Soft, rolling hills, lone cypress trees dotting the peaks, white roads in the countryside that run for as far as the eye can see. This the Val d’Orcia, waiting to be discovered on a five-day walk. The itineraries proposed here are easy, without technical difficulties and require minimal climbing, and all of them propose visits to the historic centres of San Quirico d’Orcia, Montalcino, Pienza, Castiglione d’Orcia and Radicofani, which, together with the Val d’Orcia Artistic, Natural and Cultural Park, are continuously aimed at protecting the immense historic and natural patrimony of the territory to the south of Siena and at promoting its typical products.
It’s impossible to be indifferent to such a landscape. Rich in colours and atmospheres, scents and flavours, the Val d’Orcia has always seduced its visitors. In this puzzle of art, history and nature waits a vacation marked by authenticity. In the prosperous link between agriculture and environment, the Val d’Orcia protects and promotes high-quality products like oil, wine, pecorino cheese, saffron and honey. One of the best-preserved sceneries in Tuscany, tourists can retrace historic routes, including the via Cassia and via Francigena, the latter of which has been walked for centuries by pilgrims driven by strong spiritual motives to undertake a journey to the centre of Christianity and pay tribute to the tomb of St. Peter.
In one of the best-preserved landscapes in Tuscany, the day begins with a visit to Pienza. The most precious gem in this ideal city commissioned by the great Humanist Silvio Piccolomini, inspired by the architectural principles of Leon Battista Alberti, is piazza Pio II, crowned by Palazzo Piccolomini, the Cathedral of the Assunta and the beautiful fountain, strictly designed in the Renaissance style. Harmonious and proportionate as a whole: this is the impression you’ll have as you walk the village’s streets, shielded at the top of the hill. Begin this pleasant stroll from the northern door, crossing the quiet and relaxing Vitaleta countryside along the dirt track that leads from Pienza to San Quirico d’Orcia.
A brief detour will give you the chance to admire one of the most famous symbols of the Val d’Orcia: the Chapel of the Madonna di Vitaleta atop a small hill, for which there are no words to describe its immense beauty. From the late-Renaissance church, continue your walk through the wavy landscape characterized by ears of wheat and home par excellence to pecorino cheese and saffron. At the Commenda farm, leave the road behind you and turn to the left on a trail that leads to a trench running parallel to the asphalt road on the right. You’ll then come to another white road that climbs up the hill to Pienza. From the town, the view ranges across the Crete, where herds of sheep can be seen roaming, the source of the famous Pienza pecorino and fresh cheeses like “raveggiolo” and “marzolino”.
The second day is dedicated to not just the allure of nature, but also historic, artistic and monument-related interests. One of the best introductions! In Bagno Vignoni on cold winter nights, the medieval pool releases wisps of water vapour. The thermal waters were known and appreciated by the Etruscans and especially the Romans, and it was here that Lorenzo the Magnificent attempted to alleviate his gout-induced pain. The 49x29 metre pool sits in the centre of the piazza, closed on three sides by a wall 1.5 metres high and the Santa Caterina portico on the fourth side.
From the small village, which has preserved its original structure from the 1300s, a white road runs up toward the hamlet of Vignoni, home to a castle. The spirit of the place leaves visitors fascinated by its historic walls: it’s difficult to pull your gaze away from the picturesque gate “that watches the valley”. Further up, you’ll arrive at a white road coming from San Quirico d’Orcia to the left. A consecrated chapel announces your arrival at the mighty, private Ripa d’Orcia castle, transformed into a comfortable country residence after a detailed restoration. The position is dominating, the view unique: below, you can see the Orcia flowing through its canyons.
A CAI trail allows you to reach and pass over the creek, after which you will climb up to the fortified village of Rocca d’Orcia, which once welcomed Catherine of Siena (God laid me down on this rock, and from all sides, the winds lash at it”). Once you’ve had the chance to admire the large polygonal cistern in the central piazza, the next stop is the nearby Rocca di Castiglione d’Orcia, a panoramic terrace overlooking the valley. Lorenzo di Pietro was born in the village, a 15th-century artist of the Sienese school, and from here you can descend along a trail that leads to Bagno Vignoni, closing the circle.
