Siena Walking Tours: A Must-Do in Tuscany

Walking tours are such an interesting conundrum. Either you hate them or you love them. I know some people who live by them. It’s the first thing they do when they visit a new city. We had a really bad experience in Munich on a free walking tour where an American expat led us (and 30 other people) around the city telling us corny tourist stories that ended up not being true at all. By the end of the three hour tour I vowed to never do another walking tour of a city again.

As the famous saying goes — Never say never right? Fast forward three years and here we are trying out another city tour, but this time it isn’t free and is led by a local who knows the ins and outs of her beautiful city. Costanza from Siena Walking Tours showed us the brilliant side of walking tours and I finally understood why people love city walking tours. Spending a morning strolling around Siena with Costanza was by far the best 3 hours we spent during our 3-day stay in Siena. Read on to learn why this walking tour is a must-do when in Siena! 

Walking with a local

Despite our initial hate for walking tours, after finding out the whole city of Siena was a UNESCO World Heritage Site we knew we wanted to learn all about the history. I started searching for unique walking tours and am so thankful we came across Costanza who runs Siena Walking Tours. 

Costanza has been working as a guide for more than 15 years and is truly one of the loveliest people we came across during our stay in Italy. Unlike most walking tours, we never stood around in front of an iconic spot while listening to some corny tourist story. Instead, the tour felt more like a lovely stroll around the city with a friend. Costanza told us stories of the city contrade, showed us unique (and tourist-free!) corners of the city, and told us about her favorite restaurants throughout the city. 

Siena Contrade

Most cities have “neighborhoods”. These neighborhoods might have different vibes. For example, in Amsterdam the Jordaan district is known to have more local/hipster type places. Whereas in London, Notting Hill is more “upscale”. But if a baby is born with parents from Notting Hill or the Jordaan they aren’t tied to this neighborhood for the rest of your life. In fact, most people could probably care less that their parents are from specific neighborhoods. 

Siena is different. There are 17 different contrade and each is named after a different animal or symbol. Costanza explained that if a baby boy is born in Siena to a father who is a part of the Contrada Del Drago they are born as a “dragon” and will identify with that contrada forever. If the baby was a girl they would be a part of the contrada of their mother. We were fortunate enough to come across a flag with a pink ribbon tied around it which means that a baby girl was just born within that contrada! 

The most fascinating part of the contrada system to me was how connected the people were to their respective contrada. Costanza was very knowledgeable of the history of each contrada and was kind enough to show us around the inner parts of her daugher’s contrada — the Contrada di Valdimontone (the contrada of the ram). Even her daughter’s playground was made of ram figures! The church next to this playground also had a fantastic view of Siena! It’s safe to say by this point I was smitten with the city of Siena. 

Costanza continued the story of the contradas as we strolled around the city highlighting the Palio horse race when we came across a photo of it on the street. Costanza offers a tour specifically on the Palio horse race and I highly recommend embarking on this journey with her. In short, the Palio horse races occur every July and August and each contrada is assigned a horse and jockey to race. There’s a traditional parade and the whole city becomes one big festival for the four days prior to the event.  By the end of Costanza’s explanation and tour of the various sectors of the city that are important during this time, we were convinced we have to come back to see this spectacle. 

Unique corners of Siena

It’s no secret that I love photography and the “local” scene. While strolling around with Costanza we came across a number of areas that were way off the beaten path. We heard Italian women chatting over the clattering of dishwashing, the smells of Italian home cooking wafting through the streets, and finally felt what it must be like to live in this ancient city in the middle of Tuscany. Costanza happily showed us some of her favorite corners of the city without a single tourist in sight. 

The coolest part in my opinion was actually seeing how the city has changed over time. In the picture below you can see all of the different types of stone/brick that were used throughout different periods of history. Costanza pointed out some of the older stones to us and touching them literally felt like putting your hand through time. 

After our tour we were so smitten with the local side of Siena that we spent part of the afternoon looking up real estate to see if it was feasible to retire here one day. Pro tip: It’s probably not the best idea to start dreaming of your retirement in your late 20s with a drink in hand overlooking an Italian piazza after a day exploring the local scene. This activity is bound to bring unbelievable amounts of sadness once you return to real life with work back home. Trust me, I’m an expert on this one. 🙂 On that same note, if you take out the “looking for retirement home” piece having a drink overlooking the piazza is a great idea!

Local Restaurant Favorites

I’ve recently learned that maybe I should have been a food/hiking/travel blogger. Or, maybe I have just visited places recently that have really nice food. I’ve become obsessed with trying new foods and Siena was no different! While we were walking around Costanza pointed out various restaurants that we should try. We tried out one of them — Osteria Il Carroccio — and loved it so much we went back twice! Highly recommended and now I know to trust all of Costanza’s recommendations!

In addition to the restaurants Costanza showed us a really unique spot within the city with a large grassy area, goats, a peacock, and chickens! There is nice lunch restaurant — All’Orto de’Pecci — as well within this area overlooking the grassy spot and one of the best views of Siena! 


Our walk with Costanza was by far our best experience during our 7-day tour through Italy. Despite the fact that we don’t normally enjoy walking tours we absolutely loved our time with Siena Walking tours not only to learn about the history of this beautiful city, but also to find unique local corners of this quite touristy part of Italy. If a city walking tour doesn’t suit your fancy, Costanza also offers many other hiking tours throughout the Tuscan countryside. I know that when we are back in Siena (hopefully for the Palio horse race!) we will be booking a hiking tour with Costanza to see more of Tuscany. 

Special thanks to Costanza from Siena Walking Tours for hosting us on this hike. As always, the gushing and opinions are all my own. We would never write a review for something we would not recommend ourselves!

Happy Trekking!

– Boots not Roots

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