Things to do in Siena

Standing here in Siena’s Piazza del Campo, you can imagine the thundering of hooves and the roaring of the spectators.

The energy must be incredible, thousands of people crammed together in the centre of the square as the horses race around them. Encircled and squashed, there would be nothing to do but shout with the crowd.

Twice a year, this historic square hosts one of the world’s most famous horse races. And the Palio di Siena is no ordinary race!

The outside of the piazza becomes a racetrack and is covered with turf. The inside becomes the main spectator area and thousands of people are squeezed in and then locked into the area just before the race starts.

Ten horses compete. I say ‘horses’ rather than ‘jockeys’ because the rules clearly state it’s the first horse across the line that wins, regardless of whether the rider is still attached.

The race is run bareback and, with some tough corners, the jockey doesn’t always make it to the end.

It’s also a rough race where the riders are allowed to use their whips on the other competitors, so that doesn’t help their chances.

One of the reasons Il Palio is so rough is tradition. The race was first run in 1656. In that day – and still to this day, as a matter of fact – it is a competition between the different districts of Siena.

Much like any football league around the world, the crowd is often just as happy if their archrivals don’t win than if they do themselves. There are apparently even some dirty tactics that go on sometimes, with two or more districts secretly agreeing to gang up on another.

A day in Siena

If you ever get a chance to see the race, it’s one of the best things to do in Siena. But most visitors to this gorgeous Tuscan city will miss it.

Today, as I’m visiting Siena, things are much more sedate. It’s a warm and sunny spring afternoon and the piazza is full of people sitting on the ground, catching some rays, eating a snack or talking with their friends.

The shadow of the tower from the imposing Palazzo Pubblico casts a shadow over the ground and moves like a sundial. The people who end up in its darkness shuffle back into the light… the whole process continues slowly as the shadow marks the passage of the day.

The historic centre of Siena is as beautiful and charming as I’ve come to expect from the old cities in the region, and it’s certainly one of the best places to visit in Tuscany.

A wonderful example of a medieval settlement, it still shows the city’s Gothic appearance, acquired between the 12th and 15th centuries. The whole city was devised as a work of art that blends into the surrounding landscape.

For instance, the Duomo, with a similar Tuscan Gothic style as the one in Florence, is considered one of the finest in the whole country – and the things to see there could take up much of a day in Siena.

The streets of the old city are full of pedestrians (most of whom are tourists, to be fair) and it’s mostly without cars in the historic parts.

Siena is one of those places that is a pleasure to walk around, to peek into the stores selling crafts, stop for a coffee in one of the bars or sit for a while in the squares and watch life go by.

I can only imagine what Siena is like when the Il Palio roadshow comes to town. Chaotic and noisy, I’m sure it’s also a lot of fun.

For now, though, for any normal day, to help you with your visit, let’s have a look at some of the best things to do in Siena.

Palazzo Pubblico

Siena’s Palazzo Pubblico (also called Palazzo Comunale in Italian) is one of the many wonders the Tuscan town offers. It’s a beautiful medieval building that dates back to the 13th century when it used to be the administrative centre of the Governo dei Nove (Government of the Nine) of the Republic of Siena.

With a stone-and-brick façade, the Palazzo Pubblico stands right in the central Piazza del Campo and houses masterpieces from the golden age of Sienese art.

Palazzo Pubblico is an iconic Italian building due to the many frescoes and other art pieces stored inside and the famous Torre del Mangia.

To save time during busy periods, I would suggest buying your ticket online before you go.

Civic Museum

Enter the Palazzo Pubblico to visit the Civic Museum. With opulent rooms full of frescoes and artworks, the Civic Museum is an unmissable stop while in Siena. Among the many things you will see inside the museum, the highlights are the frescoes in the Sala dei Nove (the Hall of Nine), Sala del Mappamondo (the Hall of the Globe), and Sala della Pace.

In the latter room, you can marvel at the world-famous fresco by Ambrogio Lorenzetti called ‘The Allegory of Good and Bad Government’. This fresco is an excellent example of the Sienese school of painting.

Torre del Mangia

Rising from the Palazzo Pubblico is the tall and skinny Torre del Mangia. With a height of 88 meters, the tower’s construction began in 1338 and took ten years to complete. This stunning tower gets its name from its first bell ringer, Giovanni di Balduccio, nicknamed ‘Mangiaguadagni’, which refers to a person who wastes money.

The Torre del Mangia is the best spot in Siena to enjoy incredible vistas. To do it, you just need to climb around 400 steps to reach the top of the tower, from where you can admire Piazza del Campo, Siena’s Cathedral, and the countryside in the distance.

Siena Cathedral

Among Italy’s most gorgeous cathedrals, Siena’s Cathedral or Duomo is much more than a church.

The building is part of a bigger complex which also includes the cathedral’s crypt and baptistery, a museum, the Piccolomini Library, the Oratory of San Bernardino, the Gate of Heaven, and the Panorama from the Unfinished Façade (or Facciatone in Italian).

Officially called the Cattedrale Metropolitana di Santa Maria Assunta, Siena’s Cathedral boasts a striking white-and-black marble outer appearance.

Inside, the cathedral is richly decorated with frescoed ceilings, marble floors, and magnificent works by famous artists Bernini and Michelangelo.

It gets busy, so I recommend buying your ticket in advance here, which will give you access to all the main areas.

Piccolomini Library

A must-visit, the Piccolomini Library is one of the gems of the cathedral. Located on the left-hand side of the nave, the Piccolomini Library used to be Pope Pius II’s private library, where he stored all the books he collected on his travels.

What’s really impressive about this room are the walls and ceiling, completely covered with early 16th-century colourful frescoes made by Pinturicchio and his pupils, including Raphael Sanzio.