San Quirico d’Orcia is one of the best-preserved historic centres in the valley. The defense walls enclose valuable monuments, like medieval houses, Porta dei Cappuccini, Palazzo Chigi, Palazzo Pretorio, Horti Leonini and Collegiate Church, the last of which is the town’s most precious gem and conserves superb portals with Romanesque sculptures and low-reliefs by the great sculptor Giovanni Pisano.
The surrounding countryside is marked by clayey, rolling hills and the horizon opens towards rows of cypress trees, small farms, vineyards, olive groves and cultivated fields. Take a walk through this splendid water painting, crafted by man and nature. From the Collegiate Church of Santi Quirico e Giulitta, take the road to Riguardo; after a staircase, go under an overpass, where the trail will become a typical white road as it continues into the rural landscape.
At a crossroads, near an abandoned farmhouse, keep to the right; the main route will come to a wood and you’ll take the road to the left as it descends downhill. Once you’ve come out the other side of the wood, there will be a small pond on the right, after which you’ll come to a road on the right that leads to some farm buildings.
The next stop is one of the most photographed spots in the whole Val d’Orcia: the colours of the Sienese landscape come perfectly presented in a sort of natural Pinacoteca, where the harmony of the various tones and the plays of light on the hills can be discovered with every change in perspective. Continue past a circle of cypress trees, eventually reaching the town of “I Triboli” on a small hill that dominates a stretch of the via Cassia to the south, where you can photograph the posing “San Quirico d’Orcia cypresses”. This is one of the most reproduced images in the world.
Thanks to an underpass, you can move beyond the Cassia and continue toward the town of Bellaria: the dirt road merges with provincial road n. 71, which you’ll abandon immediately as you turn to the right around the houses in the hamlet. To return to San Quirico d’Orcia, head south-east until you reach provincial road n. 14.
The most celebrated Italian wine, the Brunello di Montalcino, almost overshadows the historic monuments of the last fortress of the Republic of Siena, rising atop a hill dotted with olive groves and vineyards. And yet, there are many artistic and monumental treasures preserved in Montalcino: the imposing Rocca Senese, Palazzo dei Priori and the nearby Gothic portico, the Churches of Sant’Egidio and Sant’Agostino and the Musei Riuniti, the town’s art museums.
After visiting the medieval centre and the fortress, hop in the car to explore the short distance (10 kilometres) between Montalcino and the splendid Abbey of Sant’Antimo, a Romanesque masterpiece perhaps founded by Charlemagne during the Holy Roman Empire (9th century).
Begin the hike in a meadow, amidst centuries-old olive groves and against a background of wooded hill, but not before visiting the Olivetan monastic complex, comprising the stunning plays of light in the church’s central nave, the Carolingian chapel, the crypt, the upper portico, the monks’ pharmacy and the San Benedetto vegetable garden. The trail leaves one of the most important Benedictine sanctuaries in central Italy behind as it climbs up toward the historic village of Villa a Tolli (532 m), a resting point for pilgrims coming from the abbey.
The itinerary continues counter-clockwise towards Ventolaio – a detour leads up to Poggio d’Arna – through the vast landscape of the Valle di Sant’Antimo and the majestic Monte Amiata, returning to the starting point along the white roads. A mystical atmosphere surrounds this place marked by peace and silence.
To the south of Siena, the landscape is always changing: a special autumn light ignites the ochre tones of the ploughed fields, and in the summer, the golden colour of the ears of wheat is set alight. Such a splendid panorama can be admired from above at the Radicofani Fortress, an important symbol for tourists along with the façade of Palazzo Pretorio (dotted with travertine coats of arms of Sienese Podestà) and the stunning terracottas by the della Robbias at the Churches of Sant’Agata and San Pietro Apostolo. Artistic attractions pass you by every step of the way as you follow the dirt roads and long-trekked paths.
Start your walk from the nearby village of Celle sul Rigo, with a perfect view of the austere fortress in Radicofani. The white road descends toward the south-east and winds through rolling badlands until you come to a path on the right that leads to Celle sul Rigo, which you can cross over around the La Novella farm. The route now merges with two important roads: the via Cassia and the via Francigena, which will accompany you to the foot of the Radicofani hill. When you’ve reached the top of the rocky cliff and visited the historic centre, continue along a brief stretch of the way you came, then move onto the white road that leads down into the Valle del Rigo and returns to Celle.