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The Secrets of Siena

Where Medieval Rivalry Meets Renaissance Splendour

Perched on three hills in the heart of Tuscany, Siena is the city that dared to rival Florence and nearly won. Its shell-shaped piazza has hosted the thundering Palio horse race since the 1600s. Walk through 800 years of civic pride, artistic genius, and neighbourhood warfare — from the world's oldest hospital to a tower named after a man who ate his wages. Ten riddles stand between you and the title of true Sienese insider.

10
Stops
~2h
Journey
10
Riddles

How to Play

  1. Tap a stop to read its story
  2. Solve the riddle — tap your answer
  3. The truth (+ hidden history) is revealed!
  4. Tap the 📍 address to navigate via Google Maps
The Republic of Siena
The Shell That Holds a City's Soul

A sloping piazza shaped like a scallop shell, divided into nine segments for the nine magistrates who once governed the republic.

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Piazza del Campo
Medieval · 13th Century
📍 Piazza del Campo, 53100 Siena SI
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📖 The Story
You step into one of the most breathtaking public spaces on Earth. Piazza del Campo fans out before you in a great shell shape, its red-brick paving tilting gently toward the Palazzo Pubblico like a natural amphitheatre. The nine segments you see etched into the ground represent the Council of Nine, the merchant-led government that ruled Siena during its golden age from 1287 to 1355.

Twice a year, this elegant piazza transforms into a thundering racecourse. Earth is spread across the stones, mattresses pad the sharpest corners, and ten jockeys ride bareback for roughly ninety seconds of pure chaos known as the Palio.
🧩 Riddle
How many segments divide the paving of Piazza del Campo?
💡 Need a hint?
Think about the medieval government that ruled Siena at its peak.
🎉 The Answer
B. Nine
The nine segments honour the Governo dei Nove (Government of Nine), the merchant oligarchy that ruled Siena from 1287 to 1355 and commissioned most of the city's greatest buildings.
The Art of Governance
Where Frescoes Taught the Art of Ruling

A Gothic palace built to house the republic's government, its walls covered with history's first political propaganda.

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Palazzo Pubblico & Museo Civico
Gothic · 1297–1310
📍 Piazza del Campo 1, 53100 Siena SI
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📖 The Story
The Palazzo Pubblico rises at the foot of the Campo like a stern but graceful guardian. Built between 1297 and 1310, it was the seat of Siena's republican government and remains the city hall to this day. Step inside the Museo Civico and you encounter something remarkable: Ambrogio Lorenzetti's Allegory of Good and Bad Government, painted in 1338–1339.

This is not decoration — it is instruction. The frescoes were placed in the room where the Nine actually met, so they would be forced to stare at the consequences of their decisions every single day. Good Government shows a prosperous city with dancing citizens. Bad Government depicts tyranny, ruin, and fear.
🧩 Riddle
What famous fresco cycle inside Palazzo Pubblico depicts the effects of just and unjust rule?
💡 Need a hint?
It was painted by Ambrogio Lorenzetti in 1338–1339.
🎉 The Answer
B. Allegory of Good and Bad Government
Lorenzetti's Allegory of Good and Bad Government (1338–1339) is considered the first purely secular fresco cycle in Western art. It was painted in the Sala dei Nove, where the ruling council actually met.
The Skyline Wars
The Tower Named After a Glutton

A 102-metre tower built to match the cathedral's height, proving that in Siena, church and state stood as equals.

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Torre del Mangia
Medieval · 1338–1348
📍 Piazza del Campo 1, 53100 Siena SI
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📖 The Story
Rising beside the Palazzo Pubblico, the Torre del Mangia soars 102 metres into the Tuscan sky, making it one of the tallest medieval towers ever built in Italy. Its construction took a full decade, from 1338 to 1348, and it was deliberately designed to be the same height as the cathedral across town — a bold statement that civic power equalled religious authority.

The tower's curious name comes from its first bell-ringer, Giovanni di Balduccio, nicknamed 'Mangiaguadagni' — literally 'profit eater' — because he was famously bad with money. Over 400 steps lead to the top, where a panoramic view sweeps from the city's terracotta rooftops to the rolling Tuscan hills beyond.
🧩 Riddle
Why is the Torre del Mangia named 'Mangia'?
💡 Need a hint?
It has to do with the first person who rang the tower's bell.
🎉 The Answer
B. Its first bell-ringer was a notorious spendthrift
Giovanni di Balduccio, the tower's first bell-ringer, was nicknamed 'Mangiaguadagni' (profit eater) because he spent all his wages on food and drink. An automaton carved in his likeness once struck the hours.
The Cathedral Builders
The Church That Tried to Swallow a City

A black-and-white marble cathedral so ambitious the Sienese tried to double its size — then the plague arrived.

