Siena is a magnificent medieval city that’s bursting with things to see and do. From historic buildings that are over 1,000 years old and elegant cathedrals that protect stunning works of art to sprawling piazzas where everyone hangs out and a decadent foodie scene that will definitely leave you wanting seconds, there’s no chance of you being bored here.

Whatever type of vacation you have in mind, you’ll never be stuck for what to do in Siena. From an intricate network of medieval streets and the sensational Duomo to the phenomenal views from the top of the Torre del Mangia and a huge number of world-class museums, you’ll have plenty to do – no matter how long or short your visit is.

With so many things to see and do, you may not know where to begin. To help you out, we’ve put together a list of the absolute best things to do in Siena. Stick to these fun and unique Siena bucket list recommendations, and there’s no doubt you’ll have an amazing time exploring one of the most beautiful parts of Italy!

The 15 Best Things to do in Siena, Italy

1. Climb to the Top of the Torre del Mangia

You’ll find some of the best sights in Siena from the top of the Torre del Mangia. This tall, skinny tower rises up 286 feet into the sky – or 335 feet if you count the lightning rod, too. Construction on this Siena landmark began back in 1338 and it took a staggering 10 years to complete.

Considering how old it is, the tower is in spectacular condition. Located in the Palazzo Pubblico, the tower got its name from its first bell ringer (Giovanni di Balduccio), who had the nickname Mangiaguadagni (meaning “Eater”). He was known by this name because he spent most of his money on food, so the structure is actually called the “Tower of the Eater” in Italian. 

There’s no elevator to whisk you to the top of the tower – just 400 steps that you’ve got to work your way up. The trek is definitely worth it because the views from the top are incredible! 

2. Check Out the Decor of the Siena Cathedral

The Siena Cathedral is, without a doubt, one of the top Siena attractions that you’ve absolutely got to check out. The façade is amazing, made with striking white and black marble that creates a striped appearance on the inside and outside of the building. If you manage to tear your gaze away from the exterior, you’ll be even more impressed by what the cathedral looks like on the inside.

Striped walls, vibrant ceilings, and ornate floor tiles make the Siena Cathedral unique in all the world. Because of the quirky design, the inside of the cathedral can look like a Halloween-inspired haunted house from some angles. Make sure you seek out the frescoes – the detail they display is remarkable. 

Despite how bright and colorful the paintings and decorations are inside the cathedral, the structure is surprisingly old. It dates back to the 13th century and has stood proudly in the center of the Piazza del Duomo as one of the most important landmarks and symbols of the city for hundreds of years.

3. Admire the Fonte Gaia

If you ever find yourself wandering in Piazza del Campo, make sure you stop by the Fonte Gaia. One of the best things to do in Siena, visiting this fountain is at the top of most visitors’ travel bucket lists.

This ancient fountain was completed way back in 1342, and the water that flows through it travels from more than 15 miles away. Decades later, in 1419, Jacopo della Quercia created outstanding sculptures to decorate the fountain.

To help preserve them, many of the original sculptures were removed from the fountain and taken to Santa Maria della Scala in 1858. Some were replaced by imitations created by Tito Sarrocchi, which is what you can see today. If you want to see the originals, you can admire them at the Santa Maria della Scala Museum, also known as the Civic Museum.

“Fonte Gaia” translates into English as “Joy Fountain,” and today, the statues depict scenes from Genesis. Take a look at either side of the fountain, and you’ll spot wolves representing Remus and Romulus spouting water.

4. Wander Around the Orto Botanico dell’Università di Siena

Looking for unique things to do in Siena? You can’t go wrong with the Orto Botanico dell’Università di Siena. This fascinating botanical garden dates back to 1588, when it was originally built as a place for students and professors at the University of Siena to grow medicinal herbs and plants for study purposes.

Today, the beautiful garden is an excellent place to go when you want to get away from the ancient city walls of Siena and get closer to nature. Take a look around the six-acre green space and you’ll discover all kinds of thriving flora.

From tiny fledgling plants kept safe in a huge greenhouse and sweet-smelling citrus trees with colorful fruit to spiky cacti you only usually find in the desert and gorgeous olive trees you’ll struggle not to pick, this botanical garden is a wonderful spot to spend a couple of hours.

5. Sample Pecorino di Pienza

When you need a break from all the Siena sightseeing, stop by a cafe or bar and order some pecorino di Pienza. This delicacy is Siena’s most iconic cheese, even though it’s made in the nearby village of Pienza. If you’re looking for things to do in Siena and fancy a day trip, you can hop on a train and be in the enchanting cobblestone hamlet in just over an hour. 

