Siena is a mysterious and legendary city, full of secrets and curiosities – like the famous Palio – which make it a place unlike any of the other cities in the former Grand Duchy. From the Middle Ages to today, there have been an infinite number of historical events that have played out in the city, in its small rioni, its historic palaces, its artisan workshops and the terraces that overlook the lively landscape below.
The historical centre, almost completely located inside a Limited Traffic Zone, and its continuous ups and downs – thanks to being built on series of hills – make the city ideal for urban hiking: a different way to stumble across hidden beauties, an itinerary that opens you up to new discoveries and to getting lost in the most evocative little streets. We depart from piazza del Duomo, where the city’s splendid cathedral sits, home to works by Bernini and Nicola Pisano: you can’t miss the chance to visit the sacred building and the nearby Opera del Duomo Museum, from where you can climb to the top of the “Facciatone” and admire the city from above.
From the cathedral, continue through piazzetta della Selva and via del Fosso di Sant’Ansano, a place known for its legends, including the one about The Saint, the patron saint of the city, who was able to miraculously escape a martyrdom. Continue on via Ettore Bastianini, from where you can glimpse in all their beauty the medieval defense walls that connected Porta Laterina to Porta San Marco, and beyond these, the cypress trees that characterize the wavy, rural landscape around the city. Next, head down via della Diana, the street dedicated to the mysterious underground river that seemed to run under the medieval city, before arriving at Porta San Marco and its gardens, another place with panoramic views of the city. Moving toward the Fonte delle Monache, you’ll cross a stretch of via delle Sperandie, offering a stunning view of the countryside, and come to the historic fountain, a small and evocative cave preceded by an opening in the hillside that was once used by Sienese monks as a wash house.
After the fountain, turn toward Prato di Sant’Agostino and its church, another treasure chest full of frescoes and high-value works of art, then make a quick jump over to the Orti dei Tolomei, a designated park from where you can see the Valle di Valdimontone. On the left, a white and orange tower rises toward the sky. This is the Torre del Mangia, one of the highest in Italy, a symbol of the territory and an expression of the city’s power. In Siena’s elegant skyline, it’s said that the town hall’s tower was built to be the same height as the cathedral’s bell tower so as to support neither winners nor losers in the power of the Municipality and the church. And it’s at Torre del Mangia that our walk through the city ends, which you can get to via the Arch of San Giuseppe and the descent down via Dupré.
You’ll finally arrive in Piazza del Campo, a place that needs no introduction, the true heart of the city and home every year to the Palio. To best enjoy this splendid medieval scenery, you’ll want to climb the nearly 400 steps to the top of Torre del Mangia, where you can admire from above the spectacle around you, in the reds of the towers and houses and in the greens and yellows of the hills that paint the countryside beyond.