A Historical Walk in Siena, Italy

After an encounter with the dreadful heat wave in Rome last week, my historical walk in Siena, Italy started with a smile complete with positive thoughts. With plenty of things to do in Siena, I planned a self-guided tour well advance. This little medieval town is all about discovering new streets, each opens to buildings adorned with red bricks – these properties were built in 1300s that are now some of the must see attractions in Siena.

While planning my Italy trip, I spent hours in research to understand the Italian culture. What is so unique about it? Is Italy anything like how it’s portrayed in the movies? I watched Letters from Juliet, and Under the Tuscan City almost 15 times (an exaggerated figure) and the little villages fascinated me.


From exploring the Tuscan rolling hills to sampling cheese and chicken washed down by few glasses of Chianti wine with my table overlooking an open farm on a cloudy day to being photographed amid fields of tall wheat plants – I was already dreaming of these on my flight from India to Italy. Well, Italy wasn’t the only thing I was excited about. You see, the flight had a 6 hour stopover in Paris. So I was also contemplating on the perfect sandals to wear just before my land in Paris, best cafe to grab a baguette, should I go inside The Louvre – thoughts were rushing in no particular order and sometimes even repetitive. Let’s talk more about it later.


Siena’s crowning glory was its unparalleled history – especially Piazza del Campo, where the horse race takes place twice every year (July & August). 

The one and half hour train journey from Florence to Siena was gorgeous, the Tuscan landscape was sitting right there on either side of the road snaking up the hill to the medieval cityscape of Siena. Here’s a detailed guide on planning your historical walk in Siena:

Places to See in Siena

Expecting heaps of walking, I treated myself with a cup of coffee and a tonno (Tuna) sandwich from a cafe outside the train station. The genuinely kind lady from the cafe guided me to Piazza Del Campo with her hand gesture due to lack of English skills. I interacted back at her with a similar gesture due to lack of Italian skills (clearly).

What I liked the most in Siena were its direction signs – even a person with poor sense of direction wouldn’t get lost. After walking for less than 10 minutes down a narrow road, I reached the Piazza Del Campo – the main attraction in Siena.


The complex is a shell shaped town with buildings in an oval shape overlooking a vast ground which is slightly built higher than the rest. The ground, cemented in a theatrical manner, serves as a seating for the audience who visit the Campo to watch the Palio. The race, held in honour of Virgin Mary, takes its laps around the audience in Piazza Del Campo ground.


Rumour has it, the ground gets so insanely crowded during the Palio that the true amusement of watching it may be lost or perhaps the event may not be that welcoming to some visitors because of the noise. So I was glad I had a visual glimpse of the much talked about event in Siena.

The city has definitely maintained the impression of Palio all through the walls, you will notice photographs and artworks from the horse race held since centuries. The ground houses the Palazzo Communale which has the Civic museum and a bell tower called Torre Del Mangia. The tower has a lift that takes you to a terrace that offers a 360 degree view of Tuscany (It was out-of- service the day I visited).


In the foreground of the Communale is the Fonte Gaia (Fountain of Joy) intricately adorned with marbles.


I walked back the same route through the narrow roads towards the Piazza Del Duomo, the only difference here among the rest of the Piazza Del Duomo’s in Italy is the beautiful blue Duomo.

Next to the Duomo is the Baptistry. As much as the Roman-Gothic structure was absolutely gorgeous, I chose to admire it from the outside and move on to seeing the Courtyard of Catherina in Fontebranda.historical_walk_in_siena_italy_courtyard_catherina

Located within a few minutes walk, the courtyard of Podesta is the place where St. Catherina lived. It was turned into a sanctuary after her death in the 1460’s.



Tourists are not allowed inside the courtyard. I strolled around the historical property – my favorite was the long patio with a balcony overlooking beautiful Siena.

Basilica of St. Domenico (Church of San Domenica)

After her death at the age of 33, Catherina was buried in a church in Rome. Her body was laid in Rome, and her head was buried in San Domenica after couple of years since she wanted to be a part of the Domenican religion.



Something I found quite an irony was the insinuation of Mother Teresa Di Calcuta in the entrance of the church. Perhaps, Catherina was considered the Mother Teresa of Siena?

Read: Exploring the Leaning Tower of Pisa



Sightseeing in Siena took me 6 hours in spite of the lavish dillydally. I sat on a bench facing the Basilica for a bit, and since I was not taking the bus, I walked back to the train station (to Florence) through the same lane, while I taste some delicious Gelato on the go. Unlike Rome, I did my study on Siena and its history the previous day I visited the city, so it felt all the more familiar.

Read: Check out travel illustrations on Italy

Lovely Corners in Siena

siena street (1 of 1)siena italy roadside 2 attach1 (1 of 1)



I was convinced as though I knew where I was going by myself, at the same time, I loved the feeling of being lost by myself. It made me realise that sometimes traveling solo isn’t that bad after all.

Planning to visit Amalfi Coast? Read this post.

Specifics on Visiting Siena

Train from Florence to Siena

My base city was Florence from where I did all the trips to major cities like Venice, Rome and Pisa. Since I didn’t have a set itinerary, I opted for open tickets. This means you don’t have to purchase tickets in advance, you can buy them from the train station on the day of your travel.

My train timings were more like 10 a.m (Firenze Santa Maria Novella train station) to 11:40.am (Siena train station) in Trenitalia and Return was 15:18 pm (Siena train station) to 16:50 pm (Firenze SMN). Since most of the tourist sights are in the same area, sightseeing requires only 6-7 hours.

Tip:  If you are taking the open ticket, it has to be validated from a green machine found anywhere in the train station – mainly next to the trains.

Have you been on an historical walking tour in Siena? Would you like to add anymore medieval buildings to this guide? Share your comments below.

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  1. says: Tamar

    Great job on catching the major sights and doing research on them before heading out! I winged it in Siena so I feel like your post explained a lot. Beautiful pics too 🙂

    1. says: Shilpa Balakrishnan

      Tamar, I feel researching is one of the best ways to not feel lost in an unknown city. Plus it helps to know the story/history behind it. I am guessing you visited Siena not too long ago. Glad you liked it:)

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