Siena Hidden Gems - Top 11 Things To Do
By Gillian Boyd Published 12 August 2026
Top 11 Things to do in Siena – Duomo, the world’s oldest bank, the Piccolomini Library – plus the famous Palio horse race that puts it on the map and more.
Siena is a compact city that can be explored in 3 days. Inside the thick old city walls few cars are permitted so it’s pedestrian friendly, though steep in places.
As we had a hire car, we were able to see the hilltop town of San Gimignano, Castello di Brolio castle and vineyard, and the small village of Fonterutoli and vineyard.
We stayed in an hotel with parking, just outside the city walls of Siena and walked in each day over the bridge and up the pedestrian friendly escalators which became our friend in the heat.
Siena Cathedral and Tower, Italy
Piccolimini Library inside Siena Cathedral
7 Top Things To Do in Siena
For me, THE TOP THING TO DO in Siena is to see the centuries old Palio horse race and historical procession on 2 July and 16 August and I have written a full guide on this.
It even appeared in the opening sequence of James Bond movie ‘Quantum of Solace.’ But if you are not in Siena for those dates, then these are my suggestions for you.
1. Siena Cathedral
Siena Cathedral, built in the 13th century is absolutely stunning and possibly my favourite Cathedral. Like other Duomos in the region, it has a highly ornate exterior, but to me it seemed to be more three dimensional, due to the many decorations and sculptures.
The sunlight just caught the gold on the 3 triangles at the top, at the perfect angle to really glow.
The steps of the Siena Cathedral (Duomo) are an excellent place to watch the Historical Procession of the Palio di Siena.
Michaelangelo Statues
Inside, Siena Cathedral is full of iconic black and white marble stripes on all the columns, stars on the ceiling and early marble statues by Michaelangelo. The themes are continued in the repeating patterns and colours of the intricate mosaics of Bible stories on the floor.
Piccolimini Library
But the best part for me, was the small Piccolimini Library with its brightly coloured Renaissance frescoes by Pinturicchio. On display were intricate gold leaf illuminated manuscripts of 15th century choir books.
Beside us, two young priests visiting, were testing out the choir sheets by humming the music as they moved from cabinet to cabinet. Such a perfect moment that I barely noticed The Three Graces statue as we left smiling.
Facciatore Observation Platform in Siena, Italy
2. Facciatone
Next to Siena Cathedral is the Facciatone, the unfinished nave of Siena’s abandoned 14th century extension. There is an observation point with views over Siena. It reminded me of Salvador Dali, with its arches against a clear blue sky.
Clay laid in Piazza del Campo for the Palio di Siena
3. Piazza del Campo
The main square in the centre of Siena is not square, nor flat at all. The Piazza del Campo is shell shaped, slopes significantly and is the site of the historic Palio di Siena horserace which has been running since the 12th century.
The piazza is covered in clay twice a year for races on 2 July and 16 August (weather permitting). There are 6 Official Trial Races in the preceding 3 days. It is very exciting to watch and attracts crowds of over 50,000 people crammed into the piazza.
If you are visiting at another time of the year, still go and see the piazza. It is unique.
Crowd in Piazza del Campo at Palio di Siena in front of Torre del Mangia and Palazzo Pubblico
4. Torre del Mangia
At 88m tall and standing next to the Palazzo Pubblico, the Torre del Mangia dominates the skyline of the Piazza del Campo in the centre of Siena.
Symbolic Balance
It was designed to match the height of the bell tower of Siena’s Cathedral – symbolizing the balance in power between civic and religious authorities. Oh if only life was that simple!
If you want to reach the top of this 14th century gothic bell tower you need to climb about 400 narrow stone steps. Tickets can only be bought in person at the Palazzo Pubblico ticket office.
The Entrone of the Palazzo Pubblico in Siena
5. Palazzo Pubblico
Beside the Piazza del Campo is the Palazzo Pubblico, the medieval town hall for Siena.
See the Entrone, a large entrance with vaulted archway within the Palazzo Pubblico, where the competing horses of the Palio di Siena emerge for the start of the race. Notice the hooks on the wall, which were historically used for tethering animals or hanging tapestries or banners.
Imagine what the atmosphere is like with 50,000 people waiting just beyond the archway. Or see around the Civic Museum housed inside.
Piazza Salimbeni in Siena, Italy
6. Piazza Salimbeni
See the Piazza Salimbeni hemmed on 3 sides by palaces, where the headquarters of the oldest continuously operating bank in the world, the Banca Monte dei Paschi di Siena, is based.
Living proof of the importance of Siena throughout history.
View of Siena and the Cathedral from the Giardini Pubblici
7. Fortezza Medicea and Giardini Pubblici
The Medici Fortress was built in 1561-3 by Duke Cosimo, who later became the first Grand Duke of Tuscany. He was part of the Medici family and was very powerful in Florence too, commissioning great pieces of public art there.
Today the Fortezza Medicea is a free public park, and hosts a Jazz Festival and concerts. There are also good views of Siena too.
Towers of San Gimignano, Tuscany
4 Hidden Gems Near Siena
Whilst we were based in Siena, we visited these places using our hire car. However they are still easily accessible if you are based in other parts of Tuscany. See Montepulciano for information on Pienza, Montalcino and Monticchiello.
