One of the most sensational areas of the Tuscan countryside is the Val d’Orcia, full of carved hills and colors that change with the succession of the seasons. The region borders Umbria and stretches from Siena to Monte Amiata, taking its name from the Orcia river that runs through it. The valley is filled with extraordinary medieval villages, and the landscape is like looking upon a painting–even if you’ve never been, it inspires a very peculiar feeling of déjà vu, since this valley is one of the most photographed, and idealized, places in all of Italy. 

The still-warm and clear days of autumn are my favorites for admiring the colors of the countryside and experiencing the grape and olive harvest season. It’s enough to just hop in a car and explore the region, but here’s a brief overview of some of the can’t miss towns and sights in this sun-drenched region. Whenever you come through, stock up on cheeses, good wine, and cured meats, and be sure to stop and enjoy the sunset.

VILLAGES IN THE VAL D’ORCIA

Pienza is a small architectural jewel of perfect proportions. It caught the eye of Maestro Franco Zeffirelli, who shot some scenes of his 1968 film Romeo e Giulietta (Romeo and Juliet) at Palazzo Piccolomini. The whole town is undeniably romantic, and certain street names reflect this: Via dell’Amore, Via del Bacio, Via della Fortuna (the street of love, the kiss, and good luck, respectively). Pienza is also the home of the Pecorino di Pienza DOP, one of the oldest cheeses in the world, made with sheep’s milk. To taste the many varieties of this typical cheese, try La Taverna del Pecorino and Enoteca Marusco e Maria. 

The picturesque Montepulciano and Montalcino are surrounded by vineyards, and two great wines are produced here: Nobile and Brunello. In addition to sipping an excellent wine, you can admire expansive views over the entire Val D’Orcia. The medieval village of Montepulciano is filled with elegant Renaissance palaces, and Caffè Poliziano boasts a great panoramic terrace. Montalcino is a treasure trove of art, history, and exceptional Tuscan food. Here, the world-famous Brunello wine pairs perfectly with a plate of cinta senese cured meats or with a dish of pici, the handmade pasta typical of the province. 

In San Giovanni d’Asso, a small village perched near Montalcino, you can find the first museum in Italy dedicated to truffles–a must for lovers of the precious tuber.  

Don’t miss the village of Bagno Vignoni, in the municipality of San Quirico d’Orcia, famous for its thermal spring waters. In the center of the main Piazza delle Sorgenti is a large rectangular pool; at night, the vapors of the warm spa waters rise, creating a fairytale-like view in the square. To swim in the free spas, follow the path of the Parco dei Mulini, which, setting off from the town center, will take you to a natural thermal water pool in just a few minutes’ walk.

WHERE TO EAT IN THE VAL D’ORCIA

Dopolavoro la Foce was built in 1939 as a meeting place for the agricultural workers of the homonymous company. Today, it’s an excellent restaurant that specializes in traditional Tuscan dishes with a stunning view. 

For dinner and a view–both wholly reliant on the land–dine at Taverna di Mozart. At the former, you can also take home homemade cheeses, cured meats, and olive oil. At the latter, all the dishes are made using exclusively local ingredients. Try the homemade pici with flour from the Mulino Val d’Orcia, which you can also visit to pick up a variety of organic products and great flour. Or, stop into Caseficio Cugusi for a cheese tasting or to pick up some salty delights. In 1962, Cugusi Raffaele and Maria moved from Sardinia to Tuscany, bringing with them ancient artisanal cheesemaking techniques and establishing this caseficio, with some 1000+ sheep that make some of the best pecorino in the Val d’Orcia.

Fonte alla Vena offers traditional and seasonal cooking of the area, with particular attention to rediscovering cucina povera recipes. 

Right outside Montepulciano, N.3 Cucina di Verdure is part of Fattoria San Martino, and might very well be the dream of every vegetarian or vegan. The dining room offers beautiful views of the countryside, and the menu is filled with the freshest dishes to pair with organic wines and local beers. Reserve ahead. 

