“The Val d’Orcia is an exceptional reflection of the way the landscape was re-written in Renaissance times to reflect the ideals of good governance and to create an aesthetically pleasing picture”: this was part of the criterion for UNESCO’s designation of Val d’Orcia as a World Heritage site in 2004. If you were to ask an American or someone from Northern Europe to describe their perfect vision of the Italian countryside, they would almost certainly mention one of the images that most distinguish this region, namely the famous cypress-lined roads criss-crossing through rolling hills, and a landscape dotted with beautiful villages that display their unmistakably Tuscan design. Pienza more than deserves its attribution as the ‘ideal city’ of Enea Silvio Piccolomini, otherwise known as Pius II, who served as Pope from 1458 until his death in 1464.
In many senses, Val d’Orcia is pure poetry. Although the soil is arid, it remains at least partially suited for producing the outstanding wines that have garnered international recognition and stellar prices, such as Brunello di Montalcino DOCG. This is a testament to effective land management and regulations that prioritise high quality and the identity of a well-defined area. Additionally, the domain is rich in culinary delights, with premium meats, game, cured meats and DOP cheeses like Pecorino di Pienza, along with honey, saffron, extra virgin olive oil and both white and black truffles, which are harvested at night in the woods.
The Crete Senesi, memorable for its unique clay hills that in places resemble lunar landscapes, has, like the Chianti trail, recently become a prime location for both professional and amateur cycling events, such as the Strade Bianche and Eroica. The latter, in particular, is evolving into a veritable lifestyle, promoting slow, eco-friendly and social tourism that harkens back to the past in the form of vintage bicycles and attire, while celebrating the winning synergy between stunning vistas, physical fitness and the sampling of local delicacies. The province of Siena is committed to preserving and enhancing these dirt tracks and to ensuring they do not get covered with asphalt.
Our journey begins in Siena, heading south on state road Statale 2, the ancient ‘Via Cassia’ and part of the renowned Via Francigena, which historically connected Northern Europe to Rome and the Holy Land. This route has seen a revival since the Jubilee of 2000, attracting modern-day pilgrims seeking peaceful and spiritually enriching journeys. Following the course of the Arbia River, you will now enter the Crete Senesi region, the name given to the part of the world southeast of Siena. The first historical residence on our itinerary is to be found in Monteroni d’Arbia. Castello di San Fabiano has all the characteristics of a small independent hamlet, featuring a 12th-century tower, a main villa with attached farm buildings and a church dating back to 867 AD, dedicated to Saint Fabian. This property is owned by the Fiorentini family and currently serves as a wildlife repopulation area. Accommodation in the form of suites is available inside the castle, complete with a swimming pool and facilities for hosting private events.
The Villa e Fattoria di Radi lies not far away in Radi. This villa and farmhouse occupy the site of an ancient castle built by the Sienese to defend their city, and was formerly the residence of a Captain dispatched there by the City of Siena. After its destruction by the Florentines, the present Villa was constructed on the castle’s ruins in the 17th century and has been in the possession of the Bichi Ruspoli Forteguerri family ever since. The estate includes a 17th-century chapel and a terraced garden on the medieval castle walls. Currently, it operates as an organic farm and hosts private events and weddings. Nine holiday apartments with panoramic views over the Crete Senesi are available for guests, who also have the opportunity to sample local products at the on-site snack bar, Sapori di Radi.
Returning to the Cassia road in the direction of Buonconvento, you can include a stop at our third historical residence in the village of Curiano, appropriately called Villa Curiano, which belongs to Marchesa Isabella Gaetani di Canossa and overlooks the 400-hectare organic farm. The Villa has recently been restored and now provides eight guest bedrooms. Visitors can enjoy the swimming pool and relaxing garden, while soaking up the spectacular views of the Crete Senesi.
