Among the places that I have visited during this trip, the town of Siena, Italy was one of my favorites because this Tuscan hill-town gave me a sense of being transported back to the Middle Ages. Of the three Italian cities – Siena, Florence and Rome – Siena was the coldest.

Brrrrrr! My phone lens was so blury likely because of the freezing weather. My hands were shaking from the cold as well. Shivers! Siena, Florence’s longtime rival, is a gem of a medieval city.

My mother and I were picked up really early in the morning by our handsome driver, Francesco. Siena is 43 miles away from Florence, about an hour’s drive.

The driver dropped us off at The Basilica of San Domenico, also known as Basilica Cateriniana. He instructed us to wait for our tour guide by the door of the church and to meet him there when our walking tour was over.

I did not find out until I was working on this article that the decaying head of Saint Catherine of Siena, wrapped in a nun’s white habit, was prominently displayed there. I feel bad that I did not do much research before going there. Otherwise, I would have tried to set aside a little more time to explore or I would have booked a later tour. My mother and I were VERY hungry and worried that our walking tour would start soon, so we just lit a couple of candles and offered a few short prayers then we were off searching for a place to have breakfast.

My mom found this charming restaurant, called Il Masgalano, just a few steps away from the church.

Despite it being breakfast, for starters, I ordered Ribollita soup (which is a famous Tuscan soup made with bread, beans and vegetables), followed by lasagna then finished off with cake. I figured I would need the energy provided by all the calories for the walking tour. Hunger sated!

After breakfast, we went back to the church to find our tour guide waiting. We were fortunate enough to take a private tour so we were able to move about at our own pace – to take things as slow as we wanted or to hit the ground running if we cared to.

Our first stop in the introduction to Siena, came in the form of the Consorzio Agrario di Siena (agricultural consortium or cooperative of Siena) which is a grocery store that offers regional foods, deli items, baked goods and specialty products at reasonable prices. Inside the grocery store is a bakery called Menchetti where I bought a zeppola and a pasticciotto.

Though both are Italian pastries, a Pasticciotto has a filling while a Zeppola consists of a deep-fried dough ball.

Banca Monte dei Paschi di Siena is the oldest surviving bank in the world.

We also stopped by a piazza where the neo-classical facade of Saint Christopher church stands out. The church is among the oldest in Siena and, between the twelfth and thirteenth century, was the seat of the great Council of the Republic: the Council of the Bell.

Siena retains a ward-centric culture from medieval times, similar to fiefs or fiefdoms. Each ward (contrada) has its special crest represented by an animal or mascot, and has its own boundary and distinct identity. Ward rivalries are most prevalent during the annual horse race (Palio) at the Piazza del Campo.

The Piazza del Campo, the main town square which is scallop-shaped, is dominated by a 14th-century tower even taller than the one in Florence and is a UNESCO World Heritage Site. It is also home to the Palio, perhaps the most infamous horserace in the world.

The Palio di Siena is a traditional medieval horse race run around the Piazza del Campo, occurring twice each year on July 2 and on August 16. It is attended by large crowds and is widely televised.

One of our pit stops was supposed to be at the Siena Cathedral. From its earliest days, this medieval church in Siena was designated as a Roman Catholic Marian church. Presently, it is dedicated to Santa Maria Assunta.

My mother though, distracted by all the shops, requested a short reprieve from touring so she could shop for a bit and rest her tired feet at the same time. Siena is a hilly town so it was quite tiring for her.
If I were to go back to Italy, I would love to explore Siena more and the surrounding medieval villages.