Siena is a distinctive-looking destination, with brown-clay roofing and twisting medieval streets. The Tuscan city forms the lower boundary of the famed viticulture region of Chianti Classico. And unlike Florence, its northern-lying neighbour, Siena’s architecture is muted in color, rather than flaming orange. Quietly understated, it attracts a fraction of Florence’s crowds while secretly pioneering an equally impressive character.
A mere glance at Siena Cathedral treats travelers to dramatic Romanesque-Gothic architecture, and there’s even a fort belonging to the Medici (whose rule spread far further than Firenze). The fan-shaped Piazza del Campo erupts into equestrian chaos each summer, as saddleless riders stampede through Siena on horseback. Rumored to be founded by Senius, the son of Remus, one of the twins who founded Rome, Siena has quite the cultural allure.
Not quite a believer? These are the best things to do in Siena, Italy. Here’s what makes the alternative Tuscan city break a prime choice for discerning travelers.
1. Duomo di Siena
Cost: €
To judge an Italian city? Take a look at its cathedral. Duomo di Siena is a landmark of both prestige and beauty; dating back to the 12th century, the facade is adorned with black and white marbled stripes. The exterior is pale at first glance, with ornate carvings and patterns that achieve a real maximalist edge. Architecturally, the cathedral straddles Romanesque and Gothic styles — don’t forget to look up, the striped tower is a fascinatingly unique touch.
Duomo di Siena is just a few minutes on foot from the iconic Piazza del Campo. Standing outside, it’s completely free to admire. Those intrigued by the beauty behind closed doors might be interested in a paid, upgraded experience.
As of 2025, tickets start from €7. Stepping inside, the attention to detail somehow quadruples; Piccolomini Library is the real highlight. Again, the secret is casting your gaze upwards, and the ceiling is adorned with Pinturicchio frescoes and paintings in a whole kaleidoscope of colors. Appreciate the religious art, and lap up the atmosphere as light streams through stained glass window depictions of The Last Supper and The Apostles.
2. Siena National Gallery
Cost: €
The illustriousness of Sienese culture is no secret. One of the greatest Tuscan traversities is that Florence is coined as the cradle of the Renaissance, yet its neighboring city of Siena was equally influential before the tragedy of the 1350 plague. Any art enthusiast will recognize the names of Duccio and Pietro; the stifled potential of Siena’s art scene remains one of the greatest losses of Italian history.
The Siena National Gallery (aka La Pinacoteca Nazionale di Siena) is a time capsule. The gallery evidences the city’s artistic greatness, with walls lined with vast collections of Sienese artwork, from medieval to Renaissance pieces. At just €6, travelers can safely squeeze the Siena National Gallery into their itineraries. It’s far more than artwork, but a reminder of Siena’s role in the Renaissance and the long-lasting impact of the plague. Download the audio guide or ask staff members for additional information.
3. Wine Tasting Tour into Chianti
Cost: €€
No matter how long you decide to stay in Tuscany, wine-tasting should be a priority. Viticulture is at the pulse of the region. Ask anyone about Tuscany, and they’ll mention its wine: the two have become synonymous.
Don’t be fooled by Siena’s cityscape; it sits on the cusp of a world-renowned wine region. In fact, it’s the perfect base to venture into Chianti, the section of countryside that divides the 100 km between Siena and Florence. Famed for dry and earthy reds, a guided experience through Chianti is an ideal day trip from Siena. Organizing a day amongst the vines is easy; book activities through third-party operators like Viator or GetYourGuide. Tours start from as little as €100.
4. Cooking Class
Cost: €€
Think you know Italian cuisine? Think again. Sienese cuisine dances to the beat of its own drum, leaning on traditional recipes and city-specific cultural practices. Siena’s identity has been carefully curated over centuries, and that goes for its food as well. Why not learn how to cook in Siena?
Tuscany villas often provide self-catered kitchens, so it’s often possible to hire a chef to come and teach you. Alternatively, book a cooking class through third-party sites like Viator or GetYourGuide, then cook up a storm behind closed doors. There’s no prettier place to practice.
Naturally, many visitors want to master the Italian classics, like pasta and pizza. However, some specific dishes to watch out for include:
- Ribollita: A vegetable-based soup commonly eaten amongst the lower classes in Siena.
- Panforte di Siena: A traditional cake made from honey, nuts, and sugar.
- Cinta Senese: Meat from a distinctive-looking pig with a white stripe raised in Siena.
- Fettunta: A bruschetta (toast-based) made from Tuscan pane sciocco, garlic, and copious oil.