En route for Montalcino, schedule a break in Buonconvento, a village recognised by the Touring Club as being one of the most beautiful in Italy. This charming spot was extremely significant for pilgrims and merchants taking the Via Francigena to Rome, the heart of Christianity. In this reassuringly named place (Buonconvento derives from the Latin bonus conventus, meaning ‘happy, fortunate community’), travellers would stop off for a rest and to recharge their batteries. This tradition continues today, with passing visitors welcomed to enjoy lunch or dinner in one of the various taverns offering a modern twist on traditional cuisine. An absolute must-visit is the Abbey of Monte Oliveto Maggiore, the seat of the Abbot General of the Olivetan Benedictine order, founded in the 14th century by Saint Bernardo Tolomei from Siena. On display in the monastery are artistic treasures, such as frescoes by Signorelli and Sodoma, and wooden carvings by Fra Giovanni da Verona. After Buonconvento, head toward Montalcino via Provincial Road 34, which leads past Bibbiano and its castle, before arriving at another historical residence, Castelnuovo Tancredi. Set within a vast 600-hectare estate, this villa is an excellent base from which to explore the Brunello wineries: it provides nine guest suites for overnight stays, and additionally has accommodation in a. number of farmhouses on the estate, with amenities including a swimming pool, a tennis court and a wellness spa equipped with a gym and sauna. Returning along Provincial Road 103, cross the Ombrone River, passing the Castiglion del Bosco Golf Club on the way for Montalcino.
As the entrance to one winery is followed by another, you will eventually reach the town of Montalcino, where you can not only purchase the finest vintages of Brunello and Rosso wines, but also wander through its old centre, starting at the Sienese fortress and culminating your walk at the Temple of Brunello in the complex of Sant’Agostino. This site features a recently restored church, the Civic and Diocesan Museum and a bistro serving excellent dishes where you can sample all the wines of the territory.
There is certainly no shortage of options for those seeking to indulge in a fine meal, as Montalcino’s renown and reputation have led to numerous restaurants achieving fame and even receiving Michelin stars. If you are keen to diversify your experience beyond wineries, a trip to one of the local dairies in Val d’Orcia is highly recommended. Once you have left Montalcino, consider taking a cultural and spiritual detour to the Abbey of Sant’Antimo, a striking Romanesque structure dating from the 8th to the 13th centuries, notable for its exquisite French-inspired architecture and remarkable alabaster onyx features.
As you drive between Montalcino and San Quirico d’Orcia, the most iconic image of Val d’Orcia will suddenly appear before your eyes: a solitary grove of cypress trees perched atop a gentle hill in the locality of I Triboli. The colour of the soil transforms dramatically with the seasons, reflecting the crops that mature throughout the year. San Quirico d’Orcia has a medieval layout, with two arresting Romanesque churches at either end. In the town centre, be sure to visit the Horti Leonini, a lovely 16th-century public garden designed to refresh weary travellers, and Palazzo Chigi, a 17th-century building that now serves as the town hall. On the main street is another historical residence that can be visited upon request: the Casa dell’Abate Naldi was commissioned in the 17th century by Matteo Naldi, a physician and scientist from Siena. This property offers rental accommodation and provides an ideal setting for photoshoots. Cooking classes are held in the ground-floor kitchen, and the courtyard with its central well overlooks a small, atmospheric hanging garden, perfect for an aperitif on the occasion of a special event. Just a short drive from San Quirico d’Orcia, the family that owns Casa dell’Abate Naldi also runs an organic farm and the Agriturismo Il Rigo, providing lodging in an ancient travertine farmhouse dating back to the 16th century.
Bagno Vignoni, a hamlet of San Quirico d’Orcia, boasts a unique thermal spring, which flows from a monumental bath around which the inhabited area has developed and cascades dramatically into the Orcia River. Should you be looking to combine your trip with thermal treatments, we highly recommend you stay here at one of the hotels with indoor pools.
Our next destination is the historical residence Villa La Foce. Constructed in the late 15th century as a resting point for pilgrims and merchants, it is today a highly regarded venue for private events, and a charming relais. Its enchanting garden is particularly appreciated, with its blend of Italian and English styles. It was designed between 1924 and 1939 by the Marchesi Antonio and Iris Origo in collaboration with English architect Cecil Pinsent, who is regarded as its master creator. The Origo family continues to be a significant cultural and literary influence in the region, following in the footsteps of author Iris, particularly through their patronage of the ‘Incontri in Terra di Siena’ festival of musical encounters.