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Duomo di Siena
Romanesque-Gothic · 1215–1263
📍 Piazza del Duomo 8, 53100 Siena SI
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📖 The Story
The Duomo di Siena hits you like a wave of zebra-striped marble. Its alternating bands of black and white stone reference Siena's legendary founders — Senius and Aschius, sons of Remus — who supposedly rode horses of those colours. Designed between 1215 and 1263 by Nicola and Giovanni Pisano, the cathedral is a masterwork of Italian Gothic architecture.

But the truly extraordinary story is what almost happened. In 1339, the Sienese began a massive expansion that would have made this cathedral the largest in Christendom. Then the Black Death of 1348 wiped out over half the population. The grand project was abandoned, and you can still see the unfinished walls standing as a haunting monument to interrupted ambition.
🧩 Riddle
Why was the planned expansion of Siena's cathedral never completed?
💡 Need a hint?
A catastrophic event struck Europe in 1348.
🎉 The Answer
B. The Black Death devastated the population
The Black Death of 1348 killed more than half of Siena's population. The unfinished nave walls, called the Facciatone, still stand today and offer one of the best viewpoints in the city.
The Renaissance Cradle
Where Five Masters Forged a Font

Hidden beneath the cathedral, a baptistery whose font was sculpted by the greatest names of the early Renaissance.

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Battistero di San Giovanni
Gothic · 1316–1325
📍 Piazza San Giovanni, 53100 Siena SI
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📖 The Story
Descend the stairs behind the cathedral and you enter the Battistero di San Giovanni, built between 1316 and 1325 by Camaino di Crescentino beneath the extended choir of the Duomo. The space feels almost secret — a vaulted crypt painted with vivid frescoes by Vecchietta (Lorenzo di Pietro), completed between 1447 and 1450.

But the centrepiece is the extraordinary hexagonal baptismal font, created between 1417 and 1431. The panels were sculpted by a veritable dream team of early Renaissance masters: Donatello, Lorenzo Ghiberti, Jacopo della Quercia, and Giovanni di Turino.
🧩 Riddle
Which of these Renaissance masters did NOT contribute a panel to the baptismal font?
💡 Need a hint?
Think about which sculptor is more associated with Florence and painting ceilings.
🎉 The Answer
C. Michelangelo
The baptismal font brought together Donatello, Ghiberti, Jacopo della Quercia, and Giovanni di Turino. Donatello's panel depicting Herod's Feast is considered a breakthrough in Renaissance relief sculpture.
The Age of Mercy
Europe's Oldest Hospital

A thousand-year-old hospital turned museum, where frescoes once comforted the sick and celebrated charity.

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Santa Maria della Scala
Medieval · 9th–20th Century
📍 Piazza del Duomo 1, 53100 Siena SI
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📖 The Story
Directly opposite the cathedral stands Santa Maria della Scala, one of Europe's oldest hospitals, founded around the 9th century to care for orphans, pilgrims, and the sick. For over a millennium it served as a centre of Sienese civic charity before closing as a hospital in 1995 and reopening as a museum.

The Pellegrinaio (Pilgrims' Hall) contains stunning frescoes from the 1440s by Domenico di Bartolo depicting daily hospital life — surgeons at work, children being nursed, and food being distributed to the poor. Below ground, you descend into the original Etruscan and Roman archaeological layers.
🧩 Riddle
What was Santa Maria della Scala before it became a museum?
💡 Need a hint?
It served the city for over a thousand years in a caring capacity.
🎉 The Answer
C. A hospital
Santa Maria della Scala operated as a hospital for over 1,000 years, making it one of the oldest in Europe. It also houses the original marble panels from the Fonte Gaia fountain, carved by Jacopo della Quercia between 1409 and 1419.
The Water Wars
The Fountain That Made a City Rejoice

A marble fountain at the top of the Campo, fed by underground tunnels and named for the joy it brought when water first arrived.

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Fonte Gaia
Renaissance · 1409–1419
📍 Piazza del Campo, 53100 Siena SI
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📖 The Story
At the top of Piazza del Campo sits the Fonte Gaia — the 'Fountain of Joy' — named for the celebrations that erupted in 1342 when water first reached this spot via a complex system of underground tunnels called bottini. The fountain you see today is a 19th-century replica by Tito Sarrocchi, installed in 1869.

The original was sculpted between 1409 and 1419 by Jacopo della Quercia, Siena's greatest Renaissance sculptor. Its panels depicted the Virgin Mary flanked by the Virtues — a civic reminder that good governance flows from moral character, just like water flows from the hills.
🧩 Riddle
What does 'Gaia' mean in the name Fonte Gaia?
💡 Need a hint?
Think about what people felt when water finally reached the piazza.
🎉 The Answer
C. Joy
The name Fonte Gaia (Fountain of Joy) refers to the celebrations in 1342 when water first flowed into the Campo through the bottini — a 25-kilometre network of underground aqueducts, much of which is still intact.
The Sienese School
The Painters Florence Tried to Forget

A gallery dedicated to the Sienese masters who rivalled Florence but chose beauty over realism.

