restaurants? Let me know what we missed!

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