The Best Things to Do in Pienza, Italy  

Asking if Pienza has a cathedral is like inquiring about the Pope’s religion. Built in 1459, it is one of the most important Renaissance buildings in Italy, commissioned by Pope Pius II and designed by Italian sculptor and architect Bernardo Rossellino. It’s dedicated to the Virgin Mary and was erected on the ruins of the ancient romanesque church of Santa Maria. Containing plenty of paintings and sculptures by Renaissance masters, this gothic wonder is well worth a visit.

There are serious religious undertones everywhere you look in Italy, but in a town founded by a pope you can surely expect twice as much Catholicism. This museum of sacred art, located inside the Bishop’s Palace, contains numerous pieces of jewellery and paintings by the great masters of the Renaissance such as Vecchietta, Luca Signorelli and Fra Bartolomeo della Porta. Overlooking the main square, it’s a great introduction to the city.

One of two main gates of Pienza, and linked to the other, Porta al Prato, by the straight thoroughfare of Corso Rossellino, this is a great scenic spot in the little city. Walking between the two is a great way to get to know Pienza, as you’ll encounter many palaces, religious buildings and remnants of its former glory as the pontiff’s second home.

Just your average papal holiday home, this palace is the first example of Renaissance architecture, so merits a look-see for that reason alone. Built in 1459, its back garden is also the first-ever example of a roof garden in the Renaissance (but with no rooftop bar, sadly). A residential property until 1962, the decor feels frozen in time, and the second floor windows offer beautiful vistas over Val d’Orcia.

If your tastes aren’t particularly religious, this beautiful, family-run deli will give you a respite from all the Catholic surroundings. You’ll find this store a few steps from the cathedral, in a side street off Corso il Rossellino. Step in and choose between gastronomic delicacies including cured meats, wine, truffle, wild boar, sheep’s cheese and olive oil.

Surrounded by Tuscan landscapes that have inspired Italian painters for centuries, it’s no wonder that contemporary artist Isabella Bisa was inspired to fill this space, located right in the centre of Pienza, with artworks. The unique selling point of this particular gallery is that you can stop by to watch Isabella painting one of her creations, before purchasing one to take a little piece of art history home with you.

Spoiler alert: remember the final scene in Gladiator (2000), in which Maximus is dying in the Colosseum and imagines he’s walking back home to his wife and son? This famous scene was filmed in Pienza, between the village and the beautiful family-run Terrapille Farmhouse. You can rent a welcoming and rustic room or apartment there with stunning views of the wheat fields, so run your fingers through the stems and channel your best Russell Crowe impression.

Still not had your fill of religious iconography? Just outside Pienza, beside the village of Vitaleta, lies the charming Chapel of the Madonna di Vitaleta. It used to house a famous statue of the Madonna, but that was moved for easier access for tourists. These days, the tiny, white-stone chapel, surrounded by cypress trees and set against a rolling landscape, makes a great photo opportunity.