Weekend in Siena: a local itinerary from Friday to Sunday

Spending a weekend in Siena is like diving into the vibrant heart of Tuscany. Every corner tells fascinating stories, from medieval splendor to the lively contrade, allowing us to discover an authentic and genuine city.

During our journey, we’ll explore some of the most iconic attractions, from the picturesque Piazza del Campo, the true soul of Siena where the famous Palio takes place, to the magnificent Duomo, with its stripes of marble shimmering in the sunlight.

Our weekend will not be limited to visiting the most famous sites. We’ll also savor delicious local specialties, such as pici with ragù, panforte, and the fabulous wines of the region. Without forgetting the opportunity to enjoy excursions in the surrounding countryside, from the enchanting hills of the Crete Senesi to the refined wineries of Montalcino.

So here are the 10 things to do in a weekend in Siena: let’s get ready to discover the timeless charm of this city on a journey through history, flavors, and landscapes that leave a mark, for an experience that is truly unforgettable.

Piazza del Campo opens up like a stage, framed by elegant medieval palaces that seem almost like sentinels watching over the city's life. It truly represents the heart of Siena, a place that hosts the most important events in the city with its characteristic shell shape, extraordinary and unique in its kind.

Your weekend in Siena can only begin at this iconic location: a square dating back to the 13th century, which was already a meeting point and place of exchange for the citizens. Over the centuries, it has transformed into a symbol of Sienese identity, uniting cultures and traditions that can still be felt in the air today.

If you arrive in the city on Friday afternoon, head straight to Piazza del Campo and discover its magnificent architecture. At the center stands the majestic Torre del Mangia, which at 102 meters tall provides a sense of grandeur and majesty, as well as a breathtaking view. The Palazzo Pubblico, with its beautiful façade, is a testament to the ancient city institutions and the decisions that have shaped the history of Siena.

Every year, during the summer months, the square transforms into a vibrant arena for the famous Palio di Siena, a historic horse race typical of Italian tradition that takes place in July and August, involving all the city’s contrade (districts).

This race, which has been held since 1644 but has even older origins, represents much more than just a race: it is a manifestation of identity, history and passion that engages the entire community. During these events, Piazza del Campo becomes more than ever a place of great participation, with celebrations, flags, and an electrifying atmosphere.

Speaking of atmosphere, even in the evening Piazza del Campo is a lively and pleasant place, the perfect starting point for a stroll through the picturesque streets surrounding it, in search of a typical restaurant where we can begin to discover the extraordinary Tuscan cuisine.

Let’s dive into the 10 things to do in a weekend in Siena, starting bright and early on Saturday morning. Head back to Piazza del Campo, this time not just to admire its remarkable architecture but to ascend one of its most iconic landmarks: the spectacular Torre del Mangia.

Constructed between 1338 and 1348, this towering structure dominates Piazza del Campo with its impressive 102 meters, making it one of the tallest medieval towers in Italy. Climbing its 400 steps is no small feat, but every ounce of effort is rewarded with breathtaking views of the city and a palpable sense of medieval history in the narrow, evocative stairwells.

During Siena’s golden age, the Torre del Mangia served as a striking emblem of its power and influence. Today, the toll of its bell continues to mark significant moments in the life of the community.

Once we’ve descended the tower, let's continue our exploration by leaving Piazza del Campo behind and heading towards the majestic Piazza del Duomo. In theory, it's enough to walk the few meters down Via dei Pellegrini to reach Piazza San Giovanni and the back of the Cathedral, but our recommendation is to take Via di Città, a gently sloping street that opens up right in front of the building, so that we can admire its full splendor.

The Cathedral of Siena is, in fact, an open-air work of art, with a stunning facade of black and white marble that reflects the elegance and majesty of Italian Gothic style.

The building holds centuries of history and spirituality: one of its most remarkable features is the intricate floor, one of the most beautiful in the world. Additionally, we must not miss the Crypt, a frescoed area discovered only in 1999 after remaining intact and hidden for centuries; the Museum of the Opera della Metropolitana, which houses artworks and sculptures related to the Cathedral and the city's history; and the “Facciatone”, a majestic Gothic facade. 

The Cathedral also hosts the Piccolomini Library, whose frescoed walls tell the stories of Pope Pius II, originally from nearby Pienza.

Given the uniqueness and popularity of the place, it can be wise to book your entry in advance. Visiting the Cathedral is, in fact, an unmissable and highly sought-after experience: it means not only discovering a masterpiece but also feeling the deep connection that ties Siena to its traditions and cultural identity.

