The Best Things to Do in Pienza, Italy  

A tiny white-stone chapel surrounded by cypress trees, the Chapel of the Madonna di Vitaleta makes an excellent photo opportunity
A tiny white-stone chapel surrounded by cypress trees, the Chapel of the Madonna di Vitaleta makes an excellent photo opportunity | © Henk Meijer / Alamy Stock Photo
Matt Charlton

The largest town in the Val d’Orcia, pious Pienza owes much of its historic architecture, Renaissance art and religious buildings to its benefactor, Pope Pius II. But there’s much more to explore than its Catholic heritage – including some banging food and a famous filming location.

Pope Pius II was born in the village that formerly stood here, and had the vision of creating an ideal city based on the humanist values of the 15th century. It has, of course, changed quite a lot since then, but with its Renaissance architecture, Unesco endorsement, stunning views, romantic alleyways and – most importantly – cheese, it’s easy to see why this is many Italians’ favourite place in Italy.

1. Visit Pienza Cathedral

Cathedral, Church

PIENZA, ITALY - MARCH 4, 2019:The Cathedral of Santa Maria Assunta in Pienza
© Michelangelo Oprandi / Alamy Stock Photo

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.

2. Peruse the Museo Diocesano


Niccolo di Segna, Madonna in trono tra s. Giovanni Battista e s. Giovanni Evangelista, Museo Diocesano di Pienza
© ART Collection / Alamy Stock Photo

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.

3. Walk to the Porta al Ciglio

Architectural Landmark

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.

4. Play pope at Palazzo Piccolomini

Architectural Landmark

Palazzo Piccolomini, inner courtyard, Pienza, province of Siena, Tuscany, Italy, Europe
© Raimund Kutter / imageBROKER / Alamy Stock Photo

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.

5. Buy foodie souvenirs at La Taverna del Pecorino

Deli, Italian

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.

6. Watch an artist at work at Artemisia Art Gallery

Art Gallery

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.

7. Entertain yourself at the 'Gladiator' cypresses

Bed and Breakfast, Farm

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.

8. Have a quiet moment at Chapel Vitaleta


The Cappella della Madonna di Vitaleta, in the heart of the Tuscany, near Pienza in de Val dOrcia valley
© Henk Meijer / Alamy Stock Photo

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.

Looking for somewhere to stay? Book into one of the best hotels in Pienza with Culture Trip. While in the province of Siena, pay a visit to the eponymous capital; here are all the top reasons to visit, including the best restaurants. Don’t miss the must-visit attractions in Tuscany, and if you’re planning an overnight trip to Pisa, we know just the places to stay.

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