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Siena day trip itinerary for art lovers

For most art lovers, spectacular Siena needs no introduction. Sure, it had a historic rivalry with Florence, but don’t pit the two against each other: Siena has plenty of stand-alone power! The Sienese painting school produced masters like Simone Martini, Duccio di Buoninsegna and Ambrogio Lorenzetti; UNESCO named the historic center a World Heritage Site in 1995; even Giorgio Vasari himself called Siena’s cathedral floors ‘the most beautiful and magnificent ever made.’ It’s safe to say Siena’s come a long way since its early days as a modest Etruscan settlement. A work of art in its own right, downtown Siena is packed with must-see artworks and monuments. We’ve shortlisted a few of our favorites for a Siena day trip itinerary.

Siena Cathedral

View of the uncovered floor of Siena Cathedral (press photo)

View of the uncovered floor of Siena Cathedral (press photo)

Construction on Siena’s crown jewel can be traced back to the twelfth century. An extraordinary example of Italian Romanesque-Gothic architecture, Siena’s cathedral has soared in popularity among tourists and contemporary pilgrims, evolving into something of a Tuscan St. Peter’s. The church holds treasures by some of the Western world’s most prominent artists, including a thirteenth century pulpit by Nicola Pisano. Donatello, Jacopo della Quercia, Michelangelo and Bernini are only a small sampling of the other names you’ll find inside. Don’t bypass Pintoricchio’s Piccolomini Library, with a ceiling that rivals the Sistine Chapel in its splendor! Finally, for a limited time each year, the cathedral unveils its marble floors to the public: incredibly intricate, they’re made up of panels that form a tapestry-esque collection of narratives. Try to time your trip for when they’re on full display.

Duccio’s Maestà, the Museo dell’Opera Metropolitana del Duomo 

Maesta Duccio

Duccio’s Maesta (central panel)

Don’t leave the cathedral area without popping in next door to the Museo dell’Opera Metropolitana del Duomo, worth it for Duccio’s glimmering masterpiece alone. This enormous early fourteenth-century altarpiece depicts the Madonna and Child enthroned with angels and saints on its front. In its original position on the cathedral’s high altar, this was the image that faced outward toward the congregation. The four odd figures leaning in toward Mary are the city’s guardian saints, pleading for her favor and for a peaceful Siena. But the story doesn’t stop there: on the reverse side of the altarpiece are over forty small panels, which earned Duccio posthumous recognition for his trailblazing artistic techniques. Read more about how Sienese Renaissance art differs from that of Florence.

Church of San Domenico

Interior of the Basilica of San Domenico in Siena (photo: wikipedia)

Interior of the Basilica of San Domenico in Siena (photo: wikipedia)

San Domenico never ceases to wow travelers, towering over the city and reeling in passersby even from below. This thirteenth century basilica is one of Siena’s most instantly recognizable monuments, despite the fact that its exterior is much less lavish than, say, the cathedral facade. The interior is home to masterworks by Matteo di Giovanni and Francesco di Giorgio Martini. What makes this church particularly memorable, though, is its link to Saint Catherine of Siena. Fascinated by relics? The Cappella di Santa Caterina holds its namesake’s head and finger!

Pinacoteca Nazionale

Stop in at the Pinacoteca Nazionale to get a sense of Siena’s longstanding artistic importance and influence. The extensive collection moves from the Gothic up to Mannerism, and includes all the illustrious names of the Sienese school. Renaissance junkies and Florence lovers should pay particular attention to the fifteenth century pieces, which shed light on why Florence was the artistic frontrunner of the two cities. These Sienese works, while well worth your while, demonstrate those painters’ enduring tendency toward Byzantine and Gothic techniques

Allegory of Good and Bad Government, Palazzo Pubblico


Lorenzetti, scenes from the frescoes of Good and Bad Government

The renowned ‘Room of the Nine’ is only one small fraction of the Palazzo Pubblico, but it deserves its own entry for housing Ambrogio Lorenzetti’s famous (and, in part, foreboding) fresco cycle, The Allegory of Good and Bad Government. Intended as a warning against the widespread corruption and instability in fourteenth century Italian city-states, Siena’s city council commissioned Lorenzetti to produce panels on the effects of stable, virtuous leadership, versus the pandemonium-like consequences of poor government. The three subjects in the series are the Allegory of Good Government, Effects of Good Government on Town and Country, and Effects of Bad Government. On the eastern wall, the Effects of Good Government on Town and Country depicts tranquil city-dwellers and rural residents happily tending to their daily tasks—and though Effects of Bad Government is less well-preserved, its metaphorical mayhem is bound to intrigue you. No matter how long you stare at this politically charged trifecta, you’ll find something new every time you visit.