Certosa di Pontignano

7.2 Eclectic beauty

The charm of Chianti, amidst panoramas and ancient parish churches

From Pispini to Romana, Siena is seen at an angle with vegetable gardens that reach all the way to the bottom, leading down from the walls; while the high rectangle of Porta Pispini bears the large painted tabernacle above the entrance. The corner where the gardens are is recessed; while the houses are linear and the two sides are at the same height.

(Federigo Tozzi, Taccuini)


Leaving Porta Pispini, you can admire the mighty 14th-century walls leading to Porta Ovile and the imposing 16th-century fortified bastion, the work of Baldassarre Peruzzi, a Sienese military engineer and architect who left testaments to his work in Siena and other Italian cities.
Porta Ovile, the railway station, and then take the cycle path that runs parallel to Viale Giovanni Paolo II, also known as Strada Fiume, and will take you to SR 222 Chiantigiana.

After just one kilometre, at Colombaio, take the less busy SP 102 di Vagliagli on the right. The initial stretch runs downhill until you reach the bottom of the valley; the sweeping view looks out towards Chianti in a setting dominated by the cultivated countryside. Siena is only a few kilometres away, and can still be glimpsed on the horizon as you round a few bends, but the city remains ‘far away’—it’s like pedalling through an area made up of countryside and nothing else. At the end of the descent, there is a seven-kilometre uphill stretch, some of it demanding, that takes you up to Vagliagli, at 500 metres above sea level, in the middle of Chianti region. If you wish to ease the route without reaching the village, you can take the road on the right that indicates ‘Pontignano’ after a couple of kilometres of ascent. Otherwise, continue on to the small centre of the Sienese Chianti from where you can admire an extraordinary panorama of the hills of this world-famous ‘land of wine’. To enjoy an even more magnificent view, just before arriving in the heart of the village, you will need to literally climb a couple of hundred metres to the memorial stone that commemorates the heroic death of partisan Bruno Bonci. From here, you can see most of the territory of the province of Siena: to the west, the rolling profile of the Montagnola Senese; further away, the Poggio di Montieri and Cornate di Gerfalco; to the south, Mount Amiata, the Poggio di Radicofani and

Mount Cetona; to the west, the nearby Chianti hills, and further away, Pratomagno.
Vagliagli is a village that dates back to the 13th century and has a curious etymology to its name: Vagliagli appears to refer to ‘valle degli agli’ (valley of garlic), to the extent that the town’s coat of arms shows a hand clutching a bunch of wild garlic. In truth, the place name refers to ‘Vallialli’, ‘Valle di Allii’, or the ‘valley of Allius’, who was most likely the lord of the land. For centuries, the village was a castle, an outpost in defence of the city of Siena.

From Vagliagli, head back downhill for approximately five kilometres until you reach the junction on the left indicating ‘Pontignano’ and its splendid Certosa (charterhouse). It is a compound characterized by eclectic beauty, as can be read on the official website of Ambito Turistico Chianti, due to its various features: the church, rectory, cloisters, and garden. The city of Siena is silhouetted to the west, behind a continuous succession of hills that stretch farther into the horizon.

After Pontignano, the road begins to descend, first gently and then with gradients well over 10%. You arrive at Ponte a Bozzone, where you should follow the signs for ‘Siena’; pedal uphill again for about a kilometre and then take the road that leads to the fortified village of Monteliscai.

The road towards San Giorgio a Lapi is now almost free of traffic, alternating between short climbs and flat stretches. Near the church of San Giorgio a Lapi, which stands high up on a hillock overlooking the first Chianti spurs, a section of dirt road begins, the second-to-last one that professional cyclists take, riding in the opposite direction, in the world famous ‘Strade Bianche’ race that starts and finishes in Siena. The unpaved descent of Colle Pinzuto, with rather challenging portions, calls for extra caution.