Spending a weekend in Siena is a truly captivating experience, especially from a historical and artistic perspective. But every now and then, it’s essential to take a break from sightseeing, sit down at a restaurant table, relax, and savor the extraordinary local cuisine.

After visiting the Duomo, let’s stop at one of the many traditional taverns scattered throughout the old town, the kind of place where time seems to stand still. Here, surrounded by stone walls and vaulted ceilings, with rustic wooden tables and a warm, welcoming atmosphere, you can pause for a few hours to savor the authentic flavors of the region.

Sienese cuisine celebrates simple flavors, embodying a gastronomic heritage passed down through generations, deeply rooted in rural traditions.

Take the pici, for instance—thick, hand-rolled spaghetti that pairs perfectly with meat ragù or more rustic toppings like garlic sauce or breadcrumbs. This dish is a true taste of tradition and flavor, and trying it offers a rich, genuine taste that, with every bite, reveals the soul of the city.

Another highlight among local products is, of course, wine. Siena is located in one of Italy’s most famous wine regions, so why not savor a glass of Brunello di Montalcino or Chianti? These bold, intense reds pair beautifully with Tuscan meats or typical cheeses.

Finally, make sure to leave room for dessert. Siena’s signature sweet is the panforte, a delightful treat made with honey, dried fruit, and spices. Panforte takes you right back to the Middle Ages, with every bite offering a taste of history, recalling the days when it was made in monasteries and served during religious festivals.

In the evening, let’s not limit ourselves to staying in the enchanting Piazza del Campo. Instead, take a stroll through the surrounding streets to discover Siena’s most intimate essence: its contrade.

The streets branching out from the square reveal charming views and lead to the small worlds that define the city. Walking through the ancient alleys, you’ll come across glowing lights from taverns, traditional osterias, flags hanging on walls, and coats of arms that tell stories of rivalry, traditions, and community.

Each of Siena’s 17 contrade is more than just a geographic area; it is a vibrant microcosm with its own identity. The symbols of the Civetta (Owl), Drago (Dragon), Chiocciola (Snail), and Oca (Goose) are more than mere emblems; they are signs of a pride handed down through generations. The residents of these contrade are not just neighbors but members of a large family celebrating their traditions with events, activities, and festivities.

The Palio di Siena, with its vibrant energy and colors filling Piazza del Campo twice a year, is the pinnacle of contrada life. However, the pride and sense of belonging are always palpable, in every corner of the city’s streets.

For this reason, an evening walk through the contrade is not just a way to explore the city but an opportunity to truly connect with its most authentic soul.

During a weekend in Siena, if we have the opportunity to travel independently on the road, we can choose to dedicate half a day to exploring the magnificent territory surrounding the city.

The Crete Senesi are enchanting rolling hills distinguished by their gray-blue color, derived from the clay soil that characterizes them. In spring, they are dressed in intense green, while in autumn, the hues turn golden, offering a magnificent spectacle that changes with the seasons.

Walking the trails of the Crete Senesi means traversing places where nature and silence convey a deep sense of peace and harmony. An excursion here is a sensory journey of discovery through stunning views and postcard-worthy landscapes.

Among the recommended routes is one that starts from Asciano, just 40 minutes by car from Siena, winding through the surrounding hills and passing by panoramic points that offer spectacular views. Following this itinerary, we can explore the typical Tuscan landscape, with gentle hills, vineyards, and small villages waiting to be discovered, each with its unique charm and story to tell.

Let’s conclude our journey through the top 10 things to do during a weekend in Siena with the suggestion of another excursion out of town, particularly suitable during the warmer months: a fascinating half-day tour to Montalcino, a splendid village located about 40 kilometers south of Siena.

After crossing the vineyard-covered hills that define the beautiful Tuscan landscape, we can explore the village's historic center and visit its impressive fortress, a medieval structure offering fantastic views of the surrounding area.

The tour continues at one of the local wineries, where the true tasting experience begins. Awaiting us is a selection of Brunello di Montalcino, one of the most awarded Italian wines worldwide, along with other typical Tuscan products. Together with an expert guide, we’ll discover the secrets of Brunello, from the production process to the unique qualities of this full-bodied, intense red wine.

After the tasting, before returning to Siena, we can immerse ourselves once again in the timeless atmosphere of the village, among the quiet of the hills and the warmth of local hospitality.

This bonus tip is the perfect conclusion for our journey through the 10 things to do in a weekend in Siena, an unmissable chance to savor the history and flavors of Tuscany, and a precious memory to carry with us forever.