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The highlights of Siena, the most beautiful city in Tuscany

The highlights of Siena, the most beautiful city in Tuscany

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As far as we are concerned, Siena is the most beautiful city in Tuscany. The competition is great with so many beautiful places in the region but the highlights of Siena are so numerous that the city really deserves this honorary title. The grandeur that Siena had in the Middle Ages can still be admired here in all the streets, squares and churches. With the typical Italian atmosphere that the city has, you should not skip Siena when you visit Italy. It is not for nothing that the historical city centre is on UNESCO’s World Heritage list. We take you along to the highlights of Siena.


History of Siena

Before our era, the Etruscans founded a small settlement where Siena is today. In Roman times, the city was still not large and important. The heyday only came in the Middle Ages. Siena competed with neighbouring Florence in many fields. In the artistic field, they tried to surpass Florence. We still reap the benefits of this, because this competition has led to the most beautiful monuments that have been miraculously preserved.

In 1348, the plague broke out in Siena. The consequences for the city were disastrous. Many died of the “black death” and the city fell into decline. The prosperity of the Middle Ages has never returned.

Traditionally, Siena consists of 17 districts, the so-called contrade. Each district has its own flag and church. The world-famous horse race Palio on the Piazza del Campo shows the bitter struggle between the districts in full glory.

Palio competition

Siena’s absolute must-see highlights

The medieval city has with one of the most beautiful squares in the world and the magisterial cathedral, two major attractions. But besides that, you can find much more in and around the narrow streets. These are in our opinion the highlights of Siena that you should not miss during your visit:


Piazza del Campo

This is one of the most beautiful squares in Italy. Some even call it one of the most beautiful in the world. We dare not say so, but a visit to the Piazza is certainly one of the highlights of Siena.

The best way to see the square in its full glory is to take the stairs down through one of the narrow passages on Siena’s main street. Then you will also notice the beautiful, shell-shaped size of the square.

Around the square are the most beautiful buildings from the Middle Ages. On the square is the famous fountain Fonte Gaia. Around it, there are cosy terraces. A good place to have a nice cappuccino or lunch, but it is expensive. The famous landmarks Palazzo Pubblico and Torre del Mangia at the square will be described separately below.


Palazzo Pubblico

If you take the stairs from the main street to the square, you will immediately notice this building with the slender tower next to it. This building from the 14th century is still the town hall.

Fortunately, you can enter the town hall, as it houses the fantastic Museo Civico. Here, you will find a splendid and comprehensive overview of the masterpieces of Sienese painting. The museum shows the grandeur of Siena in the Middle Ages at its best.

Torre del Mangia

Right next to the Palazzo Pubblico is the Torre del Mangia. The bell tower was built around 1348. With its slender shape, it is the beacon of the square. The tower is about 100 metres high. You will have to take about 500 steps to get to the top. There, a magnificent view of the city and the surroundings awaits you. Unfortunately, it was not possible to visit the tower during Covid. Fortunately, there are other possibilities to have a beautiful view of Siena and the hinterland. We will tell you more about that.



Officially, the church is called Duomo Santa Maria. A visit to this sanctuary may not be missed if you visit Siena. First admire the beautiful facade of the church on the square. The facade decorations are so numerous, artful and detailed that you will enjoy it for a long time.

Inside, the magnificent marble mosaic floor catches the eye. Beautiful images can be seen here. Often the floor is covered in September to protect it, fortunately this was not the case here. The use of black and white marble gives the church a special atmosphere.

Be sure to buy a ticket not only to admire the interior of the church, but also the accompanying buildings: the splendid Piccolomini Library, the Baptistery (baptistery with the baptismal font) and the Museo dell’opera del duomo. Besides an impressive collection of religious objects, this museum is also worth a visit for another reason: a narrow corridor and a steep staircase lead to a viewpoint. From here, you have a magnificent panorama over the city and the hills near Siena. Due to corona measures, it took a very long time to finally reach the viewpoint. But we immediately forgot about those 2 hours of waiting when we got to the top.


Casa di Santa Caterina

This is the house where the canonised Caterina Benincasa lived between 1347 and 1380. At a young age, she had a vision that made her very religious. For the rest of her life, she lived according to the strict teachings of the Dominicans. She made an exception to one rule: she lived in her own house instead of the convent. Besides her good work for the sick, the poor and addicts, she was politically active. Not only in Siena, but even on the world stage. In 1461, the Pope canonised her. She is also the patron saint of Italy and the city of Siena.

