How often have you been to Siena and just seen the Duomo, or maybe the Allegory of Good Government fresco, and then moved on to your next destination? It’s always easy to see the most famous things in the city, and to want to see them multiple times. It takes research, and more time in town, to see stuff that is a bit off the beaten track. But you probably know that it’s worth the effort!
Having been to Siena a bunch of times as a day trip from Florence and always seen the same things, I decided to look into what Siena offers beyond the Duomo and the Campo. On a quiet winter’s day, I found myself quite alone in all the places I discovered – what a pleasure!
Siena off the beaten track itinerary on a map and in video
Explore the locations listed below on the map – they look further apart than they are, you can easily walk to all of these places in the course of a day-long visit, though the longer you stay, the more time you have to get to know the city.
This short video is a preview of what is written below, though I couldn’t fit it all in the video!
Monte dei Paschi di Siena – Palazzo Salimbeni
Ok the Monte dei Paschi is hardly a hidden gem but did you know that this palazzo is the headquarters of the oldest bank in Europe? It was founded in 1472 as a charitable institution, a “monte di pietà”, and then became a commercial bank in 1624. The Monte dei Paschi has been an important supporter of cultural life in Siena over the years, though sadly due to recent economic problems they have had to step back from this role.
The building, Palazzo Salimbeni, is in the Sienese Gothic style and was the home of the richest family in Siena (like, where the King’s brother and the Emperor stayed when they visited back in the Middle Ages) until being purchased by the bank in 1866. On the front of the Palazzo is a wide bench that would have been where people appealing to the wealthy family, and then to the bank, would have sat and waited their turn. This was a common feature of Medieval banks in general, and in fact the street names Via Banchi di Sopra and Via Banchi di Sotto, get their names from one of the city’s most widespread trades, that of the moneychanger, where one expects there were lots of… benches. And waiting in line.
Basilica of San Domenico – relics of Saint Catherine of Siena
If you’ve parked up at the Stadium or Fortezza parking you probably have walked past and maybe into this church plenty of times – I certainly have. The large basilica dominates this side of the city up on the hill but frankly its interior doesn’t offer much that I find interesting – due to fires and earthquakes over the years – except the chapel and relics of Santa Caterina of Siena.
Catherine died in 1380 at 33 years old from the fasting and penances she inflicted on herself in the name of her mystical husband Jesus. She was buried in Rome, but in 1381 her head was detached from her body at the behest of Pope Urban VI and donated a year later to the Sienese – as one does… The mummified head was placed in this chapel in the church of San Domenico, surrounded by frescoes by Il Sodoma showing scenes from her life. Another reliquary on the right wall of the church preserves her right thumb and the cords with which she whipped herself.
Fontebranda
At one of the lowest points of the city is a large medieval fountain famously mentioned by both Dante and Boccaccio. It looks like a mini castle with its crenelated top and three gothic-arched bays. The three bays contained progressively less clean water for drinking, washing, and animals.
Santa Maria della Scala
Although this large museum in piazza Duomo is smack dab in the middle of town, when I visited it was completely empty. Santa Maria della Scala was, until not long ago, the city’s main hospital – children born here were held up to the window so they could see the Duomo! Besides being an absolutely sprawling and unheated space, it also has numerous layers of history.
The Pilgrims hall on the ground floor is what I’d consider the main destination here: a frescoed masterpiece that speaks of the charitable acts undergone for pilgrims here on the via Francigena as they passed through the medieval city. The large pictorial cycle dates to the 1440s by Domenico di Bartolo, Lorenzo di Pietro known as il Vecchietta, and Priamo della Quercia. There is no wall text beyond the title of each scene, so you have to spend some time gazing up to “read” what is going on. While there are some mythological scenes, my favourite ones are those that picture the activities that took place here, such as clothing and feeding the poor, caring for the sick, assisting young women without dowries, and paying for wetnurses for orphans. These are typical scenes of assistance that we see in other fresco cyles of the Renaissance (one of my particular intersets).
There are two lower levels in this building that lead you to various collections, including a large archaeological collection that I don’t believe anyone ever visits. But the most fascinating parts, in my opinion, are three confraternal chapels. Confraternities are associations of lay people – usually men – dedicated to a specific saint and sometimes with specific functions like consoling the sick. On the first basement level of this building is the Oratory of the Confraternità di Santa Caterina della Notte. Members of this confraternity prayed for those who died in the hospital, and set up shop quite near the hospital’s cemetary. Saint Catherine herself used to come to comfort the sick and pray for the dead, and the confraternity and it’s dark rooms reflect this same religious fervour. The stucco decorations are from the 16th century while a marble Madonna on the altar is from the 13th. You can see lists of names of confraternity members, and their tools – the rosary and cords with which to flagellate themselves.
