Follow me on a breathtaking journey through the picturesque Val d’Orcia, exploring the enchanting medieval towns of Montalcino, Castiglione d’Orcia, and Radicofani. This itinerary will guide you through these historic gems, ensuring you indulge in their culinary delights and stay in charming accommodations. Buckle up for a memorable trip across three towns that will take you back to the days of the Middle Age thanks to their architecture, the walls that still surround them – at least in part – as of today, the net of streets and alleys that feel absolutely unique, with views and landscapes that will leave you speechless.
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Montalcino, Castiglione d’Orcia, and Radicofani are art, history, nature, excellent food and wines. They are pure Val d’Orcia.
The Road Trip
From Montalcino to Castiglione d’Orcia (25 minutes by car, 24 km): Take the SP14 road southwards from Montalcino towards Torrenieri, then follow the SS2 road (Via Cassia) then the SP323 road (you’ll have to turn right about 400 metres after Bagno Vignoni, just follow the signs and you’ll be ok), which will lead you directly to Castiglione d’Orcia.
From Castiglione d’Orcia to Radicofani (26 minutes by car, 21 km): From Castiglione d’Orcia, take the SP323 road until you reach the SS2 road (Via Cassia), then follow the signs to Radicofani on the SP478 road. This scenic drive offers stunning vistas of the Val d’Orcia countryside.
Montalcino: A marvellous fortress in the middle of Brunello’s vineyards
Montalcino, famed for its world-renowned Brunello wine, is a medieval marvel perched on a hilltop. This town offers panoramic views, ancient streets, and a rich history. Brunello di Montalcino and Rosso di Montalcino red wines taste so much better, if savoured at a table along the town’s characteristic streets, while eating a “tagliere” (literally, a wooden tray) filled with local ham, salame, finocchiona, and cheese.
When in Montalcino, I recommend a visit to both the Civic and Diocesan Museum of Holy Arts (Museo Civico e Diocesano di Arte Sacra) and the Temple of Brunello Museum, but there are so many places that deserve your time and attention… And I’m not even mentioning wine-tasting in local wineries. They’re just too good to miss such an experience.
The fortress: The Montalcino Fortress, built in the 13th century, stands as a testament to the town’s strategic importance. With its imposing walls and towers, the fortress offers stunning views of the Val d’Orcia countryside.
Eating Spots:
- Osteria di Porta al Cassero
- Re di Macchia
- Enoteca la Fortezza di Montalcino
- Ristorante Boccon DiVino
Accommodations:
Castiglione d’Orcia: Two Fortresses Double the Medieval Magic
Castiglione d’Orcia is a charming medieval town nestled in the rolling hills of Tuscany. Known for its two fortresses, it offers a glimpse into the past with its narrow streets and ancient architecture.
When in Castiglione d’Orcia, don’t miss the Sala d’Arte San Giovanni, a small museum which is absolutely worth a visit. And take a detour to Bagni San Filippo, for its incredible hot springs.
The two fortresses in Castiglione d’Orcia:
Rocca di Tentennano – It was built in the 9th century, and still today is one of the silent giants that dominate the Val d’Orcia with their imposing figure rich of history.
Rocca Aldobrandesca – This fortress built in the 13th century sits right in the middle of the town, and walking along the walkways on top of the walls is an incredible experience that opens up new views of the Val d’Orcia. Unmissable!
Eating Spots:
Accommodations:
Radicofani: A Fortress in the Sky
The whole ancient part of the town of Radicofani is a gem, and you will have a fantastic time just walking along its characteristic streets and admiring the marvellous buildings. Just out of Radicofani there’s the Bosco di Isabella, a romantic garden that combines the natural beauty of the area with carefully constructed paths, dry stone walls, bridges and water points.
The fortress: The Rocca di Radicofani dominates the landscape, towering over the town. Built in the 10th century, this fortress was once home to the infamous outlaw Ghino di Tacco, a local Robin Hood figure. The views from here are simply breathtaking.
Eating Spots:
Accommodations:
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