Strolling Through Siena: A Tale of Old Towns and Modern Contrasts

As legendary fashion editor Diana Vreeland once said, "The eye has to travel," and oh, how true that rings! My travel adventure allowed me to immerse myself in the beauty and charm of Siena, Italy, inspiring me in ways I never expected.

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location: Siena, Italy

date: August 2023


Siena’s historic center maintains a rare equilibrium between contemporary commerce and local life. Kitschy souvenir shops, yes, but just enough. Residents emerge from supermarkets carrying shopping bags with baguettes and celery sticking out on top. In the same supermarkets, sweaty tourists stock up on bottles of cold water and crunchy snacks. Adding to this eclectic mix are typical green Tuscan hills embedded in the heart of the city, a whiff of the breezy romance of the countryside. 

The city of Florence has for centuries been famous for its leather industry. In Siena (which falls under the broader Florentine region), leather goods shops seem to outnumber fast fashion retailers. Yet you often find out that evoking the tradition of Florentine craftsmanship is merely a marketing tactic. The goods may be handmade, but in China instead of locally. 

A typical Sienese morning sees early tourists trailing behind garbage trucks. Garbage collectors jump on and off to pick up neatly tied bags that residents leave at the entrances to their shops and homes. Siena’s old town properties have not (yet) been wholly handed over to rental platforms. It all still feels relaxed, harking back to pre-Covid times. There’s no hostility or frustration aimed at tourists, no graffiti decrying gentrification and overtourism, not an avocado toast in sight. 


The old town is a whirlwind of cars and motorists speeding around pedestrians in short bursts. It’s more chaotic than overwhelming, but it does make me appreciate that my hometown Ljubljana long ago banished motor vehicles from the city center. Whenever I find myself in a particularly beautiful old town, such as Siena or Seville, I miss this feature of Ljubljana. With traffic, ancient streets always feel too narrow.


In Siena, vehicles and other displays of contemporary life (such as air conditioning units) coexist with damaged medieval architecture. It’s a fascinating contrast between profane and sacred. Should old buildings remain dilapidated but sacred in spirit (their sanctity stemming from visible, rich history)? As a tourist and photographer, do I prefer neat exterior plaster facades instead of exposed bricks? Do I prefer renovations to urban decay, thus losing some of the old city’s authenticity? 

Walking around Siena, I thought of old palaces on Budapest’s Andrassy Avenue. Their exteriors may be crumbling, but they still house embassies. In England, drafty and squeaky Victorian houses are revered because of their character. New builds, meeting all the latest standards of comfort, are less desirable. It seems that many of us appreciate a touch of sacred in our profane.


Siena’s main square, the concave Piazza del Campo, hosts the city’s most famous event: the annual Palio di Siena horse race. When I first visited Piazza del Campo some five years ago, my first instinct was to follow in James Bond’s footsteps. With great curiosity, I located the manhole he climbs out of in Quantum of Solace (2008) during the Palio race. The subsequent spectacular chase across Siena’s rooftops was also filmed in situ, but here following in double-oh-seven’s footsteps (that is, jumps) would require a different level of fitness. 

This year, unbeknownst to us, the Palio horse race took place one day before our arrival. When we got there, Piazza del Campo was still covered in a ring of dried mud that horses and crowds had trampled the day earlier. It was 37 degrees Celsius (99 °F). The cafes overlooking the square had stopped using water mist cooling systems, probably to save water. We caught Piazza del Campo at an inopportune moment and missed its usual charm. 


In Europe, the city’s main square has fostered socializing and commerce since the Middle Ages (even earlier, if you count the Roman forum). A recent development that I love revisiting is Milan’s Piazza Gae Aulenti, which opened in 2012. The square is extremely commercial with every kind of shop including a Tesla store, bars, restaurants, and clubs. At the same time, groups of teenagers hang out by the massive fountain, having fun without spending money. The atmosphere is dynamic and zestful. 

Siena’s Piazza del Campo captures a different essence altogether. Unlike Milan’s modern and bustling Piazza Gae Aulenti, Siena’s main square seems frozen in time, preserving the spirit of centuries past. Its shell-like curvature creates a natural amphitheater where historical events, ceremonies, and, of course, the Palio di Siena unfold. The bare dirt was a tangible reminder of Siena’s deep-rooted tradition.

In contrast to the sleek commercialism of Piazza Gae Aulenti, Siena’s main square is a place where past and present coexist. As the day drew to a close, I appreciated the unexpected beauty of catching Piazza del Campo in its raw, post-Palio state. Sometimes it’s the imperfections and the unexpected moments that reveal a destination’s true character.

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