A Week in Montepulciano

My only previous experience in Montepulciano was a 2-3 hour visit while on a walking tour of Tuscany.  All I remember is walking through Piazza Grande, then down the steep hill past Tempio San Biagio.  As I mentioned in my Il Sasso Language School post, I thought a week attending the school would give me the chance to visit other towns in the area like Cortona and Pienza.  But the school not only didn’t have the activities I hoped for, Montepulciano is the hill town to end hill towns and doesn’t lend itself to exploring the area.  (See Getting There below)

The Plan

When my sister decided to join me on my trip and stay until we went to Rome,  (see Six Days in Rome post), we agreed that in the mornings, while I was at school, she would do her favorite thing of going to churches and then we would do activities together in the afternoon.  The first part of the plan didn’t work out too well because my sister developed some health issues and didn’t feel comfortable walking around by herself.

The school had agreed that my sister could join in their activities but that week the activities  included a cooking class for 25 euros, what sounded like a walk in a field for 25 euros and a trip to Lake Trasimeno for 50 euros.  The first two weren’t appealing and having been to Lake Trasimeno in 2018 (see Perugia, Lake Trasimeno, Assisi and Cortona post), I didn’t want to pay 50 euros to see it again.

So we made our own activities and had an enjoyable week despite the disappointments.  In large part that was because we rented an apartment (see Where to Stay below) which was not only very pleasant but had a great location.  I’ve copied in the map the owner of the apartment gave us and assuming it follows the normal protocol of north being at the top, our apartment was in the southwest corner of the town on via del Poliziano, which connects to via dell Opio del Corso and via Voltaia nel Corso.  Those streets lead up from Piazza Erbe following the wall.  While it was a hike up to Piazza Grande and the Fortezza Medicea and down to Tempio San Biagio, they were all worth the work.  So we did lots of great walks, some just ‘fannying about’ or shopping, some going to specific sites.


Things to Do

Fannying About/Walks around Town

Montepulciano seems to have equal numbers of enoteca, churches, palazzi and shops.  The latter range from tourist shlock to fairly high end leather and clothes.  Our first afternoon, after settling into our apartment, we walked from via del Poliziano to via dell’Opio and part way down via di Voltaia looking for a grocery store and also for backpacks and sweaters.  I thought I’d found a good deal on a sweater but when I looked at it more closely I realized it was made in Bangladesh.  Nope.  The same was true of backpacks.  We saw a shop that seemed to have good prices but when we went back to check them out more closely, we saw that they weren’t particularly good quality.

Wednesday I walked to the tourist office just outside Porta Prato  Porta del Prato Montepulciano on the advice of my teacher who said I could buy train tickets there.  (The answer from the staff person was, ‘Yes but come back tomorrow.’)  As I walked from school near Piazza Erbe down via di Gracciano nel Corso through Piazza Michelangelo, I noticed some appealing shops.  So Thursday when my sister and I went back to the tourist office, we stopped at a couple and I bought a really nice red leather backpack which was a life saver when I was on my own.  We also bought sweaters from a couple of better women’s stores on via dell’Opio that same afternoon.

I wish I’d done more research before the trip on Montepulciano’s palazzi and churches.  Piazza Grande is the site not only of the Duomo with its rough brick finish, but of Palazzo Communale, the town hall with its clock tower, Palazzo Contucci, Palazzo dei Nobili and Palazzo del Capitano del Popolo.  We did walk through Piazza Grande twice, stopping for coffee on one occasion. But we always seemed to be on a mission–looking for a bank or looking for a lavanderia where we could dry our clothes and didn’t linger or explore the palazzi.  I also noticed the odd looking structure in the middle of Piazza Grande, but didn’t realize until later that it was a well or fountain, il Pozzo dei Griffoni dei Leoni.

Tuesday as we walked from Piazza Erbe through Piazza Michelangelo and outside Porta Prato  to the Conad’s supermercato, we walked past Colonna del Marzocco and Chiesa di San Bernardo, a former convent, without realizing their significance.  There is also a beautiful church (Chiesa St. Agostino) in Piazza Erbe near Il Sasso.

Chiesa St. Agostino Chiesa St. Agostino

Generally we were focused on taking pictures of the stunning views from the walls.