The church of San Giorgio a Lapi, also known as San Giorgino, dates back to 1109. Built by a certain Ranuccio, it was donated to the abbot of the monastery of San Pietro a Roti, and later to the monks of the Camaldolese order of Montegrimaldi, who extended their dominion to the land between Colle Pinzuto, Villa del Serraglio, and the Torrente Bozzone (Bozzone Stream). In the Comunello di San Giorgio a Lapi (or ‘all’Api’, as it is sometimes written), of which the church was a part, excellent wines were produced from the 18th century onwards; there was also a women’s convent.

The church continued to be a parish belonging to the Camaldolese until the middle of the 17th century when, by then in ruins, its care was entrusted to the parish priest of San Pietro a Monte Liscai. As with all other parishes, it was suppressed by the Leopoldine regulation of 2 June 1777.

It is along these last few kilometres of dirt road that one can admire the agricultural landscape of the countryside near the city of Siena, abounding in rows of trees, what remains of the old terraces and dry stone walls that once marked out properties and roads, and plots of vineyards and olive groves that still alternate with more or less extensive woodland.
When you reach the bottom of the valley, marked by the Torrente Bozzone, you will be on asphalt again. Take a right, uphill, and then descend to the outskirts of Siena. Porta Pispini is just over a kilometre further on.


The construction of Porta dei Pispini, historically known as Porta di San Viene (an error, however, since Porta San Viene, the oldest gate, is actually the arch that precedes it and gives access to Piazzetta Mario Cioni), was carried out between 1326 and 1328, most likely according to a design by Minuccio, or Muccio, di Rinaldo from Perugia, who was working in Siena at the time, together with his brother Francesco, on the construction of the Torre del Mangia. Consisting of an enormous tower with a wall in front of it, perhaps added in the second half of the 15th century, the fornix features a round arch surmounted by an aedicule which was frescoed between 1528 and 1531 by Giovanni Antonio Bazzi, known as Il Sodoma, with a representation of the ‘Natività con una Gloria di Angeli’ (‘Nativity with a Glory of Angels’). Only a few fragments of the painting, damaged by the elements, remain; they were removed in the 1970s and placed on the counter-façade of the Basilica of San Francesco. The door and the battlements were restored around the middle of the 19th century, even though the original battlements, ‘which were so majestic’, were destroyed in 1784, as witnessed by Pietro Pecci in the ‘Giornale Sanese’ (a veritable diary of things that occurred in Siena in the 18th century), who commented: ‘these being barbarous times for the city of Siena, one cannot describe anything but barbarous resolutions’.

The ‘New’ Station


On 25 November 1935, Siena’s new railway station was inaugurated, opening a new chapter of fundamental importance in the history of the area’s transport links. Even at the beginning of the 20th century the ‘old’ station (whose main building and mechanical workshop behind it are still standing at the beginning of Viale Mazzini) was deemed both inadequate to meet the needs of rapid connections and too cramped, since expansion of the structure was impossible.

ⒸRaimond Spekking

In 1914, the Ferrovie dello Stato (State Railways) approved the project to move the station to the valley below, where the line to Chiusi already ran, as the alternative options of Porta Ovile and Porta Romana had been rejected. Before starting the actual work, the site identified needed land reclamation and consolidation work, but this was brought to a halt by the outbreak of war. Once the war was over, funding was lacking and the site remained idle for a long time: the initial project itself was called into question, having become unsuited to the city’s changing needs. Finally, in 1931, the architect Angiolo Mazzoni, who at that time had designed several other stations in Italy, was commissioned to complete the Siena station. After some modifications (and delays), on 29 December 1933, the project was approved by the Municipality and the Superintendency with some final touches, such as the rectangular tower with the clock that was a sort of signature of the architect. Work was nearly completed in July and, during the course of the project, variations were introduced to simplify the side buildings in order to enhance the central body of the building. The new railway station was opened to the public as early as 18 October, although the inauguration did not take place until 25 November, in the presence of Minister Antonio Stefano Benni, local authorities, and the top management of the railways. The city was adorned with flags, the Sienese applauded the work, and coins were even minted to celebrate the event. In the minds of those who had conceived it, this architectural work aimed to reproduce, in a fresh and modern form, the characteristics of Palazzo Pubblico. Unfortunately, the elegant railway complex was largely altered during post-war reconstruction (the station was bombed on 23 January 1944, as was the Basilica dell’Osservanza).