Alternatively, you can sign up for a guided tour in Pienza and explore a dairy farm where they make the one-of-a-kind cheese. On this tour, you’ll be whisked away to the UNESCO World Heritage Site of Val d’Orcia, where you’ll learn how they make pecorino di Pienza and how to tell it apart from other types of pecorino. At the end of the day, you’ll get to try a few different variations, too!

Pecorino di Pienza is aged for three to five months and is characterized by a subtle, well-rounded taste with a slightly nutty flavor and firm, edible rind. It’s much milder, sweeter, and softer than other types of pecorino cheese and tastes divine when it’s drizzled with honey! 

6. Be Left Speechless by the Biblioteca Piccolomini

The Biblioteca Piccolomini may be small compared to other attractions in the city, but it’s definitely one of the top things to see in Siena. This library is known throughout Italy for its remarkable frescoes and dramatic decor. Every inch of the tiny room is highly detailed, from the walls and the floor to the arches and the ceiling.

Although they’re tricky to distinguish from each other, there are 10 different scenes depicted in the library, all of which relate to the career and life of Pope Pius II. The detail is so intricate and the colors are so bright that you’d swear the frescoes were only painted yesterday. In fact, the library was built between the 13th and 14th centuries. 

As well as the stunning frescoes, the walls are also decorated with ancient manuscripts the Pope collected during his travels. Each of them is hundreds of years old! You’ll find the entrance to the Biblioteca Piccolomini to the left of the Siena Cathedral.

7. Watch a Horse Race That Dates to the 11th Century

Planning on traveling during summer? Then you’re in luck because one of the most exciting Siena activities takes place on July 2nd and August 16th each year. Known as Palio, this thrilling event dates all the way back to the 11th century, when it was first celebrated in honor of the Saint Mary of the Assumption, who is said to protect the city. It’s hard to believe that the iconic festival has been celebrated every year since, but it’s true! 

The highlight of the event is the horse races which take place around the Piazza del Campo. There are 17 riders, each of whom represents one area of the city and wears their own racing uniform. What makes the races so interesting is that none of the riders get to choose their horses – they’re all picked at random. This makes it really difficult to tell who is going to win. 

If you’re super organized, you can buy a ticket and watch the races from one of the balconies of the buildings surrounding the piazza. But these tickets sell out far in advance and can be pretty expensive. A great alternative is to show up early in the morning and find a good spot to stand in the piazza instead. 

8. Explore One of Europe’s First Hospitals

You may not think that a hospital would be on a list of the best things to see in Siena, but just wait until you visit Santa Maria della Scala. Originally one of the first hospitals to open up in Europe, today, Santa Maria della Scala is a fascinating art gallery that’s teeming with dazzling works of art and hidden gems.

The hospital is located along the Via Francigena, a pilgrimage path to Rome, and was built in 898. As demand increased, the hospital was forced to expand again and again until it became the sprawling complex you can see today. It wasn’t until 1995 that the building stopped being a hospital and was transformed into an art gallery.

Santa Maria della Scala is so large that it feels more like a village than a museum. Within the complex, you’ll find religious chapels, an ancient archaeological site, and huge exhibition rooms filled with spectacular artwork. One of the rooms holds a series of frescoes dating back to 1398 that detail the Life of the Virgin Mary.

9. Fly Over Siena in a Hot Air Balloon

If you’ve got a head for heights, one of the coolest things to do in Siena is to get away from the crowds and find out what the city looks like from a bird’s-eye view! Hot air balloons can reach spectacular heights of up to 3,000 feet and reward you with unparalleled views that seem to stretch on forever. At this height, you’re much higher than the winds and can appreciate the sensational panoramas in total peace and tranquility. 

After a safety briefing, you’ll have the chance to help with the aeration of the balloon before hopping into the basket and soaring into the sky. The journey lasts for around an hour, during which you’ll pass over undulating green hills, charming Italian villages, sprawling grape vineyards, and imposing historic castles.

For an experience you’ll be telling everyone about for years to come, you can even sign up for a private balloon tour exclusively for you and your travel buddy. You’ll be treated to a glass of prosecco after – the perfect way to end an incredible experience.

10. Start Your Meal with Pici

Trying new types of pasta is one of the most fun things to do in Siena! A pasta course during an evening meal is standard throughout almost all of Italy, with each region specializing in its own type of pasta. In Siena, most people start their meal with pici.

Pici is a type of rustic spaghetti made only with water, flour, oil, and a tiny bit of salt. It’s slightly thicker than standard spaghetti because the noodles are rolled by hand – not a typical pasta roller. The special Siena pasta is prepared in loads of different ways, with pici all’aglione being one of the most popular. This is pici smothered in a rich tomato sauce enhanced with a special type of garlic that grows between Siena and Arezzo. 

