Audio Guide: Siena Old Town Walking Tour (Self Guided), Siena

Italian poet Dante Alighieri mentions Siena several times in the Divine Comedy, often referring to the city's famous vanity and extravagant lifestyle during its medieval prosperity. Was he right? A walk through Siena's Old Town may offer a clue.

Siena is one of Italy's best-preserved medieval cities, perched on three hills in the heart of Tuscany. The origin of Siena's name is uncertain. The Latin name Saena Julia appeared during the Roman period, when the settlement became a military colony under Emperor Augustus. It might also be linked to Senius and Aschius, the legendary sons of Remus, who supposedly fled Rome after their father's death and founded the city. According to this legend, Senius rode a white horse and Aschius a black one, inspiring Siena's famous Balzana, the city's black-and-white coat of arms.

Long before the Romans, the surrounding region was inhabited by the Etruscans, but Siena remained relatively small until the early Middle Ages. Its fortunes changed because of its strategic position along the great pilgrimage route connecting northern Europe with Rome, bringing wealth and a steady flow of travelers to the city.

Between the 12th and 14th centuries, the independent Republic of Siena reached its golden age. The city became a rival of nearby Florence, competing in trade, banking, politics, and artistic patronage. During this period, Siena commissioned many of its greatest monuments, including the magnificent Campo Square, the Public Palace, and the spectacular cathedral.

Siena's prosperity suffered a devastating blow in 1348 when the Black Death killed perhaps half of its population, abruptly ending many ambitious building projects, including plans to create the largest cathedral in Europe. Political decline followed, and after prolonged conflicts with Florence, Siena was conquered in 1555.

Unlike many Italian cities, Siena experienced relatively little industrial expansion, allowing its medieval fabric to remain remarkably intact. Today, visitors can wander through narrow brick streets, admire Gothic palaces and churches, and experience traditions that have endured for centuries. Chief among these is the Siena Palio, the thrilling bareback horse race held twice each summer in Campo Square.

Walking through Siena's historic center feels like stepping into the Middle Ages. Narrow brick lanes open onto the magnificent Campo Square, where the elegant Public Palace and soaring Mangia Tower dominate one of Europe's most beautiful squares. A short uphill stroll leads to the black-and-white marble Siena Cathedral, whose richly decorated interior, nearby Piccolomini Library, and surrounding streets showcase the city's extraordinary artistic and architectural heritage.

As you walk through Siena, look around and decide for yourself whether you are seeing the vanity of a medieval republic—or the confidence of a city that knew it had created something truly remarkable.