​Let's continue our journey to discover the treasures of Tuscany, especially its many medieval villages and cities of art. Among them, Pienza deserves a special mention — a Renaissance jewel rising above the gentle hills of the Val d'Orcia, born from the humanistic vision of Pope Pio II. This Tuscan village, recognized as a UNESCO World Heritage Site, enchants visitors with its perfect harmony between architecture and landscape. In this short guide, we'll explore what to see in and around Pienza, for those who wish to include this charming town as a stop on a tour through a region that has so much to offer.

Where is Pienza located? 

We are in one of the most beautiful areas of southern Tuscany: the Val d'Orcia. Pienza, in particular, is located on the top of a hill overlooking this valley, 53 km southeast of Siena, offering spectacular views from various scenic spots around the town. It is easily accessible by car via the provincial road 146, which connects Montepulciano to San Quirico d'Orcia, offering breathtaking landscapes along the way.

Why is Pienza a UNESCO World Heritage Site? 

Before discovering what Pienza has to offer, it's important to understand why this village is so valuable that its historic center was added to the UNESCO World Heritage list in 1966. Designed by Bernardo Rossellino, a follower of the great architect Leon Battista Alberti, at the request of Pope Pio II, it represents the first concrete application of the humanistic-Renaissance concept of urban planning, understood as a harmony between urban spaces and the landscape. The birthplace of the Pope was completely renovated, becoming an example of human-scale urban planning, with the grandeur of Piazza Pio II at its center, around which the most representative buildings are arranged, which we will explore shortly. This model of the "ideal city" played a key role in subsequent urban development, influencing the design of cities not only in Italy but also internationally.

What to see in Pienza: history, nature, and flavors 

Pienza is unique in its kind, and it still preserves its original unity. Walking through its streets, it's easy to notice how every corner tells a story. Among the best places to visit in Tuscany in​ spring, this village can be explored in half a day. Let's take a closer look at what to see!

Piazza Pio II 

The beating heart of the town, Piazza Pio II is a perfect example of Renaissance urban planning. Its trapezoidal shape, with a herringbone brick pavement, is surrounded by historic buildings, including the Cathedral, Palazzo Piccolomini, and the Town Hall. On one side of the square, at the corner of Corso Rossellino and Palazzo Piccolomini, the hexagonal well known as the "Well of the Dogs" adds a touch of elegance to the ensemble.

Cathedral of Santa Maria Assunta 

Commissioned by Pope Pio II, the Cathedral of Pienza features a travertine façade that gracefully reflects the light. This religious building combines the Renaissance principles so dear to Leon Battista Alberti with Gothic influences, visible in the sloping roof, the central rose window, and the pointed windows. On the outside, the coat of arms of Pio II Piccolomini stands out, while the interior, inspired by the "hall churches" of Northern Europe, is divided into three equally high naves, reflecting the Pope's admiration for this architectural style, which he discovered during his travels.

Palazzo Piccolomini 

The Piccolomini Palace, once the summer residence of Pope Pio II, is a masterpiece of the Renaissance. The interiors house period furniture and a historic library, but the true gem of the palace is its Renaissance-style hanging garden. This small terraced area dominates the entire Val d'Orcia, offering a stunning view of the valley's beauty from the three arches that open onto the ivy-covered back wall, which surrounds this enchanting place on three sides.

Palazzo Borgia – Diocesan Museum 

Adjacent to the Cathedral, the Borgia Palace houses the Diocesan Museum, which collects sacred works of art, including 14th-century panels such as the Madonna con Bambino by Pietro Lorenzetti, known as the Madonna of Monticchiello. For art and history enthusiasts, a visit to this place is a must, as it showcases the cultural and religious richness of the region.

Piazza di Spagna  

Just a short walk from Piazza Pio II, there is another gem: Piazza di Spagna, a more intimate and secluded space that offers a different perspective on village life. While the main square was the center of political and economic power in Pienza, Piazza di Spagna was the economic heart of the town: it was once known as the "piazza delle erbe" (herb square) because this was where the town market took place. This square preserves an authentic atmosphere, with picturesque views and architectural details that tell the story of the city.

