You must put the Italian city of Pienza on your bucket list during your next visit to Tuscany. It’s a delightful and beautiful, small, walled town devoid of crowds of tourists. It’s architecture is notable and it has a spectacular view of the Orcia Valley and Mount Amiata, an extinct volcano.

It is also the birthplace of a Pope.

Pienza is also famous for its Pecorino, a sheep’s milk cheese, that has a  unique, complex flavor in this region due to the sheep’s diet of the local wild herbs (so they say.) Pienzanos are also proud of their pici, a thick, hand-rolled spaghetti that is found throughout the province of Siena.

How I stumbled upon Pienza: Each year, I teach a watercolor workshop in Italy through il Chiostro, a company based out of New York which is owned and operated by two Italian-American Italophiles dedicated to creative workshops throughout Italy. My “Watercolor Immersion in Italy” workshops are usually a week of intense painting at one of the many picturesque venues il Chiostro provides with room & board including delicious, locally-inspired meals prepared by a chef. il Chiostro has vans to take our group on daily painting and exploration ventures to nearby towns and villages.

This year we were at San Fedele, a beautifully restored 11th century monastery near Radda in Chianti and not far from the medieval, walled city of Siena. Each day we ventured into a new town or village for a painting excursion. Upon discussing where to take the students on that upcoming day, Michael Ferris, a Program Manager for il Chiostro and our driver that day told me, “It’s a bit of a haul for us but I am sure you will love the town.” Boy, was he right about that. Pienza was a great call.

We drove through the picturesque Crete Senesi (or ‘Sienese clays’) region on our way to Pienza. A beautifully strange, moon-like landscape with the exception of vineyards, the occasional row of cedars and hilltop walled towns, farms, or estates. The large chunks of clayed soil are the result of tilling and during the spring and summer, you will find expansive fields of wheat. The area is a favorite of photographers.

Pienza used to be called Corsignano (ironic as that is also the name of the winery we had a tour of and dinner one night not far from San Fedele; many of us purchased wine and olive oil that was shipped to the US; my order beat me home.)

Well, Corsignano it was until a home boy, Enea Silvio Bartolomeo Piccolomini (1405-1464), a well-known Humanist scholar and philosopher, changed his name to Pope Pius II in 1458 and renamed the town after himself. I read a lot about this and wondered how ‘Pienza’ related to this Pope: I finally read that ‘Pienza’ means ‘city of Pius’. OK, that explains it…

Pope Pius II is known for many things including canonizing Saint Catherine of Siena and trying to convince his good buddy, Vlad III Dracula, to start a war against the Sultan of Turkey. He was admired as a poet and even authored erotic poems, ah yes, but that was before he landed the big job.

Maybe his real legacy is the renaming of the town to Pienza. This coincides with Pius II’s desire to transform his birthplace into an ideal Renaissance center. He hired Florentine architect Bernardo Rossellino (a student of Alberti) to build a Duomo, papal palace, and town hall all of which were miraculously completed in three years.

The architect was caught with his hand in the papal cantucci jar and destined for prison though Pius II forgave him (he was very delighted with his new buildings!) Rossellino’s buildings created the focal point for an ideal Renaissance city combining civic and religious buildings which combined were the first example of Renaissance town planning. As an American, I always find it amazing that here are buildings completed decades before Europeans first visited (note that I didn’t say discovered) the New World.

As we walked into the town, it was refreshing to not see so many tourists. The town is delightfully quaint with restaurants, enotecas, and shops here and there in an atmosphere that makes one feel as though they have stumbled upon something very nice.

I was struck by the dramatic view behind the Duomo which was on the edge of the city walls. I began painting from this vantage point and as I got into the painting, a familiar buzz came up behind me: It was a drone flown by an American couple from McLean, Virginia (no, I don’t think they were CIA). The young man was generous to oblige my request for a shot of me painting from a bird’s eye view.

[Watch my video below to see it.]



After painting, we had an enjoyable lunch in a restaurant and afterwards found a gelateria Michael recommended on our way back to the van. Here was my real culinary find: a gelato flavor called Olio Novo (new olive oil) and as unappetizing as it sounds, it was amazingly delicious and now listed as my favorite flavor.

Pienza is definitely a return visit on my next trip to Tuscany. Perfetto!

Robert Leedy is a Florida artist who paints in the medium of watercolor. Leedy maintains a studio in the CoRK Arts District, a warehouse studio complex in Jacksonville’s Riverside neighborhood. He is a plein air painter with the majority of his work coming from outside of the studio. Leedy participates in many plein air events and teaches watercolor classes and workshops locally and nationally along with an annual workshop to Italy. He also offers private classes and mentoring. His paintings are available for sale and he also accepts commissions. See more of his work at www.robertleedywatercolors.com and sign up for his newsletter to stay informed of upcoming exhibitions, classes, workshops and trips to Italy. 

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