Italia GFNY Bike Race


I usually check my guide books or online to see what festivals or activities may be available in a town I’m visiting.  That’s how I learned about Il Carro Matto in Firenze (see Il Carro Matto post)  But I didn’t do that for Montepulciano thinking the school would be my source of activities.  I’d never heard of the Italia GFNY Bike Race but it seems to be a pretty big deal and the link above has a great video showing the bikers racing across the valley and then up the hills to Montepulciano.

GFNY Montepulciano       Basically we just stumbled on the race.  Sunday morning we walked up to Piazza Grande for a coffee.  While sitting there we noticed  some people setting up what turned out to be the finish line in the piazza for the bike race.   (And it was my sister who did some online research and figured out what the race was.)

In the afternoon, we did our usual walkabout, originally looking for a place to sit in the sun but the town was packed.  As we walked we saw lots of bikers and their entourages.  We eventually settled on Enoteca Perbacco (see below) where we could see the bikers grinding up the hill.

Tempio San Biagio


Tuesday after shopping at Conad’s which is outside the city walls, then taking the small local bus back to the apartment, we decided we couldn’t waste the rest of the day and decided to walk to Tempio San Biagio. It was drop dead gorgeous, the nicest day of our trip at that point.  Starting at our apartment we went right on via del Poliziano a few meters then right at the corner by Chiesa di Santa Maria dei Servi. I turned left too soon and got us on the wrong road, but we ‘Daniel Booned’ down a gravel road that came out at the street in front of San Biagio.  Both as we ‘Daniel Booned’ and at other times during the week, we were able to get some nice photos of San Biagio from a distance.

The ‘temple’ looked stunning against the cypress and blue, blue sky.  My sister went inside and after seeing her pictures as well as  the interior on the web site above I wish I had.  Tempio San Biagio interior Still it was wonderful walking around the grounds and looking at the views plus it was the perfect day for beautiful photos.

There is a small cafe across from San Biagio and the street back up to the centro (via San Biagio) starts there. It doesn’t look that steep near the cafe but as you can see in the pictures below it quickly becomes a strenuous uphill climb. Via San Biagio ends at the northwest corner of the city at via de Grassi. (And as we were taking a break on our climb, a guy in a truck drove by, yelling, ‘I love American women.’  LoL)

But we made it back to the apartment with no problem, took Aleve and had a panino and vino on our terrace.  


Montepulciano is the epicenter of the Vino Nobile wine making and there’s an enoteca about every 10 feet.  Some are associated with specific vineyards and offer wine tastings.  Others offer light snacks (‘tagliere’ or meat and cheese trays) and wine by the glass.

Perbacco Enoteca

Sunday afternoon as we strolled around, getting to know the town, we looked for an enoteca with a terrace where we could enjoy the bike race and the sun.  But as I said above, the town was packed.  As we walked up the steep hill that leads to Piazza Grande we noticed this little enoteca and decided to stop.  We had a nice meat and cheese platter and a couple of glasses of wine all with a great view of the bike race or more accurately the bike grind.

Enoteca Caratello

We stumbled on this cute little place our first afternoon in Montepulciano, exhausted and starving after driving from Montalcino to Siena, dropping of our rental car and then taking the train to Montepulciano.  We went back two more times during the week, each time having 2-3 glasses of wine, usually the local rosato, and a ‘tagliere’.  Our favorite tagliere was one that had crostini topped with diced zucchini in olive oil and herbs.  Yum!!

We only saw one other couple there the three times we went so please, if you’re in Montepulciano, go there.

Enoteca la Fortezza

One of my teachers at il Sasso recommended this enoteca and it is fabulous.  As its name suggests it’s part of the Fortezza Medicea which alone is worth the visit, built on the highest point in the town with stunning vistas.  There are interesting sculptures outside the fortress and unusual art inside.sculpture outside Fortezza di Medicea

So Thursday after my sister and I had done some shopping, we dropped off our goodies then headed up the hill to the Fortezza.  We took the same street that eventually leads to via San Biagio but turned right just past Piazza Santa Maria continuing up the steep hill on via di San Donato to the fort.