San Francesco Church 

Not far from Piazza di Spagna, we find the Church of San Francesco, which is worth a visit for its simple and austere charm. Dating back to the 13th century, this Franciscan church is one of the oldest in the city, and inside it houses precious 14th-century frescoes from the Sienese school, depicting scenes from the saint's life. The spirituality that can be felt within, combined with the beauty of the frescoes and the silence that envelops the space, offers a moment of reflection and quiet in an artistically significant setting.

Panoramic Walk of Pienza 

As mentioned, Pienza is located at the top of a hill, so a panoramic walk along the ancient city walls is a must. By taking the Via del Casello, you can reach several observation points that offer unforgettable views of the Tuscan countryside, perfect for photography enthusiasts.

What to eat in Pienza 

Like other villages in Tuscany, Pienza's gastronomic tradition is closely tied to its territory, offering a cuisine that is simple, genuine, and rich in flavor. You may be familiar with the renowned Pecorino di Pienza, made from sheep's milk and aged in tuff caves, famous for its strong flavor and various aging stages. Served with honey or jams, it makes a perfect appetizer. 

Among the first courses, you can't miss pici all'aglione (thick hand-rolled pasta with a garlic sauce) or pici al ragù di Chianina (pasta with Chianina beef ragù) and bean soup. As for the main courses, standout dishes include Cinta senese or Chianina, local meat specialties that are true delicacies of this region.

What to see around Pienza 

The surroundings of Pienza are rich in charming villages, breathtaking landscapes, and places that tell the history and beauty of the Val d'Orcia. For those seeking a spiritual tour, a stop at the Pieve dei Santi Vito e Modesto in Corsignano is a must. Located less than a kilometer from Pienza, this ancient Romanesque church, believed to date back to the 12th century, is nestled in the peaceful countryside, exuding a rustic charm.

Another unmissable stop is the Chapel of Madonna di Vitaleta, located between Pienza and San Quirico d'Orcia. It is one of the most photographed places in Tuscany, thanks to its iconic frame of cypress trees. Just a few kilometers away, the medieval village of San Quirico d'Orcia invites exploration of its Collegiata dei Santi Quirico e Giulitta, the Horti Leonini, and the ancient city walls. Not far from there is Monticchiello, a tiny fortified village that has preserved its medieval walls, the Cassero Tower, and the Church of Saints Leonardo and Cristoforo, offering an authentic dive into the Middle Ages. 

Also not to be missed is Bagno Vignoni, a unique village where the main square is occupied by a large thermal pool, perfect for those who wish to relax in an atmosphere suspended in time. Finally, a visit to Castiglione d'Orcia and its Rocca di Tentennano offers spectacular views of the Val d'Orcia, allowing visitors to admire the entire valley from above.

Sleeping in a farmhouse in Pienza: the solutions of Tenute del Cerro 

As you've understood, Pienza is just the first stop in discovering a series of treasures that dot the Val d'Orcia. For those who want to immerse themselves in the magic of this place, Tenute del Cerro offers a stay that combines elegance and comfort, while also enriching the travel experience with unique activities, such as tastings, vineyard tours, and visits to the cellars, to discover the flavors and traditions of the region. 

La Poderina, located in Montalcino in the Castelnuovo dell'Abate area and surrounded by the greenery of the Tuscan hills, is the perfect place to relax, with spacious outdoor areas and a view that seems to have come straight out of a painting. Guests are welcomed by two cozy 50 sqm apartments, equipped with every comfort to ensure an unforgettable stay, along with the opportunity to discover the territory where one of the most famous Italian wines in the world, Brunello di Montalcino, is produced. 

Similarly, Fattoria del Cerro, located in Acquaviva, welcomes its guests in an elegant atmosphere, with accommodations carefully designed to the finest detail and the opportunity to explore the vineyards and local flavors. The Relais of Villa Grazianella offers 11 exclusive rooms and a restaurant – L'Antica Chiusina – where Chef Stefano Azzi masterfully reinterprets Tuscan cuisine. Guests can choose from various tasting experiences to learn about the history of the Estate, where another great Italian wine, the prestigious Nobile di Montepulciano, is produced. 

Both properties boast a strategic location for exploring the beauty of Pienza and its surroundings, while also providing an opportunity to take a break from your journey. Fattoria del Cerro, for example, offers the comfort of a panoramic pool to refresh and rejuvenate in the midst of nature after a day of hiking and discovering the Val d'Orcia. 

Have you already booked your weekend in Pienza?