There’s a special valley south of Siena, a place where dreams are born. This place is the Val d’Orcia. A land where nature and man have come together to create a true paradise on earth. And in this area, whose beauty has been immortalised by artists and poets, you’ll find some of the most picturesque small towns in the whole of Tuscany.

Expect soft colours and a mellow, soothing atmosphere. The natural scenery, with vast wheat fields and lines of cypress trees is at times quite otherworldly. The local sandstone used for the buildings gives the towns a special soft light that’s almost luminous. It creates vistas and an atmospheres that are both breathtaking and quite moving.

=> Discover the wonders of the Val d’Orcia !

5 Picturesque small towns in the Val d’Orcia

Pienza, the “ideal city”

Pienza is the queen of picturesque. And its story seems straight out of a fairytale, the result of a Pope’s dream. Silvio Piccolimini was born right here in Corsignano (Pienza’s original name) and his ambition was so great that, when he became Pope in 1458, he employed one of the most notable architects of the Renaissance to re-imagine it. The idea was to covert the simple Medieval village into an “ideal city’, whose beauty and geometrical proportions would reflect the humanist principles that were trending at the time.

The graceful Cathedral square is the core of the town. For some stunning views of the verdant valley, walk to the street behind the Cathedral or visit the Piccolomini Palace’s garden. Along the main street Corso Rossellino you can find plenty of shops selling the local (and delicious!) pecorino cheese.

Check out this Private Full Day Tour of Pienza & Montalcino, the perfect way to round off your trip to the Val d’Orcia. You’ll visit the Val d’Orcia and taste some local cheeses and other traditional products along the way! Departure from Siena.

Pienza, the Cathedral Square

San Quirico d’Orcia. A Romanesque beauty

We simply adore this small town in the Val d’Orcia, and though it has long since been ‘discovered’ by tourists, San Quirico d’Orcia still feel pretty authentic. People here are friendly and there’s a relaxed atmosphere in the air. Perhaps its most striking sight is the ancient church, the Collegiata whose fantastical sculptures on the portal and weathered lions guarding the entrance, lend it an aura of magic and mystery.

Walking around the streets of this town is guaranteed to put anyone in a good mood. The colour of the stone, the traditional shops, the ancient buildings, all contribute to create a delightful effect.

And talking about picturesque, a few kms from San Quirico stands one of the most iconic sights of the Val d’Orcia, the Vitaleta Chapel, perhaps one of the most photographed corners of Tuscany.

=> See our Scenic Road Trip in the Val d’Orcia, that includes the Vitaleta Chapel.

San Quirico d’Orcia – photo @Lovefromtuscany

Bagno Vignoni, a picturesque spa town

Very close to San Quirico you find the lovely Bagno Vignoni, famous for its thermal waters since Roman times. The main square, aptly named Piazza delle Sorgenti (‘Spring Square’) is made of a 16th century stone basin which collects the water that comes from the subterranean source (aquifer) of volcanic origins. The stone buildings reflect themselves in the water, creating an atmosphere of timeless beauty.

This spa town in the Val d’Orcia has seen many honourable guests, from Pope Pio II to Lorenzo the Magnificent. Today it’s still a popular tourist destination, with many spa resorts nearby and a free pool of thermal water where you can have a dip, Parco dei Mulini.

picturesque villages in tuscany
Bagno Vignoni – photo @alefolsom on pixabay

Castiglione d’Orcia, land of ancient fortresses

The stone paved streets and small squares of Castiglione d’Orcia transport the visitor to another time of knights and legends, a time where powerful families and free cities, or Comuni, would fight over this territory. The ruins of the fortress that look over the small town are a reminder of this turbulent past.

You can visit the two Romanesque churches of Santa Maria Maddalena and Santi Stefano e Degna. For more Medieval delights, visit nearby Rocca d’Orcia, a small stone hamlet dominated by a mighty fortress.

=> See more Beautiful Villages in Tuscany to visit.

Castiglione d’Orcia

Monticchiello, scenic to a fault

The small town of Montichiello is blessed with an impossibly picturesque historic centre and some sublime views. The landscape here is exactly what you expect from the Val d’Orcia and more. The tower that dominates the town adds a dose of Medieval charm to the romantic narrow stone streets and the flowery windows.

val d'orcia small towns
By AssianirOwn work, CC BY-SA 4.0, Link

The main sight in Montichello is the small parish Church of Santi Leonardo e Cristoforo, that contains frescoes of the Sienese school (14th-15th century) Just outside the town’s walls there’s a great view point from which to take pictures.

The road to Montichiello is the one often seen in photographs of Val d’Orcia with its long snaking road fringed by cypress trees.

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The famous road to Montichiello