Visiting Val d’Orcia: a 100 miles Journey visiting Pienza, Montalcino, S. Quirico & Much More (4K)

In this video, we embark on a 160 km (100 miles) cycling and walking adventure through the heart of Tuscany’s Val d’Orcia, a region celebrated for its rolling hills, golden fields and timeless villages. Pedaling along cypress-lined lanes and strade bianche (the classic white gravel roads), we traverse a landscape so enchanting that it’s protected as a UNESCO World Heritage site. From medieval hilltowns to soothing hot springs, join me in experiencing the sights, flavors, and rhythms of this Tuscan paradise.

ITINERARY HIGHLIGHTS:

GPX Route: For those interested in the exact route and elevations, you can download the GPX track of this 160 km itinerary here: https://drive.google.com/drive/folders/1Aobis5pTuVVrOndNmb7nq82eL1sZxEws?usp=sharing. Feel free to use it as a guide for your own adventure!

Here’s a summary of the key stops on this Val d’Orcia bike/walk tour (total distance ~160 km – 100 miles), featuring eight unforgettable locations:

– Montepulciano – The grand finale of our tour is Montepulciano, a majestic hill town renowned for its Renaissance architecture and robust Vino Nobile red wine. We conquer a final uphill push to reach Montepulciano’s Piazza Grande, surrounded by stately palazzos and a historic well. Here, at the highest point of our journey, we celebrate with a well-earned glass of Vino Nobile di Montepulciano.

– Monticchiello – A postcard-perfect stone village perched on a ridge, offering one of the most breathtaking panoramas in all of Val d’Orcia. To reach Monticchiello, we follow a winding road lined with cypress trees that has become emblematic of Tuscan imagery. Inside this quiet hamlet, time seems to stand still – there are flower-filled balconies, a tiny church, and even an old theater where locals famously perform community plays each summer. Monticchiello’s serene atmosphere and sweeping views make it a hidden treasure along our route.

– Bagno Vignoni – A tiny spa village unlike any other, built around a steaming thermal spring. In the center of the hamlet lies a large hot spring pool where water has bubbled since Roman times. We dip our tired feet in the therapeutic waters that once soothed ancient pilgrims and even St. Catherine of Siena. Surrounded by stone archways and a medieval mill, Bagno Vignoni feels like a dream – a place where time slows down to the sound of gentle thermal streams.

– San Quirico d’Orcia – A medieval town on the Via Francigena, known for its well-preserved historic center and the Horti Leonini – a 16th-century Italian Renaissance garden. Following an ancient pilgrim route, we arrive in San Quirico to stroll its narrow stone streets and relax under the shaded loggias. Just outside town, the sight of an iconic cypress grove emerging from the rolling fields signals that we are truly in the postcard-perfect Val d’Orcia.

– Pienza – Often called the “Ideal City of the Renaissance,” Pienza was transformed by Pope Pius II into a perfect town in the 15th century. Now a UNESCO World Heritage site, this jewel of Val d’Orcia greets us with graceful palaces, a beautiful piazza, and cobbled lanes with names like Via dell’Amore (Love Street). We pause to sample pecorino di Pienza cheese in little shops (the town’s famous gourmet product) and admire views from Pienza’s panoramic terraces. The blend of history, architecture and mouth-watering aromas here truly captures the essence of Tuscany.

– Montalcino – At the heart of Brunello wine country, this hill town demands a steep climb but rewards us grandly. We pedal past sunflower fields and vineyards on the slopes of Monte Amiata, then ride up to Montalcino’s 14th-century fortress dominating the skyline. Inside the fortified walls, we wander cobbled lanes and perhaps toast with a glass of the legendary Brunello di Montalcino. The panorama from the ramparts – endless hills striped with vines – is Tuscany at its finest.

– Buonconvento – A welcoming medieval village whose name comes from Latin bonus conventus, meaning a “happy, fortunate community”. Once a rest stop on the ancient Via Francigena pilgrimage route, Buonconvento charms with its brick walls, quaint streets and local museums.

– Murlo – A tiny hilltop hamlet with roots tracing back to the Etruscans. We cycle through dense oak woods and quiet backroads near Murlo, enjoying the peaceful seclusion of this lesser-known gem. Here, you find rustic stone houses and an Etruscan archaeology museum.

JOIN THE ADVENTURE!
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