Exploring the Val d’Orcia: Montepulciano, Pienza, San Quirico, Montalcino, Castiglione d’Orcia and Bagno Vignoni

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The Val d’Orcia is a paradise for the eyes, a valley so beautiful it’s been declared a UNESCO World Heritage Site. With a drive of about 80 kilometres, it’s possible to be enchanted by all parts of the valley in a single day.

From Poggio al Vento, you can choose many roads to reach the towns of the Val d’Orcia, but we suggest a panoramic tour of the valley so that the trip becomes a unique experience among the colours and atmospheres of the Tuscan landscape. The route is lovely by car and even more incredible for motorcyclists, with broad curves and excellent roadholding.

The first stop in our Val d’Orcia itinerary is Montepulciano, about 25 kilometres from Poggio al Vento. It’s a historical medieval and Renaissance town, with its churches and the Medici fortress restored by Antonio da Sangallo the Elder. The area is known for its Vino Nobile di Montepulciano, which can be tasted in any enoteca (wine shop). This is a town that gives great attention to art and culture, with numerous exhibitions every year, particularly those recently dedicated to illustrators and cartoonists who have lived in Montepulciano, such as Andrea Pazienza. Part of the film The Twilight Saga: New Moon was shot in Montepulciano and the town offers fans a guided tour to the places featured in the film.

The tour continues to Pienza, about 13 kilometres on. This town, the jewel of the Val d’Orcia, will enchant you with its 15th century architecture and its position on the summit of the lovely hills that have made Tuscany famous throughout the world. In spring and summer, you’ll remain breathless at the spectacular views from the balcony overlooking the town walls. The characteristic trapezoidal town square is framed by many masterpieces of the architect Bernardo Rossellino, such as the Piccolomini Palace with its beautiful garden, the Borgia Palace and the Cathedral. With its many shops selling crafts and typical food products, Pienza is the ideal place to stop for lunch; wine and pecorino (sheep cheese) are the specialties that shouldn’t be ignored.

The third stop of the tour is San Quirico d’Orcia, 10 kilometres from Pienza, the oldest town of the itinerary with Etruscan origins. A walk through this charming town will lead you to the Church of San Francesco and the Horti Leonini realized in 1580 by Diomede Leoni, a classic example of an Italian garden.

The fourth stop is Montalcino, 15 kilometres from San Quirico. This medieval town is famous for its Brunello wine and there are very many enoteche where you can taste vintage wines for true connoisseurs. In July, the Jazz & Wine Festival will please lovers of wine and music in the unique setting of the fortress. The castle conserves the outer walls, which can be visited and provide a panorama of the vineyards surrounding Montalcino.

The fifth stop, Castiglione d’Orcia, seems to be the top of Tuscany. Indeed, during the tour it’s impossible not to notice a perfectly conserved fortress towering above the entire Val d’Orcia only 20 kilometres from Montalcino. The town of Castiglione d’Orcia is a well-preserved example of characteristic medieval architecture that shouldn’t be missed. The Tentennano Fortress dominates the valley and seems to touch the sky.

On the return trip, if you’re still not satiated with beautiful towns, the ideal stop for an aperitif is BagnoVignoni.

The main square is a basin of thermal water which has made BagnoVignoni a famous spa since Roman times.

There’s a good view of the just-visited Fortress above.

The last view of the beautiful Val d’Orcia is on the road that leads back to Poggio al Vento.

Itineraries and travel times by car:

From Poggio al Vento, go to Foiano and take the road to Bettolle, and from there to Torrita di Siena; follow the signs for Montepulciano

From Montepulciano, take road SS146 for Pienza

From Pienza, continue on SS146 for San Quirico D’Orcia

From San Quirico D’Orcia, take Via Cassia in the direction of Montalcino

From Montalcino, take SS323 for Castiglione D’Orcia

From Castiglione D’Orcia, take SS323 for Bagno Vignoni

To return to Poggio al Vento from Bagno Vignoni, take SP15 to Pienza and then Torrita di Siena, Bettolle, Foiano and Pozzo della Chiana.

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