Want to entrust your wanderings in Italy to serendipity, but need just a bit of structure to give you direction? How about a flexible art itinerary following the Piero della Francesca trail through some of the most beautiful countryside and hill towns in Tuscany and Le Marche...

Italy is so dense with fascinating history, world-class art, and—most importantly—unforgettable food and wine that you can simply meander the country guided by serendipity rather than a minute-by-minute schedule and be gratified by what you stumble across. That said, a rough itinerary dedicated to a specific historical period, individual artist or architect, or food and wine is an excellent way to both lend some structure and context to your wanderings while discovering hidden corners of Italy that probably wouldn’t have made it onto a classic tour of A-list sights.

An Artistic Itinerary

a lightray streaming into a church

Renaissance beauty – by Chad Greiter

One memorable yet informal self-guided tour is the Piero della Francesca trail that winds through some of the loveliest hill towns straddling the border between Tuscany and Le Marche, the area where the Renaissance painter and mathematician lived and worked during the second half of the 15th century. Born in the Tuscan village of San Sepolcro, Piero della Francesca is one of the most admired humanist painters of the 1400s, and more than 500 years after his death, his skill with rational geometric perspective on one hand and emotive plasticity and dramatic use of light and shade on the other are still considered remarkable.

Stock up before you hit the road!

A photo in the style of a still life of food

Still life – by Jose Tebar

This driving itinerary passes through some of Tuscany’s most beautiful countryside, so why not pick up some excellent local cheeses, charcuterie, and other specialties for a picnic on the road? Before you set off, stop at a local winery to select a bottle of wine to wash down your lunch…but don’t overdo it if you will be at the wheel!

Arezzo

the interior of the duome di arezzo

The Duomo di Arezzo

Your artistic ramblings begin in Arezzo at the Church of San Francesco, home to della Francesca’s Legend of the True Cross fresco cycle. Thought to be painted between 1447 and 1466, this series of scenes narrates the legend of the origins of the wood used to construct the cross on which Christ was crucified. The cycle is considered the artist’s finest work and a masterpiece of the early Renaissance, demonstrating both his signature use of geometric symmetry and perspective and skill with colour and light.

Piero della Francesca and the Flemish School

Piero della Francesca completed Legend of the True Cross, his largest work, after having spent a year in Rome, where he had been able to examine works by Flemish painters. Their revolutionary use of shading to create drama struck the Tuscan artist, and he began to incorporate similar elements into his own works.

Take the short walk to Arezzo’s Duomo (Cattedrale di Santi Pietro e Donato); here Piero della Francesca was commissioned to paint the Maddalena immediately after completing Legend of the True Cross. This depiction of Mary Magdalene shows the artist’s complete mastery of light and shade, especially noticeable in the saint’s bright glass ampoule containing unguents for Christ’s body and meticulous drapery.

Monterchi

Monterchi is a town on the Piero della Francesca trail

Monterchi – by Franco Vannini

It’s time to head east, following the trail to the tiny town of Monterchi to see Piero della Francesca’s most popular work, La Madonna del Parto. Now housed in a somewhat charmless museum, this fresco originally decorated the tiny country chapel of Santa Maria di Momentana. Why he chose this obscure site to paint such a masterpiece remains a mystery, though some historians speculate the artist was visiting the village to attend his mother’s funeral in 1459. An 18th-century earthquake damaged the church, and the fresco was detached and installed in a nearby cemetery chapel, where it was rediscovered and identified by a visiting art historian in 1889.

In 1992, the fresco was transported to its present museum location for what was supposed to be a temporary move, sparking a dispute between the town and the diocese over the painting’s ownership that continues 25 years later. Despite its convoluted backstory, this mysterious painting has been one of the artists’ most beloved work for more than five centuries.

The Miraculous Madonna del Parto

A photo of the painting La Madonna del Parto by Piero della Francesca

La Madonna del Parto – by Piero della Francesca

Long before the fresco was known to be a Renaissance masterpiece, aspiring mothers-to-be would make pilgrimages to pray to this tender portrait of Mary, great with child and flanked by two angels. Still today, you may come upon a woman quietly supplicating the Virgin for divine assistance on her quest to have children.

San Sepolcro

As you continue east along the Piero della Francesca trail to his hometown of San Sepolcro, you will be going back in time to visit the Polyptych of the Misericordia. The artist’s first important commission, this large altarpiece took seventeen years—roughly 1445 to 1462—to complete and demonstrates the evolution of della Francesca’s skill from the first of the 23 panels depicting saints and scenes from Christ’s life to the last. The most striking panel is the large central Madonna della Misericordia, in which the Madonna spreads her mantle over members of the confraternity who commissioned the work in a gesture that is both protective and perfectly symmetrical.

A photo of the painting La Madonna della Misericordia by Piero della Francesca

La Madonna della Misericordia – by Piero della Francesca

In same Pinacoteca Comunale which houses the Polyptych, you can see della Francesca’s masterful Resurrezione, dating from the early 1460s. Rich with religious and civic symbolism and featuring intricate geometry in its composition, this fresco has been a favourite of English art critics from Austen Henry Layard to Aldous Huxley.

The Saving of San Sepolcro

The subject of Piero della Francesca’s Resurrezione is an allusion to the name of San Sepolcro, so it seems fitting that an essay by Aldous Huxley describing the fresco as the greatest piece of artwork in the world was what inspired British artillery officer Tony Clarke to refrain from shelling the town during the World War II, thus saving the della Francesca’s masterpiece and the town.

Urbino

Photo of the painting the flagellation of christ by Piero della Francesca

The Flagellation of Christ – by Piero della Francesca

You will leave Tuscany now to follow the Piero della Francesca trail into the neighbouring region of Le Marche and the dour hilltop town of Urbino. Here, the stoic Palazzo Ducale is home to the Galleria Nazionale’s permanent collection, including the unassuming yet groundbreaking Flagellation of Christ—a staple in most art history classes due to its stellar use of linear perspective around a single vanishing point and geometric composition—and Madonna.

This final work on the Piero della Francesca trail is also a masterpiece of perspective and composition, tempered by an emotionally evocative facial expression and Flemish-inspired use of light and shade. Thought to have been commissioned for a private chapel, the portrait was moved from the nearby town of Senigallia to Urbino’s Palazzo Ducale during World War I to protect it from damage. Stolen in 1975, the painting was recovered along with the Flagellation in Switzerland the following year and both have been among the gallery’s crown jewels since.

A map of the Piero della Francesca trail

Continue Your Journey

Been inspired and don’t want your journey along the Piero della Francesca trail to end? Other important works by this early Renaissance master can be found in Perugia (Polyptych of Sant’Antonio), Florence (Portraits of the Duke and Duchess of Urbino), and Milan (Montefeltro Altarpiece). Happy trails to you!

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