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Pinacoteca Nazionale
Gothic–Renaissance · 14th–17th Century
📍 Via di San Pietro 29, 53100 Siena SI
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📖 The Story
Housed in the 14th-century Palazzo Buonsignori, the Pinacoteca Nazionale is the definitive collection of Sienese painting from the 12th to the 17th century. While Florence chased perspective and anatomical precision, Siena's artists — Duccio, Simone Martini, the Lorenzetti brothers — pursued something different: luminous gold grounds, sinuous lines, and an almost mystical emotional intensity.

Duccio's works here laid the groundwork for the entire Sienese school. The gallery tells a story of a parallel Renaissance — one that valued grace and spiritual beauty over scientific naturalism.
🧩 Riddle
Which painter is considered the founder of the Sienese school of painting?
💡 Need a hint?
His greatest work, the Maestà, once graced the cathedral's high altar.
🎉 The Answer
C. Duccio di Buoninsegna
Duccio di Buoninsegna (c. 1255–1319) is considered the founder of the Sienese school. His Maestà altarpiece was carried from his workshop to the cathedral in a joyous public procession in 1311.
The Mystic's City
The Church That Keeps a Saint's Head

A vast Gothic basilica where Catherine of Siena prayed, and where her preserved head rests to this day.

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Basilica di San Domenico
Gothic · 1226–1265
📍 Piazza San Domenico 1, 53100 Siena SI
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📖 The Story
The imposing Basilica di San Domenico dominates Siena's western skyline, its austere brick walls rising from the hillside since 1226. The church was expanded through the 14th century in the Cistercian Gothic style, creating the vast, unadorned nave you see today.

This is the church of Saint Catherine of Siena (1347–1380), one of only four female Doctors of the Church. She experienced her first vision here at age six. The Chapel of Saint Catherine contains her preserved head in a gilded reliquary, along with frescoes by Sodoma (Giovanni Antonio Bazzi) depicting her mystical experiences.
🧩 Riddle
What remarkable relic of Saint Catherine is preserved in the Basilica di San Domenico?
💡 Need a hint?
It is kept in a gilded reliquary in her dedicated chapel.
🎉 The Answer
B. Her preserved head
Saint Catherine's preserved head was brought to Siena in 1384, four years after her death in Rome. Her body remains in Rome at Santa Maria sopra Minerva. She is one of only four female Doctors of the Church.
The Fall of the Republic
The Fortress That Buried a Republic

Built by the Medici after conquering Siena, this star-shaped fortress now hosts wine tastings where soldiers once stood guard.

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Fortezza Medicea
Renaissance · 1561–1563
📍 Viale Venticinque Aprile, 53100 Siena SI
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📖 The Story
Your journey ends at the Fortezza Medicea, a star-shaped fortress built between 1561 and 1563 by order of Cosimo I de' Medici after Florence finally conquered the Republic of Siena in 1555 following an 18-month siege. It was designed as a symbol of Florentine dominance over the proudly independent Sienese.

Today, the fortress has been reclaimed by the city. Its bastions offer sweeping views of the Tuscan countryside, and inside you will find the Enoteca Italiana, a wine-tasting venue housed in the old munitions vaults. What was built to suppress Siena's spirit has become one of its most beloved public spaces.
🧩 Riddle
Who ordered the construction of the Fortezza Medicea after Siena's defeat?
💡 Need a hint?
He was the Grand Duke of Tuscany and a member of Florence's most powerful family.
🎉 The Answer
C. Cosimo I de' Medici
Cosimo I de' Medici built the fortress after the fall of the Sienese Republic in 1555. The siege lasted 18 months and reduced the population from 40,000 to around 8,000. Today the fortress houses the Enoteca Italiana.

✨ Must-Do List

Beyond the 10 stops

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Climb the Facciatone
Scale the unfinished wall of the cathedral's abandoned expansion for the best panoramic view in Siena.
📍 Piazza del Duomo, Siena
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Explore the Bottini
Guided tours of Siena's medieval underground aqueduct system — 25 km of hand-dug tunnels beneath the city.
📍 Various access points, Siena
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Day Trip to Val d'Orcia
The UNESCO-listed landscape south of Siena — rolling hills, cypress-lined roads, and Pienza's famous pecorino.
📍 Val d'Orcia, Tuscany
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Orto Botanico dell'Università
A peaceful botanical garden tucked behind the university, perfect for escaping the crowds with a book.
📍 Via Pier Andrea Mattioli 4, Siena
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Accademia Musicale Chigiana
Summer concerts in the stunning Palazzo Chigi-Saracini. World-class chamber music in an intimate medieval setting.
📍 Via di Città 89, Siena
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Wednesday Market
Every Wednesday near Fortezza Medicea, locals shop for produce, cheese, leather goods, and clothing.
📍 Viale XXV Aprile, Siena
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Chianti Wine Road
Drive the SS222 between Siena and Florence through rolling vineyards, medieval hamlets, and family-run wineries.
📍 SS222, Chianti Region

"Cor magis tibi Sena pandit" — Siena opens its heart wider to you

Est. 1240 · Lupa Senese
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