Other popular pici sauces include cacio e pepe, hare ragout, duck ragout, wild boar ragout, and Chianina white ragout, but the pasta can be paired with pretty much any sauce. Trattoria I Barberi serves up some of the most decadent pici in all of Siena. Here it’s covered in a generous serving of delicious wild boar ragout and is so good you’ll definitely want seconds!

11. Stroll along the Walls of the Forte di Santa Barbara

Like many Medieval cities throughout Europe, Siena is surrounded by a giant wall that once protected it from intruders and other unwanted visitors. Today, the ancient wall, known as the Forte di Santa Barbara, is home to one of the must-do things in Siena. 

The Forte di Santa Barbara dates back to 1561, when it was built following orders from Duke Cosimo after the Battle of Marciano against Florence. Today the wall is a popular tourist attraction from where you can check out a number of Siena’s most important sites from a completely new perspective.

Stroll along the wall, and you’ll be able to spot some beautiful parks and gardens, the captivating Torre del Mangia, the eye-catching Duomo, the mesmerizing Basilica of San Domenico, and an ancient amphitheater that looks like it belongs in Athens. As you’d expect from a fortress, the walls are really high and put you in the perfect position to take in the whole city skyline.

12. Visit the Museum of Torture

When you need a break from all the typical things to do in Siena and you’re looking for something a little different, spend a few hours at the Museum of Torture. This eye-opening museum shows the genuine punishments that followed crimes carried out during Medieval times in Italy. Some of the displays are pretty graphic, so make sure you come prepared. 

The museum is divided into different sections, each of which is teeming with replicas of torture devices – paintings, sculptures, and photos of them being used – and descriptive texts filling in the gaps. From the notorious Iron Maiden and Guillotine to the Spiked Punishment Collar and the Heretic’s Fork, there’s a lot to take in here.

Located close to the Piazza del Campo, the museum is open every day for most of the year – except during winter when it’s only open on Saturdays and Sundays. An audio guide is available, but each description is translated into multiple languages (including English), so it’s not really necessary.

13. Gaze at the Statues Inside the Museo dell’Opera Metropolitana

Like Santa Maria della Scala, the Museo dell’Opera Metropolitana is another building that began life as something totally different before it was transformed into an art gallery. Now one of the top things to do in Siena if you want to check out some stunning artwork, this gallery was originally designed to be a cathedral. However, the Black Death that swept over Italy in 1348 quickly put a stop to that and the building was left empty for many years. 

Today the art gallery pays homage to its roots by dedicating its exhibitions to mostly religious artwork. One of the most interesting parts is the section dedicated to Pitano’s sculptures. Pitano was the architect for the magnificent building, and the statues you see in the gallery date back to the 13th century.

At the end of your visit, make sure you take the time to climb the narrow, winding stairs to the terrace at the top of the museum. From up here, your efforts are rewarded with stellar views of Siena that stretch across the whole city.

14. Try More Than 300 Types of Wine

If you’re visiting Siena in November, you’ve got to check out Sangiovese Purosangue. This excellent wine fair is held every year inside the magnificent Medici Fortress and is dedicated to one of the most popular and well-known wines in Italy – Sangiovese.

Sangiovese is known for its striking acidity, with vibrant sour cherry flavors and subtle notes of Mediterranean thyme and oregano. If you know a lot about wine tasting, you may even detect subtle notes of black tea, orange rind, and roasted tomato. If you don’t know anything about wine tasting, you can still have fun trying to taste the different elements! 

Don’t worry if you’re not a big fan of wine – Sangiovese Purosangue is the place to go to discover a wine you’ll fall head over heels in love with. There are more than 30 different types available to sample here. With everything from deep reds and crisp whites to fruity rosés and sparkling proseccos, you’re guaranteed to find at least one variety you like. 

15. End Your Day with Cantucci and Vin Santo

Italian meals are long, drawn-out affairs that last for hours. If you want to dine like a local in Siena, order some cantucci and vin santo at the end of your meal. Similar to biscotti, cantucci is a type of elongated almond cookie that has been baked in Tuscany since almost the beginning of time. No matter when these cookies are eaten, they’re almost always paired with vin santo – a type of super-sweet raisin wine. 

There’s an interesting story behind vin santo. It wasn’t a particularly popular wine until a folklore tale began to spread in Siena. The story goes that a Franciscan friar in the city gave soldiers in need of medical care a few sips of wine and they made a full recovery. It didn’t take long for the story that the wine had medicinal properties and everyone started drinking it. 

Panificio Il Magnifico is an excellent bakery in Siena that makes amazing cantucci. It’s located in the heart of the city and serves up all kinds of homemade Italian desserts and baked goods. Vin Santo is so popular throughout the city that you’ll find it on almost every bar and restaurant menu under “dessert wines.” 

There you have it! The 15 best things to do in Siena. What’s your favorite thing to do in Siena? 

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