The enoteca itself is built over an Etruscan archeological find and has glass floors over the ruins.  It’s disconcerting at first but totally amazing. The staff gives you a card which is tied to your credit card and you simply tap the card next to the wine you want to try.  You can taste any of 100’s of local wines.  Plus you can order a tagliere to sop up the wine.  We loved it so much we went twice.

There’s a wall of glass with doors leading to a beautiful terrace that would be wonderful in warm weather. Even though it was rather cool and cloudy both Thursday and when we went back Friday afternoon, both my sister and I went out on the terrace and took lots of pictures of the views out over the valley.

Where to Eat

Trattoria di Cagnano

We walked past this little trattoria multiple times during the week.  And since I hadn’t seen many other restaurants as opposed to enotecas, I took a chance and as we walked by early Saturday afternoon, I stopped in and made a reservation for our last night in Montepulciano.

I later wrote that ‘we had a super nice dinner last night at Trattoria di Cagnano–grilled lamb chops, roasted potatoes, nice bottle of wine, decadent chocolate cake and 2 ½ hours of interesting people watching.’ Trattoria di Cagnano

In retrospect I’d call it an excellent dinner especially compared to our experience at il Grappolo Blu the week before.  Service was great and our bottle of house wine only cost 8 euros compared to a half bottle at il Grappolo that cost 30 euros.

Where to Stay

Residenza Stuart/The Nest House


This was a great choice for the week.  We were on ‘piano uno’ or the first floor which in Italy is what we in the States would consider the second floor.  Signora Stuart who owns and manages this and two other apartments in the building, met us at the door and helped us lug our heavy bags upstairs.

The ‘Nest House’ is the smallest of the apartments but it was very comfortable.  (And the pictures shown at the link above are quite accurate.) There is one large room with a sleeping area, a desk, a couch and TV, and a table and chairs.  The bathroom was a decent size and there was a large closet and chest of drawers just outside the bathroom.

The kitchen was quite small with just a cook top, small refrigerator, sink and washing machine.  We couldn’t figure out the pod coffee machine, just getting brown water.  So we bought regular ground coffee and tried using the ‘moka’ but couldn’t get it to work either.  It was a good thing you could get a great cappuccino in town for a 1,20 €.

After three weeks of traveling we loved having a washing machine and got caught up on all our laundry.

But mostly we loved using the beautiful terrace, having vino and sometimes panini on nice afternoons.

The apartment is directly across from a lookout point with spectacular views of the valley.

Signora Stewart is very pleasant although not always available.  Our only problem was that neither of us could get the key to work so we had to walk through a storage closet to the terrace and into the apartment through the terrace doors.

Getting There

I assume the less than stellar activities were due to the fact that Montepulciano is somewhat difficult to reach. I tried diligently to find a car rental company from which we could rent a car in Siena and drop it off in Montepulciano.  Nope.

So our only option was to take the train from Siena to Montepulciano.  The web site for Il Sasso advises students to get off at the Chiusi Chianciano Terme station not the Montepulciano station, saying that there aren’t taxis at the Montepulciano station.  Due to a miscommunication with my sister we got off at the Montepulciano station.  I was in full press panic but after walking up the hill behind the station, we saw a taxi stand.  So I went into a bar next to the station and asked if they would call us a taxi.  It took about 20 minutes for the driver to get there and he charged us 30 euros to drive us to our apartment.  At the time we thought it was reasonable so we hired him to take us to the Chiusi station for our train to Rome and he ripped us off for 60 euros.

The Montepulciano train station is 11 kilometers from the centro (roughly 7 miles) and the Chiusi station is 25 Km from the centro (roughly 15 miles).  The reason for the fairly long distances to the stations is that Montepulciano is one of the highest hill towns in Italy.  Chiusi is the larger station and usually you have to take the train from there to cities such as Rome or Firenze.

The bus station is somewhat closer, just outside the city walls not far from the Conad’s supermarket.  It may be a better option, depending on your starting point.   I stopped at the Tourist Office one afternoon to ask about local buses to the surrounding towns.  The information they gave me was very confusing so we didn’t attempt to take a bus to Cortona or Pienza.

But hopefully the galleries of the views show why the town is worth any inconvenience.


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