As you step through the gates of Siena, in the heart of Tuscany, you’re immediately struck by a palpable sense of pride and enduring tradition. Perhaps it’s the vibrant flags displayed outside numerous buildings, fluttering from windows or gracing flower-filled balconies, that first catches your eye.
If you look closely, you might notice how an animal symbol is incorporated everywhere: in door knockers, inlays on the sides of buildings, and street lamps.

You are witnessing a centuries-old tradition. Siena is built on this tradition, so ingrained that everywhere you turn, you see it.
That tradition is called the Palio di Siena, the famous horse race that takes place twice a year. The entire city, along with many famous and non-famous visitors, gathers to watch horses race three laps around the main square.
This trip was in partnership with Sisterhood Travels. All opinions are strictly my own.
I have to confess I had never heard of this race until my trip to Tuscany with Sisterhood Travels this past summer. We had a free day and could choose to stay behind in Montecatini, the village we were in, or spend the day visiting Siena. Initially, I planned to stay behind, but after talking to Liz, our tour leader, and learning a little about Siena, I decided to join in.
Boy, was I glad I did.
Understanding the Palio di Siena
The Palio di Siena is much more than just a competition. It’s a tapestry of passion, history, and unity woven into the heart of Siena. For locals, the Palio is a living tradition, a constant rhythm in the city’s life. Let’s explore what makes this event so special.
Historical Background of the Palio
The Palio di Siena has its origins in the 17th century, specifically in 1633, when the first official race was held in its current format. Before this, the event evolved from medieval jousting and combat sports. Originally, races were held between noble families on horseback or even on buffaloes.
Over the centuries, the Palio has transformed, yet its essence remains unchanged. Each race is a vibrant reminder of Siena’s historical rivalries and alliances. The event occurs twice a year, on July 2 and August 16, each dedicated to the Virgin Mary, reflecting the deep religious roots and continuity of this tradition.
Cultural Importance
For the Sienese people, the Palio is more than just a race—it’s a part of their identity. It represents the fierce pride and rivalry between the city’s 17 districts, known as contrade. Each contrada has its anthem, mascot (an animal or mythical figure), and colors, uniting its community members like family.
The Palio fosters a spirit of togetherness and competition in equal measure. It’s a celebration where emotions run high, and traditions pass down through generations. During the races, barriers of time and space dissolve as Siena erupts into a passionate display of color and the sound of 50,000 spectators cheering their horse to victory.
The festival is actually a four-day event, beginning with the drawing in which the horse that represents each of the ten contrade is selected. Each contrada also selects its jockey. While the jockey is of utmost importance in the horse races we know, that is not true for the Palio.
At 3:00 on the day of the race, the horse is brought into the contrada church to be blessed by the priest. If the horse leaves its own calling card inside, it is a sign of good luck and left there until after the race. There are practice trials, parades, and festivities that take place.

The race itself occurs in the main medieval square, Piazza del Campo. All of Siena attends, along with visitors and the rich and famous, who typically watch from rented apartment windows surrounding the square. There are no rules when it comes to the race. The jockey rides bareback and is issued a whip to use as he sees fit. The horse reigns supreme, and sometimes the jockey will fall off, which doesn’t matter because the horse can still win the race without its jockey. Just watch the August 2019 race.
So what’s the prize?
The coveted Drappellone, a large painted banner, goes on display inside the winning contrada’s museum. Along with that is the bragging rights of the achievement over all the other contrade.
Why is the Palio so important to locals? It’s like a thread that stitches together the fabric of their daily lives, holding together tradition, community, and identity in a changing world. The contrada you are born into is crucial throughout your life.

Experiencing the Atmosphere of the Palio di Siena
But what if you’re visiting when the race isn’t on? No worries! There are plenty of ways to soak up the Palio vibes without being there on race day.
Visit the Contrade
The best way to get a taste of the spirit of the Palio is to wander around and visit a few contrade. You’ll know when you’ve entered a different one. The flags are different, and all those little details change to reflect the symbol of the contrada you are in. Each has its own center with a fountain, church, and museum. When I visited, I spent the most time exploring the Contrada Tartuca (tortoise), stepping inside its museum and church. Some of the churches are closed to the public, but we were lucky enough that this one was setting up for a funeral, and we were invited to take a look inside.


The narrow ancient streets are absolutely stunning. I felt like I was swept up in its rich history. There are shops in each district, and I went on my own secret scavenger hunt, counting how many mascot symbols I saw.
Wander Around Piazza del Campo
Imagine 50,000 race fans gathered inside this square. This is the gathering place and the center of activity in Siena. There are numerous shops and restaurants enclosing the main space. I couldn’t help but stop at Gelateria Il Camerlengo for some creamy gelato (because…hello, Italy), sit at a table outside, and people-watch. Just outside the piazza is Via di Città, which is lined with shops selling souvenirs, women’s clothing, and more.

Tip: I could not visit Siena without bringing back some goodies. I suggest trying some of those delicious cookies Siena is known for called Ricciarelli. They are almond-based cookies made with egg whites, honey, and sugar. So yummy! A container survived the long flight home.
Planning Your Visit to Siena
Visiting Siena is like stepping into a painting filled with vibrant colors and rich history. Even when the Palio isn’t in full swing, you can feel its pulse throughout the city. Let’s make the most of your trip by planning the ideal time to experience authentic Sienese culture, find the coziest places to stay, and navigate the city’s charming streets with ease.
Best Times to Visit
Finding the perfect time to visit Siena is key to a memorable experience. While the Palio occurs twice a year in July and August, immersing yourself in its spirit is possible year-round. I suggest the best times to visit would be spring or fall. The weather is great, and the crowds are manageable. I visited in July, and it was hot. I can only imagine what it’s like in the square during the race in July and August. Winter brings even fewer tourists, and you may be able to take advantage of the local Christmas markets.
Think of Siena as a favorite book. No matter the season, there’s always a new chapter to explore.
Accommodations
Choosing the right place to stay can transform your trip. Siena offers a range of accommodations that suit any taste and budget, many focusing on the Palio’s unique culture. While I didn’t stay in Siena on my visit, like many cities and villages in Tuscany, there are plenty of charming hotels and bed and breakfasts in Siena.
While there, consider taking a guided tour centered on the Palio. You’ll gain insights into the contrade (districts) and learn about their fierce rivalries and traditions. A tour guide can unlock hidden stories and secret spots for you.
Getting Around Siena
Siena is best explored on foot, allowing you to soak in every detail with all five senses. You cannot bring a car inside the city center, which is where I suggest you stay if you are spending more than one day here. The city is compact. To get here, you can take a train or bus.
Whether or not the race is on, Siena invites you to become part of its enduring legacy. Share your experience and let the spirit of the Palio inspire your journey. What will you discover next in this remarkable city?