The frescoes represent some scenes of the life of Pope Pius II, who was known more for his ambition than his devotion, as the abundance of shining gold accents in the library clearly states.

Museo dell’Opera

Another spot inside the Monument Complex of the Cathedral is the Museo dell’Opera, housed in the church’s right nave. The museum contains many original artworks moved from the cathedral’s main building for various reasons. The new location of these artworks helps in their conservation.

The museum displays unique masterpieces like Duccio di Buoninsegna’s ‘Maestà’, one of the most important pre-Renaissance works, and Donatello’s famous tondo with the Madonna and Child, known as the ‘Madonna del Perdono’.

The museum’s exhibition is split into three levels, with many marble statues, medieval manuscripts, and over 200 objects associated with the sacred liturgy.

Gate of Heaven

A visit to Siena’s Cathedral will not be completed without peeking through the Gate of Heaven, the amazing attic of the church. The only way to visit the Gate of Heaven is by joining a guided tour where an expert will lead you to a winding staircase in the corner of the cathedral up to the building’s starred-painted ceiling.

You will walk all around the cathedral through narrow corridors and outdoor passages, admiring the church’s decorations and the Tuscan hills. The Gate of Heaven is usually close to the public, so make sure to check the official website to plan your visit.

Historic Centre

Siena is a charming Medieval town, and its historic centre is a maze of winding streets that branch out from Piazza del Campo.

One of the best things to do in Siena is just strolling around its centre, where you’ll discover lovely squares, small churches, and lots of osterie (traditional restaurants serving local cuisine).

The intricate streets are pedestrian-only and are lined with beautiful Medieval and Renaissance buildings that speak of Siena’s glorious past. Not by chance, the town’s historic centre is listed as a UNESCO World Heritage Site, and walking around is a real journey back in time. Among the many buildings, the following three are particularly special.

Santa Maria della Scala

A museum complex with an important history, Santa Maria della Scala was one of Europe’s first hospitals. This building was opened in 898 and sits right before Siena’s Cathedral.

The placement is everything but random: Siena is along the via Francigena, the former pilgrimage route to Rome. In Santa Maria della Scala, pilgrims used to find lodging, and poor locals found shelter and cure.

Today, the complex is one of the biggest museums in Tuscany, with over 10,000 square meters of space. The museum is spread out over several levels, with many connecting hallways hosting stunning frescoes that are part of the museum’s extensive collection.

Basilica of San Domenico

Siena’s historic centre has another church you should consider visiting, the Basilica of San Domenico. Its construction began in 1226 but was completed only two centuries later, and it boasts an imposing Gothic architecture.

Dedicated to Saint Domenico of Guzmán, founder of the Dominican order, the Basilica contains beautiful masterpieces like the cycle of frescoes by famous painter Sodoma.

Inside the church, there is also the chapel of St. Catherine of Siena. Located on the right side of the central nave, the chapel keeps the head relic of the saint and is beautifully decorated with frescoes telling the story of St. Catherine.

Palazzo Buonsignori

Palazzo Buonsignori is another beautiful building in Siena’s centre. Built in late Gothic style for banker Giovanni Bichi Guccio, the palace changed owner a couple of times until it was purchased in 1476 by the Bonsignori family.

Today, the palace hosts the Pinacoteca Nazionale, a great gallery displaying the most representative works of the Senese painting school from the 13th to the 17th centuries. There are many other artworks inside Palazzo Buonsignori, in particular, a series of bas-reliefs and sculptures called the Loggia Sculpture and the Spannocchi – Piccolomini collection.

You can’t miss visiting Palazzo Buonsignori if you are an art lover!

Tours

Siena is pretty straightforward to explore on foot, but the town and its countryside offer many fabulous attractions that are awesome to visit by joining a tour. From walking tours to wine tastings to cooking classes, here are the best tours to do in Siena and around it.

City tours

Rather than just strolling around the maze of Siena’s streets, you can join a walking tour where an expert guide will lead you to discover multiple sights and secret spots.

This fantastic walking tour includes priority access to Siena’s Cathedral to uncover its stunning art and architecture while exploring the Torre del Mangia and the Basilica of San Domenico.

There are some other good city tours here I would suggest:

And another option is this walking tour with skip-the-line ticket where your guide will tell you about the history of the ‘contrade’ while touring Siena’s historic centre, which also includes a visit to Siena’s Cathedral.

Wine tasting

Tuscany is famous worldwide for its wine production, and one of the best wine regions is located in Siena’s countryside.

There is no better idea during your holiday than doing a wine-tasting tour. You can join many tours, but I suggest you book one that includes a local lunch, such as this one. During this tour, you can enjoy the rolling Montalcino hills while visiting three different Brunello wine-producing wineries.

Or there are some other good options here:

Besides touring the cellars and meeting the producers, you will taste delicious wines and a homemade Tuscan meal.

Cooking class

Tuscany is renowned for its cuisine, and learning to make fresh local meals is one of the best things you can do in Siena.

For an unforgettable time, join a cooking class on a beautiful farm in the Chianti wine region. This excellent cooking class is ideal for learning more about regional gastronomy before trying your hands on making pasta and desserts following the instruction of a local chef.

Another option is this farmhouse cooking class right in the heart of the Chianti area, where a local family will teach you many recipes passed down through generations.

Around Tuscany

Once you have finished exploring Siena, why not join a tour to discover the rest of Tuscany? There are so many tours that you are spoilt with choices!

A great idea would be to make your way to the towns of Pienza and Montepulciano with this full-day tour, during which you will walk around the two towns, touring ancient cellars, tasting local wines, and enjoying a traditional lunch at a dairy farm.

Or there’s this other fabulous tour will take you to the hilltop towns of San Gimignano and Volterra, admiring honey-coloured towers and alabaster workshops.