Pienza is a delightful small town situated in the heart of Tuscany, just 50 km from Siena. It’s a favored spot for day trips, attracting both locals and tourists. Nestled in the stunning Val d’Orcia, renowned for its rolling hills, Pienza is also home to numerous historical buildings and churches.
Unlike many other Tuscan towns, Pienza does not boast Roman, Etruscan, or Medieval heritage. This is because it wasn’t established in its current form until 1459. The town arose from an ambitious renovation project initiated by Pope Pius II, who envisioned creating an “ideal city” that epitomized Renaissance ideals and aesthetics.
Pope Pius II, originally named Enea Silvio Piccolomini, hailed from Corsignano, a quaint rural village. He aimed to transform his birthplace into a contemporary town.
He enlisted one of the most prominent architects of the time, Bernardo “Rossellino” Gambarelli, who successfully crafted a new city in just five years!
In addition to its architectural wonders, Pienza is renowned worldwide for its pecorino cheese, regarded as one of Tuscany’s finest culinary specialties.
Here is a list of things you can see and do in Pienza:
Disclaimer: This post contains affiliate links. If you click on certain links and subsequently purchase a product, I will receive a small commission.
19 Things to Do in Pienza, Tuscany
Take a Stroll in the Old Town
The historic center of Pienza was designated a UNESCO World Heritage site in 1996, as it exemplifies the ideal Renaissance city. Designed according to Renaissance aesthetics, its squares, streets, and buildings reflect the lifestyle of that era—especially for the noble class! An evening stroll here adds to the town’s charm and elegance.
Visit Pio II Square
Pio II Square is the heart of Pienza, a trapezoidal plaza named after Città della Pieve’s founder, Pope Piccolomini. The square is adorned with beautiful architecture and landmarks, serving as the perfect starting point for exploring the town. Key public buildings can also be found here, including the Cathedral, Piccolomini Palace, Borgia Palace, City Hall, the Presbytery, and Ammannati Palace.
Step Inside the Cathedral
The Cathedral, dedicated to Santa Maria Assunta, was designed under Pope Pius II’s vision, who encouraged the study of German Hellekirchen (hall churches), Gothic cathedrals, and the designs of Leon Battista Alberti, a noted Renaissance architect. Inside, visitors can admire numerous artworks, including an impressive altarpiece.
Explore Piccolomini Palace
This was the summer residence of Pope Pius II, prominently located in Pio II Square. It served as a model for numerous Renaissance palaces throughout Italy, and its façade and layout may seem familiar. The Piccolomini family inhabited the palace until 1962, and it is currently open to visitors.
Throughout summer, various cultural events take place in the palace’s courtyard, with a highlight being the stunning rooftop garden that offers breathtaking views of the surrounding countryside.
Visit the Diocesan Museum
Located within the elegant Borgia Palace, the Diocesan Museum houses an impressive collection of sacred art, featuring several valuable medieval pieces. The museum also showcases the original liturgical vestments gifted to the Cathedral by Pope Pius II during its inauguration in the 15th century.
Pause at the City Hall
The City Hall, featuring beautiful Renaissance-style arcades, showcases the typical architecture of that era, including its towers. Notice how the bell tower is taller than the adjacent brick tower, symbolizing the supremacy of religious authority over political power! You can also tour the boardroom, adorned with exquisite original frescoes. The City Hall still functions as the administrative center of Pienza.
Explore Gonzaga Simonelli Palace
This former residence of the Gonzaga Simonelli family features a roof garden that, while less known than that of Piccolomini Palace, is equally stunning and picturesque.
Enjoy a Romantic Walk in the “Love Alleys”
Couples in Italy adore these charming corners of Pienza, where you’ll find four narrow alleys with enchanting names: Kiss Street, Luck Street, Love Street, and Dark Street. The most popular of these is Kiss Street, which culminates in a panoramic terrace, making it an ideal spot to savor the sunset! Historically, local lovers used to meet here for a bit of privacy.
Visit Pieve di Corsignano
A short distance outside Pienza, you can find the picturesque Pieve di Corsignano, a charming old church dedicated to Saints Vito and Modesto. The church is accessible via a scenic trail from the old town, surrounded by beautiful landscapes and old brick walls. There’s also a large lawn in front of the church, perfect for relaxing outdoors.
Indulge in Pecorino Cheese
No visit to Pienza is complete without tasting its exquisite pecorino cheese! There are several nearby dairies where you can arrange tastings, visit, or shop. Among the most popular dairies are Caseificio Pienza Solp, Fattoria Buca Nuova, and Caseificio di Mario.
Visit the Chapel of the Virgin of Vitaleta
If you’re up for a bike ride (or have access to a car), don’t miss the chance to visit this small chapel surrounded by fields and cypress trees. Legend has it that the chapel was built on the exact spot where a young girl once met the Virgin Mary. It’s a lovely site for a picnic in nature!
Experience a Wine Tour
Tuscany is synonymous with wine, and you shouldn’t skip a guided tour of the finest wineries scattered throughout the countryside! If you want to visit Pienza, consider this tour starting from Florence: Val D’Orcia: Cheese and Wine Tasting Tour from Florence.
Capture Instagram-Worthy Photos
The best spot for capturing beautiful photos of Pienza is along the so-called “panoramic walk” that runs along the ancient walls. The finest viewpoint in town is located on Casello Street, where you can also glimpse Mount Amiata in the distance.
Take a Day Trip to Monticchiello
Situated just 10 km from Pienza, Monticchiello is a beautiful medieval village perched atop a hill and surrounded by ancient walls. It remains relatively undiscovered by tourists, ensuring a tranquil atmosphere. If you visit during the summer, be sure to experience the “Teatro Povero,” a local event in which residents participate in a communal theatrical performance!
Tour the Cloister of the Monastery of San Francesco
This cloister dates back to the 14th century, exemplifying elegant yet simple Franciscan design. Its walls still feature original frescoes depicting the life of Saint Francis, creating a serene atmosphere. Although part of a hotel now, the cloister remains open to visitors!
Find the Filming Locations of “The Gladiator”
If you’re a movie enthusiast, don’t miss checking out two filming locations from “The Gladiator.” The first is an avenue lined with cypress trees near Pieve di Corsignano, while the second is a farmhouse located near San Quirico D’Orcia.
Embark on a Day Trip to Montalcino
Located 23 km from Pienza, Montalcino offers stunning views from its fortress and is famous for producing the renowned Brunello wine!
Consider a Day Trip to Montepulciano
Only 15 km from Pienza, Montepulciano is a must-visit. This historical hill town is famous for its Nobile Montepulciano wine, and it’s an excellent venue for a night out, especially during the summer Jazz and Wine Festival!
Experience the Local Cheese Festival
Known locally as “Festa del Cacio” (with “cacio” meaning “cheese” in the Tuscan dialect), this popular event is celebrated between late August and early September. It features traditional food stalls and characters in costume, with a unique tradition known as the “Cheese Game.”
During the game, a pole is erected in the main square, and participants must lie on the ground and throw a wheel of pecorino cheese as close as possible to the pole! The event includes separate tournaments for adults and young people!