“Caravaggio’, the Partisan Painter

Between May and June 1944, the Germans were preparing their retreat to northern Italy. The power of the Repubblica Sociale Italiana (Italian Social Republic), which had always been very fragile and only operated with the support of its Nazi ally, collapsed and the partisan factions took control of most of the province of Siena. Bruno Bonci, a young Sienese painter, although no longer old enough to be enrolled in the RSI militia, decided to join the Monte Amiata partisan unit, which also operated in the Chianti area, under the battle name ‘Caravaggio’. In Vagliagli, on 12 June 1944, the German troops, after yet another olive oil raid on the homes of some farming families, clashed with three partisans, one of whom was Bruno Bonci, who were waiting to ambush them near the village cemetery. Caravaggio was shot dead in the firefight. In his memory, a memorial stone was erected in Vagliagli, designed by the artist Maurizio Masini and unveiled in 1981, while a street in Siena bears his name.

Certosa di San Pietro in Pontignano

La Certosa (the charterhouse or Carthusian monastery), one of three in the Sienese territory along with Maggiano and the now vanished Carthusian


monastery of Belriguardo, was founded in 1343 by Bindo di Falcone Petroni after his project was approved by the then bishop of Siena Donosdeo Malavolti. Petroni commissioned Friar Amerigo, a Carthusian monk from Aquitaine, to build a monastery that could accommodate twelve monks and three converts. In 1353, Petroni made his will and left all of his estate to the Carthusian monks of Pontignano who, after the fire of 1478 and the damage suffered during the War of Siena in 1554–1555, when the complex was sacked and half-destroyed, had the complex rebuilt. Reconsecrated in 1607 by Archbishop Camillo Borghesi, important artistic projects date back to this period, such as the genuflecting Saint Romuald by Antonio Fanzaresi from Forlì, which can be admired in the small church, or the works of the Nasini brothers, Francesco Vanni, and other major artists of the time. Pontignano remained Camaldolese until 1810 when it was definitively abolished by Napoleon. Ecclesiastical activity was not interrupted until the parish of San Martino a Cellole was transferred to Pontignano. After various changes of ownership, it became the property of the Sienese Mario Bracci, a constitutional judge and Rector of the University of Siena, in 1959, who gave new importance to the monastery by transforming it into a university college. Today, Pontignano is used for conferences and accommodation, and the guest quarters comprise the ancient cells of the monks, which have been converted into flats.


Once a castle of the Sienese Republic, Monteliscai is mentioned in documents as far back as 1101, when the priest of the church of San Pietro (which still exists today and bears a handsome monogram of San Bernardino on the entrance door) offered its patronage to the Camaldolese Abbey of San Pietro a Ruoti (in the Val d’Ambra, in the diocese of Arezzo). In 1203, thirty-nine heads of families (and from this number the size of the settlement within the walls can be deduced), together with those who lived in the other fortifications situated towards the northern limits of the Sienese contado (territory in the countryside), partook in the oath by which the Sienese and Florentines sought, even then, to settle a dispute over the boundaries of their territories.


Monteliscai often found itself in the middle of the belligerent ‘skirmishes’ between Siena and Florence, so much so that in 1229 it was occupied by the Florentines, even if for a short time and to the surprise of the Sienese citizens when the chroniclers wrote: ‘Despite its strong, high, and nearly inaccessible position to the enemy, as it is planted on the highest peak of the mountain, and crowned on all sides by precipices and crags, it succumbed, albeit temporarily, on 19 September 1229, to the force of the soldiers of the Republic of Florence’.

Monteliscai was attacked, again by the Florentines, in 1479, during the war against the Sienese and Aragonese, then allies.

When you visit Monteliscai (because you are going there, aren’t you?), you will see that the current buildings were partially built on the ruins of the ancient walls, the perimeter of which remains in an optimal state of repair and still has the original access gate, the lower part of which was damaged around the middle of the 20th century to facilitate the passage of farm carts.

In short, the fortress of Monteliscai was damaged more by farmers than by wars.



I Comuni di Terre di Siena