The house has become a place of pilgrimage for believers. In the house you can see a number of beautiful chapels where she said her prayers daily.

Church in Siena

Church of San Domenico

Near the house of Santa Catarina stands this church. From the outside, the San Domenico looks robust, sober and simple. This is mainly due to the use of red bricks during construction. From the inside, one notices that it is a large space. That is why it is called a “hall church”. The church has a Santa Caterina chapel. Here lies the skull of the holy believer Catarina, with beautiful frescoes on either side depicting Catarina’s life.

From this church, you have a beautiful view of Siena Cathedral though we are going to give you an even better view below.


Fortezza Medicea

Do you want to escape the hustle and bustle of Siena’s narrow streets? Then visit this fortress just outside the centre. If you come to Siena by car, there is a good chance that you will park nearby. There are several large car parks here. So, make a trip to this fortress first. You will not see many tourists here. There are a lot of locals around who like going walking or jogging but mainly you can enjoy a fantastic panorama of the city. That’s why this is a nice place to come to. When the sun goes down, the view is even more beautiful!

Strolling through the narrow, steep streets

You can taste the medieval atmosphere of Siena best when you stroll through all the little streets in the city. The streets that lead to the Piazza del Campo in particular are sometimes narrow and steep. In all those streets, you will find the nicest shops and boutiques. And, of course, you can buy the most delicious Italian dishes in those shops. Be sure to try the sweet biscuits that Siena is known for. A true delicacy.

A little south of Piazza del Campo you will find Castelvecchio. This is the oldest part of the city. When walking through the streets, be sure to look up. The flags and other decorations will tell you which district you are in. You’ll also see the housewives deftly working the ingenious washing lines that they can operate from their flats.


Drinking coffee like an Italian

You can order an espresso or cappuccino on a sun-drenched terrace at Piazza del Campo, naturally. It’s even nicer to do this like a real Italian: walk into one of the many coffee shops and order on the spot. They often have the most beautiful cakes in their showcase. So, be sure to try one.

Drink the coffee standing at the bar. Listen to the heated conversations the locals have with each other or leaf through the pink sports newspaper “Gazzetta dello Sport”. It doesn’t get any more Italian than this.

Did you know that when you order your coffee like this, it is much cheaper than on the terrace? We had 2 cappuccinos and two delicious pieces of cake for just over €8. Plus, the experience of standing with the Italians like that is memorable.

More highlights of Siena

Above, we have mentioned our personal choice of highlights of Siena. But the city has many more wonderful sights to offer. Museum lovers will enjoy the Pinacoteca Nazionale. This is one of the biggest museums in the country. Or visit the intimate Piazza Salimbeni, surrounded by no fewer than three palaces. You can easily spend two days in Siena if you want to see all the sights.

Piazza Salimbeni

Visiting the highlights of Siena: practical information

With these practical tips, you can enjoy the highlights of Siena to the fullest:
How to get around Siena

Siena is surprisingly small. In the city, all attractions are located close to each other. You can easily reach all the highlights of Siena on foot. Only to the Fortress takes a little more time to get to.


If you travel to Siena by train, it is best to take the bus to the centre from the train station. The bus leaves from the terminal at the train station.

What is the best time to visit the highlights of Siena?

The best time to visit Siena is in spring or autumn. In the hot summer months of July and August, it is very busy in the city. However, for an introduction to the world-famous Palio, this is the right time.

Where to stay in Siena?

The city has enough accommodation in all price ranges. This is the overview of all hotels in Siena. And although you can visit Siena ideally as a day trip, a night in a hotel is definitely recommended. When all the day-trippers have left, the city shows itself at its best.


If you want to be in Siena around the time of the Palio (2 July and 16 August), it is important to book early. Bear in mind that on those days, rooms are more expensive. Some hotels are fully booked more than a year in advance.


We slept in a fine flat in Castelfiorentino ourselves. This place is centrally located in Tuscany. We could reach Siena quickly by train. But other cities in Tuscany could also be reached easily by train or car, which suited us nicely.