- Ossobuco alla Senese: Braised veal shank with a tomato and white wine sauce.
5. Palio di Siena
Cost: €€€
If someone mentions Siena, Tuscany? Palio di Siena won’t be far behind. This iconic horse race is roughly as famous as the city’s viticulture-heavy surroundings. Envision Siena, and connotations of wine glasses and horse races pop up almost immediately.
The spectacle occurs twice a year: once in July and again in August. Hurtling around the Piazza del Campo in medieval-style colored outfits, it’s clearly a cultural affair. The excitement attracts as many as 40,000 spectators on the big day, and the cherry on top is that the riders aren’t allowed saddles. Galloping flat-out around the city’s most famed square, it’s a question of nerve, grit, and precarious balance — onlookers marvel at the riders’ ability to somehow “stay put” at speed.
The race isn’t as simple as it might seem, though. Siena is split into 17 contrades, communities tied to specific areas of the city, with links that date back centuries. Each contrade is represented by a color and symbol, and in the Palio de Siena races, 10 of the contrades race at a time. The prize? A large silk canvas, which is adorned by a uniquely painted design. The Palio di Siena is far more than a sporting event; the race sits at the fabric of Sienese culture.
Fancy attending? Reserve online tickets in advance through the official Palio di Siena website. Be warned: reservations don’t come cheap. Expect to budget a minimum of €460 for standing tickets, with prices rapidly rising as high as €8,900 for seated VIP experiences.
6. Santa Maria della Scala
Cost: €
Siena is the surprising home of one of Europe’s first hospitals. The exact dates are shaky, but Santa Maria della Scala is believed to date back to the 9th century, when it opened its doors to care for the lower classes. What developed was a remarkable feat of social welfare, offering medical treatment to orphans, pilgrims, and the needy.
Situated opposite Siena Cathedral, Santa Maria della Scala is a stark reminder of the city’s more saddening history. The complex that stands today (right in the thick of Siena’s bustle) dates back to the 12th century, and is now a hospital-turned-museum. From the outside, it might not look like the flashiest building in Siena. Yet its story is fascinating, and on the inside? You’ll be stunned by the beautiful corridors and valuable artifacts on display. Santa Maria della Scala is hidden in plain sight, and a remarkable example of “don’t judge a book by its cover.”
Tickets are a maximum of € 9.00 online (for general concession without reductions). It’s remarkably good value for money, given that tourists can easily spend two hours on its grounds. The museum itself is a slightly eclectic blend of art, social history, and religious artifacts. Expect elaborate frescoes and relics like the Reliquary of the Holy Nail: a gilded silver artifact said to contain a fragment of the nail that crucified Jesus.
Santa Maria della Scala is an intriguing place to visit in Siena. Where else could you find such a jumbled blend of history and culture?
7. Piazza del Campo
Cost: €
Hunting for the heart of Siena? You’ll find it in Piazza del Campo. Some cities have natural beauty as their center point, like a river, or a religious landmark, like a colossal church or cathedral. Yet for Siena? Its heart and soul lie in Piazza del Campo; the medieval brick square symbolizes culture and community. Out of all the things to do in Siena? Walking the Piazza del Campo is one of the top two.
The fan-shaped square dates back to the Middle Ages and is globally renowned (formerly recognized by UNESCO). It was — and to an extent, still is — a meeting point to discuss the future and affairs of Siena. The Palazzo Pubblico was the former government building, and residents would have gathered to debate and discuss controversial events. Understanding its history is key to appreciating this inner-city attraction; consider taking a walking tour to achieve the most from the experience. Alternatively, climb the 87m Torre del Mangia, admiring the view from the teetering summit.
We’ll revisit this in just a second, but it’s worth mentioning the Palio horse race. This event began in 1633, but continues today. It involves horse riders stampeding through Piazza del Campo, precariously balanced on horseback without the security of a saddle. It remains the most famous of the Siena attractions, and a big part of why Piazza del Campo is so internationally acclaimed.
In summary, Piazza del Campo is best experienced by:
- A self-guided walk
- A guided walking tour
- The Torre del Mangia viewpoint
- Attending Palio di Siena
8. Medicea Fort
Cost: €
The Medici Family was hardly a historical wallflower; the majority of travelers will instantly notice the link. Understand that the relationship between Siena and the Medici wasn’t quite as smooth sailing as it was in Florence, though. Siena endured multiple periods of occupation, and the Medicea Fort is an ancient symbol of their rebellion and subjugation.