WHERE TO DRINK IN THE VAL D’ORCIA

At Idyllium near Pienza, the cocktails are excellent and perfect for enjoying in the unusual surroundings of the stables of Palazzo Piccolomini, or outdoors in front of an “idyllic” panorama. 

Caffè Poliziano is one of the most famous bars of Italy, and makes a perfect stop for enjoying a drink or a coffee from the terrace with a view. 

Visit Podere Brizio to try the Brunello di Montalcino. You can organize a tour of the estate, starting from the aromatic garden located in front of the pergola of the Foresteria. On clear days, from some windows, you can even see the sea.

WHAT TO DO IN THE VAL D’ORCIA

Bagni San Filippo – An unmissable stop dedicated to wellness. The water rises from the depths of the earth with powerful force, forming concretions of rare beauty.

Puscina Flowers – These botanical gardens are an essential experience for flower lovers. A floral adventure immersed in colors and scents and surrounded by the beauty of the Sienese countryside.

Chapel of the Madonna di Vitaleta – This UNESCO chapel of late Renaissance origin has a single nave and a starry cross vault on the light blue ceiling. 

Teatro Povero di Monticchiello – A social and cultural project born in the 1960s that puts on local theater productions. 

Lucciola Bella Nature Reserve – A beautiful nature reserve with Crete Senesi, which owes its name and the gray-blue color of the soil to the clay, beautiful to drive through. 

Abbazia di Sant’Antimo (Montalcino) – An ancient abbey inhabited over the centuries by Benedictine monks and founded in the 12th century church, considered one of the masterpieces of medieval architecture.  

WHERE TO SLEEP IN THE VAL D’ORCIA

Villa San Sanino, a beautifully renovated 1700s farmhouse in Torrita di Siena, is a family-owned estate with four independent suites, each blending Tuscan farmhouse charm with modern amenities. Laura and Ubaldo transformed the farmhouse into a luxurious retreat, and you really will feel like you’re staying at their dreamhouse. The idyllic setting includes a saltwater pool, scenic views, and a variety of activities, plus a seasonal, onsite, private restaurant.

Locanda del Loggiato is a house dating from the 14th century in the center of Bagno Vignoni. Here, you’ll experience authentic Tuscan hospitality. Barbara and Sabrina, with their enthusiastic smiles and love for their land, will welcome you and guide you to discover the most beautiful places to visit. The b&b is furnished in typical Tuscan style, with terracotta floors and exposed beams. The bedrooms are a dream decorated with four-poster beds, warm and inviting tones, antique and vintage furnishings. There are no televisions (by design), but instead radios to delight guests with music. The common area is a large living room with sofas, a beautiful piano, and a fireplace, which is ideal during the winter to warm up and relax. 

Still under the same ownership, Villa Pienza is an elegant Tuscan farmhouse nestled in the heart of the Val d’Orcia, 10 minutes by car from town. All the rooms are cared for down to the smallest detail. From the windows, you can enjoy incredible views of the countryside. Aromatic herbs and wild flowers grow all along the property and in their garden, and the large swimming pool can be heated on request to enjoy a warm swim even on cool autumn days. A spacious porch furnished with a large table is the perfect place for aperitivo.

Locanda in Tuscany is a family-run inn with a magical atmosphere. Claudia, the owner, is personally responsible for the interiors and her exquisite taste is clear to see. For the most part, the furnishings are recovered and reused materials, carefully sought out and lovingly returned to life: old windows become frames for the mirrors, doors are converted to headboards for the beds, theater curtains are used to embellish huge shower spaces. Everything is designed with the care and relaxation of guests in mind. Prior to arrival, you can even choose between cotton or linen sheets. From the windows and the swimming pool you will enjoy a 360° view over the Sienese countryside, deliberately clear of garden furniture and parasols in order to leave the view of the landscape unspoiled.