1. San Gimignano
About 50 minutes drive from Siena is San Gimignano, a beautiful hill top town with many cute and stylish shops. It is known as the ‘town with 5 towers’, although in reality there are 14 still standing from the 72 that existed in the 14th century.
Parking
We entered the town through the large arched gateway having parked in Car Park 1 and walked uphill for about 10 minutes.
Parking was by the hour up to a max of €7 for the day and there was a little shuttle bus if you needed it. There are several car parks around the outskirts of the town and Car Park 1 seemed to be the farthest away.
Musican playing in courtyard in San Gimignano, Tuscany
Shops
After a little bit of shopping (well, Italians are known for their style), we went up the cobblestone streets to the square where we stopped for an Italian lemon soda and some people watching. There was a buzz about the place with some tourists but not too many big tour groups.
Climb the Tower
We climbed the tallest tower, the Torre Grossa at 54m for views over the hill town and out to the mountains beyond. We got chatting to the man working at the top and learned we were looking at the same 3 mountain ranges we had seen in Lucca – the Apuan Alps, the Apennines and the Monte Pisano. Also the Elsa Valley and of course, the Chianti Vineyards.
Live Music
As we wandered around the town we stepped into one large courtyard to the sound of a harpsichord like instrument. The music increased in volume and tempo and I felt like I had walked into a movie. The musician appeared shy, for he stood with his back to the courtyard.
Dante
Later in the square, under the shade of the arches, a man in medieval costume with red velvet cloak, recited Dante’s Divine Comedy in a wonderful deep Italian baritone voice to the passing crowd, his tip box standing proud.
The musician and the performer created an atmosphere that helped me to imagine being in the town hundreds of years ago.
Gunblast damage on the walls of Castello di Brolio, Tuscany
2: Castello di Brolio
About 30 minutes drive from Sienna is the Castello di Brolio where we tasted wine and had a tour.
Lunch
But first, we had lunch at a delightful small old family run restaurant, Il Carlino D’Oro, overlooking the Castello Brolio vineyards.
There we ate the white boar cintra ragú and classic tagliteli ragú. Both were very good. The attentive waiter had even divided the pasta dishes for us onto two plates as we had mentioned we were sharing.
Steep Climb
After lunch we walked from the Castello Brolio car park up through a short, steep forested trail.
This historic vineyard is on a hill (of course) and still has a castle standing despite repeated attacks over the centuries.
The blasts of gunfire damage were clearly visible, like scars from an adventurous life. What stories those walls could tell!
Formal garden of Castello di Brolio, Tuscany
Formal Garden
In front of the castle, the views stretch for miles and then when you look down there’s a surprise – a formal garden of box hedges at the base of the protective wall, so close that you could look over it to the views beyond and miss it as I did! ‘Look down’ called Graham and there it was.
After exploring the grounds and the open parts of the castle, we descended through the forest again to the tasting room beside the road, for the glass of wine included with our entrance fee.
Eroica
In the tasting room, we spotted that Castello di Brolio sold a merino wool cycling top and by chatting to the host, we learned that it is popular with contestants in the Eroica bike race.
People often wear vintage or retro inspired clothing when completing the race, as it is completed on old bikes. One has to be heroic to complete it!
The visit to Castello di Brolio was a lovely mix of views, gardens, history and wine, so it was one of my favourites. If you only have time for one vineyard visit, then do this one.
Stone buildings in Fonerutoli, Tuscany
3. Fonterutoli
Fonterutoli is a pretty small village on the SR222 Chianti route. It’s a tiny village just south of the hilltop town of Castellina in Chianti and is known for two things – the Fonterutoli vineyard and the Via Romea Sanese.
Pilgrimage Hike
Usually divided into 4 sections, the Via Romea Sanese pilgrimage hiking trail from Florence to Siena is 78km long. Fonterutoli village is one of the stopover points as it has some accommodation for hikers. Have you ever noticed how often hiking trails were originally pilgrimage routes?
Fonterutoli Wine Tasting
After wandering around the village, we stopped at the Castello Fonterutoli for a wine tasting.
Sadly, there is no longer a castle as this was destroyed a long time ago, but the name Castello is still used because it signifies that the grapes used are from that vineyard only.
The White Whale limestone formation at Bagni San Filippo Hot Springs, Tuscany
4. Visit Bagni San Filippo Hot Springs
For something completely different, we highly recommend a visit the natural thermal baths at Bagni San Filippo about 66km or 1 hour 15 mins from Siena by car.
The hot springs are surrounded by lush forest, completely natural made from limestone formations. The largest and most famous is the white whale and you can bathe for free in the pools.
Read our full guide including water temperatures, where to bathe and tips on parking in Bagni San Filippo Hot Springs.
Final Thoughts
Siena was more than just the oldest horse race, the Palio and the oldest continuous bank in the world. As a medieval powerhouse to rival Florence, it has its own profusion of architectural landmarks to impress us all.
It’s a compact city full of nooks and crannies to explore, discovering restaurants, shops, and locals. Siena had cheeky children practising their English and entrepreneurial skills, always with a smile on their face.
I had wondered if the festive atmosphere and general buzz about the place was due to the Palio, but others I have met, who visited at in different months, confirmed that they also had a soft spot for Siena.