When visiting Siena, things to do typically entail Sienese culture. Yet the history of the Medicea Fort is overwhelmingly centered around resistance to enemy power. The fort was initially constructed by an invading Spanish army in the 16th century, and while the Sienese soon saw them off, the Medici struck while wounds were raw. By the 1560s, Cosimo I dè’ Medici had rebuilt the Medicea Fort in an attempt to force Siena into submission.
It’s not all sad stories, though. In true Sienese style, the population reclaimed the Medicea Fort when it was demilitarized in the 18th century. And now, in the 21st century, the fort acts as a beautiful viewpoint over Siena and a public space to unwind. It’s also the home of the Siena Jazz Foundation and a top venue for any festivals or concerts.
9. Basilica Cateriniana San Domenico
Cost: Free
Evaluating on the merit of aesthetics alone? The exterior of the Basilica Cateriniana San Domenico might be a building you accidentally overlook. At first glance, it appears a little “boxy,” with angular, rectangular features creating a simplistic exterior. The most exciting external feature is a 14th-century Gothic tower, poised at 51m above street level. Yet inside? The script flips almost immediately.
The Basilica’s interior is adorned with precious art, including sculptures by Michelangelo and Lombardi. Most importantly, it was built to honor St Catherine of Siena: a patron saint within the Catholic Church, and a certified mystic within the city in the 14th century. And that’s where things take a slightly stranger turn…
Relics can often verge on slight goriness, but in the Basilica Cateriniana San Domenico, travelers will find the entire mummified head of St Catherine on full display. The story behind “the head” is fascinating; the saint actually died in Rome, and her body was held against the wishes of Siena, her hometown. As an act of rebellion, Sienese thieves went to steal a finger and her head (placing it in a bag to sneak past Roman guards), and it’s been displayed ever since. Interestingly, St Catherine is now scattered across the country, with body parts in Venice, Rome, and Siena.
If you ever needed a sign that it’s worth digging deeper into certain attractions? Basilica Cateriniana San Domenico certainly provides one. Behind the facade of a simple church, it cradles relics of St Catherine and valuable artwork by the likes of Michelangelo. Entrance is free, although visitors might be tempted by a paid tour for additional insights into its fascinating backstory.
10. Shop for Siena Leather or Ceramics
Cost: €€€
Forget an ultimate Tuscany packing list; leaving enough space for souvenirs is the secret. We’ve already established Siena’s overlooked role within the early days of the Renaissance. With the influence of the Medici during the family’s rule over Siena, there are notable crossovers between Florentian and Sienese culture, particularly in the cities’ relationships with artwork and artisanal handicrafts. In short, Siena is a home for artists and creatives alike. And one of the greatest things to do in Siena, Italy, is to hunt down the city’s finest leather and ceramics.
Ceramics
Ceramics have been carefully produced for centuries, both as statement artwork in domestic settings and as practical solutions for everyday life. In general, Tuscany has a considerable harvest and storage culture, naturally creating opportunities for ceramic vessels. However, stylistically, it also leans on the concepts of motifs, aka images and symbols, that artists utilize throughout their work as hidden meanings. In Siena, this often relates to the city’s culture, creating a fun game for window-shopping tourists.
Ceramic painting is one of Siena’s oldest artisanal traditions, and there are plenty of variations to watch out for. Here are a few of the city’s varieties:
- Italian majolica: A type of ceramic that is delicately decorated, usually using green or brown colors and images of animals or plants.
- Modern ceramics depict Sienese traditions: These are perfect for tourists and depict traditional motifs and scenes, including the Palio race and contrades.
- Arretine ceramics: An ancient style of deep red ceramics that was popular across Tuscany as a whole, including Siena.
So, how do you find these traditional souvenirs? Via di Città has a ceramic workshop that upholds the traditional artisanal process. Alternatively, visit one of the city’s many ceramic stores, like Ceramiche Bianco e Nero, where a father and daughter duo hand paint stunning items.
Leather
Leather-workers have trodden the streets of Siena for centuries. Did you know that many medieval clothes lacked pockets? While early Sienese bags probably didn’t resemble the handbags on display today, they did form important little pouches. High-quality leather goods were central to day-to-day life, and investing in hand-crafted Sienese leather remains a rewarding souvenir to purchase today.
For those seeking high-quality leather goods, it can (ironically) be quite difficult to find products made in Siena, not Florence. Piazza Gramsci has a Wednesday market where bags, clothes, and shoes are often sold. Just be mindful of guaranteeing authenticity; legitimately Italian-made products should come with certification. Casa della Pelle is an excellent alternative. This renowned shop retails only Siena-made products, and with over 50 years of experience, Paolo Infunti sells hand-crafted bags for competitive prices.