Leaving La Foce, travel along the scenic secondary road towards the Val di Chiana valley, which will being you to Montepulciano, often referred to as the ‘Pearl of the 1500s’ and a notable production area for Vino Nobile di Montepulciano red wine. Birthplace of Medici poet Il Poliziano, the town possesses an impressive architectural landscape that alternates medieval buildings with a row of beautiful Renaissance palazzos, giving it the appearance of an authentic open-air museum. It is well worth climbing to the top of the steep Corso to reach Piazza Grande, with its Cathedral and Town Hall, which replicates Palazzo Vecchio in Florence in miniature, as well as 16th-century buildings designed by Sangallo, including Palazzo Contucci and Palazzo Nobili Tarugi. Close to the square, the fortress, which rests on an Etruscan site, houses a wine shop and an exhibition space. Palazzo Neri Orselli is home to the Civic Museum, whose collection ranges from archaeological finds to medieval, Renaissance and modern paintings, together with an incredible array of ceramiche robbiane, intricately designed ceramic pottery inspired by Andrea della Robbia. The local gastronomic scene in Montepulciano is vibrant, to say the very least. If you would like to sample the Nobile or Rosso wines, you will be spoiled for choice at one of the many underground wineries in the town, or you can enter one of the more than two hundred wineries sprinkled all around which belong to the Vino Nobile Consortium. We suggest you pay a visit to the elegant Caffè Poliziano. In operation since 1868, the café, which also has a restaurant proposing traditional dishes, is a proud member of the ‘Locali Storici d’Italia’ or ‘Historic Establishments of Italy’ association. No trip to Montepulciano would be complete without entering the hallowed Temple of San Biagio, located just outside the town. This masterpiece from the sixteenth century was designed by architect Antonio da Sangallo the Elder.
Our itinerary now leads us towards Pienza, taking a detour through the fortified village of Monticchiello, with its community cooperative Teatro Povero. Literally signifying ‘Poor ‘Theatre’, this cultural initiative has revitalised a village once heavily in decline during the 1960s. Pienza is arguably the best-known town in Val d’Orcia and definitely warrants a comprehensive tour. Piazza Pio II, the architectural realisation of the ideal Renaissance city, bears the name of its creator, a pope born there in the 15th century who teamed up with Florentine architect Bernardo Rossellino for its design. The cathedral, located at its centre, is flanked by two alleyways that literally and figuratively transport the panoramic valley view into the square. On either side of the piazza are Palazzo Piccolomini, a historic papal residence that has become a house-museum, and Palazzo Borgia, where the small yet precious Diocesan Museum is situated. Corso Rossellino and its side streets contain a variety of quality shops selling cured meats, cheeses and other local specialities, as well as handcrafted items made from wrought iron, leather and ceramics, alongside textile woven products and artistic, recycled goods.
In terms of overnight accommodation, there are a couple of historical residences just a short distance from the town: one is the fortress of Palazzo Massaini, once owned by the Piccolomini family, whose Podere La Pieve is a renovated agriturismo farmhouse, complete with an infinity pool and offering outstanding views of the valley. Another option is Borgo Sant’Ambrogio, comprising a main building dating back to the 16th century and a series of more recent structures, now converted into a resort with bedrooms and apartment. Services include a restaurant, a conference room and a swimming pool for guests.
Continuing along Provincial Road 71, you will pass through the villages of Castelmuzio and Montisi, after which you will reach San Giovanni d’Asso, a place that is famous for its prized white truffles, where an annual market is held on the two central weekends of November. This is the location of Villa La Consuma, which features a large terrace garden and swimming pool, originating right back to the 14th century when it was part of the structure surrounding the Castle of San Giovanni d’Asso. Today, the entire manor house can be rented out with its private swimming pool. It is also possible to organise dinners, cooking classes and exclusive tastings of wine and truffles in the ancient cellar. In San Giovanni d’Asso, don’t miss the immersive experience at the woodland park and garden called Bosco della Ragnaia, created by the American artist Sheppard Craige in the 1980s, which presents philosophical trails steeped in both mysticism and irony.
The final stop on this itinerary through the Crete Senesi is Borgo Lucignanello Bandini in Lucignano d’Asso, handed down from generation to generation by the Piccolomini family for the last six hundred years and recently restored as a historical residence. This is the perfect place to wind down in one of the self-contained lodgings where you can relish the serenity of the Tuscan countryside, visit its winery and taste the extra virgin olive oil produced on-site. In the warmer months, you can relax in the infinity pool on the hillside, feasting your eyes on the magnificent landscapes and unforgettable sunsets.