Pinacoteca Nazionale
The staff at the national painting museum (Pinacoteca nazionale) of Siena looked rather surprised to see me, a rare visitor to a museum currently undergoing a rather major restoration. Perhaps I might have skipped it for this reason, because in fact the most important Sienese paintings are not on view. They’ve selected the three highlights of the collection by Duccio and Ambrogio Lorenzetti for display in a small room on the main floor. Upstairs is an unusual collection of small, portable works that were used by confraternities in processions, as well as later works from the Sienese Renaissance. The museum is closed from January 26th 2026 with no reopening date announced as of yet.
Collegiata Provenzano
When a terracotta bust of the Madonna was shot by a carousing Spanish soldier and began producing miracles, the Madonna di Provenzano became central to the city’s Marian devotion. The late 16th-century church built up on the location of the original tabernacle who is now ensconsed in silver and gold as part of an ornate altarpiece.
The palio of July 2 is also connected to this space: it is run in honour of the Madonna di Provenzano, and the drappellone, or palio – a processional painted cloth – is hung here under the dome of the church on the night before the palio.
Synagogue of Siena
The recently reopened Synagogue of Siena was an eye-opening surprise for me. Siena’s Jewish community is one of the oldest in Tuscany, with the first documents attesting to the presence of Jews in Siena dating back to 1229. It is a ghetto place of worship, so it doesn’t have a grand entrance but is rather hidden behind a normal house façade. The area of worship is located upstairs in a light-filled space of Rococo décor. The womens’ gallery looks into the main space of the synagogue through latticework, and it’s a rare privilege to be able to access spaces like this.
The synagogue, still used for religious services by the local Jewish community, houses ancient Torah scrolls, silverware and ritual vestments of great value. Inside is also the Elijah seat, a liturgical piece of furniture enriched with biblical inscriptions. Two commemorative plaques were affixed next to the synagogue door. The first was placed there on 5 December 1948, in memory of the fourteen Sienese Jews deported and killed in the Nazi extermination camps during the Holocaust. The second was added on 28 June 1999, on the bicentenary of the 28 June 1799 when thirteen Sienese Jews were burnt alive during the devastation of the Sienese ghetto by Viva Maria supporters.
Fonte del Casato
Siena has a few majestic fountains and this really is not one of them, but I wanted to see it due to it’s rather macabre history. This fountain, essential to provide homes in the area with water, was built between 1352 and 1360. Due to many suicides here, they tried repeatedly to bless it. It is also linked to a gruesome legend about a fight between a wolf and a man. The story is rather vague, you can read it here. In person, you can see how this basin is place well below the level of the next street above it, and also accessed by numerous stairs from its street, so you can imagine it was quite the flight downwards if one were so inclined.
Vicolo Degli Orbachi
The Vicolo degli Orbachi is a little street in the Bruco (worm) contrada of Siena. There’s the contrada’s fountain located under the slight bridge of the street that runs above here, where there’s a modern sculpture. But what brought me here was the naked lady in the window, 24/7. This a work by artist Pier Luigi Olla from 1995. Fun, clever and a bit mysterious.
Ex ospedale psichiatrico di San Niccolò
I didn’t make it all the way beyond the city walls to visit this ex psychiatric hospital on my latest visit, but it’s on my list. This building was a monastery from 1300 to 1810 and then a hospital from 1818 to 1999. Yes you read that correctly, 1999. A large iron sign at the entrance indicates its denomination as “Ospedale Psichiatrico”. The grand building was developed in line with sincere beliefs of the role of space as part of the cure, and as moral remedies. It was to look like a grand villa, with vast gardens; evertyhing to try to hide its institutional nature. The space now hosts the university of siena’s department of computer engineering , political social science, and the physics department in the basement ex-laundry area – scary stuff.
Museo delle Biccherne
My favourite totally off the beaten track museum in Siena is the Museo delle Biccherne, part of the state arhive, but it is only open with reservation Saturday mornings at 10am. If you ever get the chance to visit, this is where you can marvel at shelves full of thick, hand-bound vellum and parchment bindings. The biccherne are painted covers of the registers of various Sienese magistrates from the middle ages to the beginning of the 18th century, often commissioned from important artists. There are over 100 of these highly unique items.
The tiniest window
On the façade of Palazzo Della Rovere in the central piazza Postierla is what the Sienese say is the tiniest window in Siena, but I’m willing to bet it’s the only thing like it in all of Italy. A local friend pointed this out to me. What’s the story here, we don’t know, but this is a real opening that is dwarfed by the normal sized window next to it, complete with matching grey-painted shutters that open
