Monticchiello Tuscany is an art and crafts hill town in the stunning South Tuscan countryside near Pienza and other more famous hill-towns. Yet, Monticchiello is a quiet gem, not yet on the radar of many tourists.
It has some fascinating history, views to rival the best of them and it is an exceptionally pretty and neat town.
Perhaps even more interesting is their longstanding association with arts and crafts. Even today, you’ll find most shops are artisan craft shops selling high quality goods. Halfway up the town is a church that holds beautiful frescos. If you keep climbing through the town there is a garden (almost secret) that displays art work among the olive trees! Here, you can sit and look down at the remaining town walls and the surrounding countryside.
So, you see Monticchiello Tuscany is a town for those of you who want some peace and calm, where you can contemplate this unique Tuscan culture. Get there before everyone else catches on!
We had been driving through some quintessential Tuscan countryside, with the roofs down feeling exhilarated by the beauty of the landscape. We had driven from our rented Villa Montepulciano a relatively short drive away, but were all feeling parched (to say the least) by the time we reached Monticchiello, as Tuscan roads are often very dusty!
Luckily before entering the main, and only, gate of the town you can find a café selling refreshments. Even better is that round the back, in their shaded garden, they sell small batches of homemade gelato.
It is really, really good!! Just what we needed before exploring another hill-top town and it’s steep streets.
Actually as towns in this area goes, the streets aren’t particularly steep, so more suitable for slightly older and younger family folk.
The entrance to the village is from Porta Sant’Agata, a gothic gate, with a pointed arch and two defending towers on the side, which still display the emblem of Siena (clearer on the first picture).
Montichiello today is still almost entirely surrounded by the remains of the town walls. Sadly the towers are mostly cut off.
When you first enter the town gate, look to the left where there are some steps. You could climb these to get a view from the town wall.
There is a table setting from the restaurant below. Can you imagine a sunset meal here?
The history of Monticchiello Tuscany in bullet points
- It has Roman origins, but its history is more knitted into the Middle Ages.
- In an act dated 1156 a local count donates it to Pope Adrian IV, who made use of the castle.
- Around 1175 the town is put under the political influence of the City of Siena. Later, followed by a peace agreement between Siena and Florence, taxes were implemented to the inhabitants of Monticchiello to finance the debt of Siena.
- Monticchiello swore an alliance with the mayor of Siena against Montepulciano committing to give no shelter ‘to woman and child of the enemies, especially the wives and children’.
- Monticchiello was engaged in regular warring with Montepulciano throughout the 13th century over border disputes, until Siena intervened to make peace. So, began the construction of the gate, the Church and the remaking of the walls.
- In relative peace, from 1250 the town increased its reputation in trades and handicrafts and experienced a time of flourishing.
- The decline of Monticchiello
- begins with the Franco-Spanish war in mid-1500.
- The Monticchiellesi were forced to face the enemy, throwing stones. Although, their effort was given an honourable recognition.
- With the domination of Florence throughout Tuscany (under the Medici family) the importance of this part of Tuscany gradually declined.
- When the Republic of Siena fell in 1559, Monticchiello was placed under the Medici powers and gradually lost its importance.
- It was ceded to the city of Pienza in 1778 by the Grand Duke Pietro Leopoldo. When the Grand Duke, who was uninterested in these places in the countryside, decreed the abolition of the Council of Monticchiello, within the civil and administrative reforms of the Tuscany State.
- History dramatically returns here in 1944 with the partisan efforts for liberation.
- The Prefect of Siena sent a large group of men to tackle the Partigiani camped in the countryside around Monticchiello.
- The fighting had the fascists retreating.
- The next day German soldiers forced into the homes of Monticchiello and scared locals crowded outside the main gate. A massacre was avoided thanks to Irma Anghebeni, German wife of a landowner of Monticchiello, helped by the local priest.
Today peaceful, neat flower filled streets are full of quality, artisan craft shops.
Monticchiello is tidy and inviting, with stone houses and streets, flower boxes and very few tourists. The locals are obviously proud of their little town and flowers adorn every household.
The urban structure is unusually spacious for a Tuscan hill town, without the usual dusty, narrow alleys, and there are plenty of squares paved with stone. The inhabitants look after the appearance of their town and there wasn’t a scrap of litter to be found.
I’m fascinated by the people of this picture perfect Tuscan town. It appears as if they do everything exceptionally well. The shops are filled with quality products made by the owners, the gelato was exceptional, the houses are all kept pristine…
Not only that, these creative folk host the “teatro povero” (the peasant theatre), where the residents write and produce an annual show based on the life and history of its people in the village. It is held during the summer months (mid July to mid August), nightly in The Piazza del Teatro. This town tradition is another way it expresses it’s heritage as creative people.
Another expression of creativity is found at the small market, held beneath the trees in one of the small squares. It sells more handmade goods, including jams and leather bags.
Beneath the embroidered cloth stall a local dog escapes the heat, and seems happy to watch folk stroll about.
However, his local little pug was typically rambunctious!
This simple well is in the market square.
Everything here seems to take place at a slower pace.
I read there are little over 200 inhabitants to this town. The residential area is easy to find and is peaceful and pretty.
Pretty blooms cover the walls.
As you reach the church the residences look Gothic. Little has changes, except for tv aerials and flower boxes.
The tiny square in front of the church steps is shadowed by the thirteenth century Church of Santi Leonardo and Cristoforo.
The Church of Santi Leonardo and Cristoforo has a structure of a ‘single nave and three apses, with the Gothic facade adorned with a highly splayed ogival portal surmounted by a rosette‘.
Inside has been transformed in the eighteenth century. But there are frescoes of the fifteenth century. Because the town is off the tourist radar, you can pause and be peaceful here.
The most unexpected thing we found in Monticchiello Tuscany is a public garden at the top of the town. It is filled with pieces of art on display nestled in between old olive trees.
There are benches dotted about. Some with views out over the rooftops of Monticchiello and the stunning slopes of Southern Tuscany.
You can also see the remains of the walls and towers of the old castle.
So, if you plan to visit Tuscany soon, make sure you make time for this characterful town and it’s arty folk.
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