🇮🇹 Italy · Central Italy (Lazio and Tuscany)
Few cities carry you into the past like Siena. Perched on its hills in the heart of Tuscany, it keeps one of the most complete and beautiful medieval centres in Europe: a maze of reddish brick lanes, Gothic palaces, stone coats of arms and squares that seem stopped in the 14th century. Walking Siena means stepping right into the Middle Ages, when it was one of the richest and most powerful cities in Italy, a formidable rival to neighbouring Florence.
Its heart is the Piazza del Campo, one of the most extraordinary squares in the world: an enormous sloping brick shell, divided into nine sectors, presided over by the slender Torre del Mangia and the Palazzo Pubblico. It is the stage for the Palio, the thrilling horse race in which the contrade — the city's historic districts, with their flags, colours and centuries-old rivalries — compete twice a year in an explosion of passion that defines Sienese identity. And a few steps away rises the Duomo, a symphony of black and white marble, with its sculpted façade, its mosaic floor and the dazzling Piccolomini library.
This guide covers the essentials of Siena with a practical, warm eye: how to climb the tower, what to see in the cathedral, how to understand the Palio and the contrade, where to eat pici and the typical sweets, and how to use the city as a base for discovering the incomparable Tuscan landscape of vineyards, cypresses and storybook villages around it. Siena is one of those cities that stay with you for good.
According to legend, Siena was founded by Senius and Aschius, sons of Remus (the brother of Romulus, founder of Rome); that is why the Roman she-wolf suckling the twins is also the city's symbol. Beyond the myth, there was an Etruscan settlement and later the Roman colony of Saena Iulia. But Siena's great moment was the Middle Ages: between the 12th and 14th centuries it became a prosperous independent republic, a banking power (the Monte dei Paschi di Siena, considered the oldest bank in the world still in business, founded in 1472, operates here) and a commercial rival of Florence. In 1260, the Sienese won a resounding victory over the Florentines at the battle of Montaperti. That splendour crystallised in the so-called Government of the Nine (1287-1355), which gave the city its harmonious town planning, the Piazza del Campo, the Palazzo Pubblico and an extraordinary artistic flowering, with masters of Sienese Gothic such as Duccio di Buoninsegna, Simone Martini and the Lorenzetti brothers. The Black Death of 1348 was a devastating blow the city never fully recovered from. After centuries of decline and struggle, Siena finally fell to Florence and the Empire in 1555, and was absorbed into the Medici Grand Duchy of Tuscany. That defeat, paradoxically, froze the city in its medieval form, which has come down to us almost intact. In 1995, the historic centre was listed as a Unesco World Heritage Site. The full story is on our history page.
Read the full history ↓The historic heart of Italy: Rome and Lazio, cradle of the Empire and seat of the papacy; the Tuscany of the Etruscans, the communal republics of Siena and Pisa, and Florence, the city that gave the world the Renaissance.
Read the history of Central Italy (Lazio and Tuscany) →No exact prices: a scale from $ (budget) to $$$$$ (luxury), with 2-3 options per category.
Origins, formation and what the sources say.
Like many Italian cities, Siena has a founding legend that links it to Rome. According to the myth, the city was founded by Senius and Aschius, the sons of Remus, brother of Romulus (the founder of Rome). Fleeing their uncle Romulus, the young men are said to have reached these hills riding one white horse and one black, and to have founded the city there, bringing with them the statue of the Capitoline she-wolf that suckled their father. That is why Siena's symbol, like Rome's, is the she-wolf suckling the twins, an image repeated on columns and fountains all over the city. Tradition also traces the name to 'Senius', and the black and white of the coat of arms and of the Duomo to those two horses.
Beyond the legend, archaeology indicates there were settlements in the area from Etruscan times, taking advantage of the high, defensible position of the hills. Under Roman rule there was a colony here, Saena Iulia, probably founded in the time of the emperor Augustus, though it was a minor centre compared with other cities of Roman Etruria.
Siena's real greatness came not in Antiquity but in the Middle Ages. The city benefited from its position on the Via Francigena, the great pilgrimage route linking northern Europe with Rome that crossed Tuscany. The constant flow of pilgrims, merchants and travellers made Siena a strategic point for trade, lodging and finance, sowing the seeds of its later splendour.
Between the 12th and 14th centuries, Siena lived its golden age as an independent republic, one of the most prosperous and powerful city-states in Italy. Its wealth rested on two pillars: trade, thanks to its position on the Via Francigena, and above all finance. Sienese bankers were among the most important in Europe and handled the papacy's finances; the Bonsignori family, with its Gran Tavola, became one of the largest banking companies on the continent. Centuries later, in 1472, the Monte dei Paschi di Siena was founded; it is still in business and is considered the oldest operating bank in the world.
That economic power inevitably clashed with that of its neighbour Florence, barely a few dozen kilometres away. The two cities were bitter rivals for centuries, and were also on opposite sides of the great conflict of the age: Siena tended to line up with the Ghibellines (backers of the Emperor), while Florence was Guelph (backing the Pope). The rivalry reached its most glorious point for Siena on 4 September 1260, at the battle of Montaperti, where the Sienese army, with Ghibelline support, inflicted a crushing defeat on the Florentines. That victory, remembered with pride for centuries (Dante even mentions it in the Divine Comedy), marked the peak of Sienese military power.
The rivalry was not only political and military but also artistic and architectural: both cities competed to have the largest cathedral, the tallest tower, the most brilliant artists. That constant emulation was one of the engines of the extraordinary cultural flowering both cities would see in the following centuries.
Siena's most brilliant period coincided with the so-called Government of the Nine (il Governo dei Nove), a merchant oligarchy that ran the republic between 1287 and 1355. Made up of nine magistrates chosen from the commercial and banking middle class (excluding the old nobility and the common people), this government brought decades of relative stability and prosperity, and undertook a programme of building and art that gave Siena the shape it still has today.
Much of the city's visible splendour is down to the Nine: the design of the Piazza del Campo with its characteristic shell shape divided into nine sectors (recalling the government itself), the building of the Palazzo Pubblico and the Torre del Mangia, the planning rules requiring harmonious façades and the ambitious project of the Duomo Nuovo, the gigantic cathedral meant to surpass all others. It was a time when civic pride and the idea of 'good government' were set down in stone and in paint.
In that climate the Sienese school of painting flourished, one of the high points of European Gothic. Duccio di Buoninsegna renewed painting with his monumental Maestà; Simone Martini dazzled with his refined elegance; and the brothers Pietro and Ambrogio Lorenzetti took painting to new heights of realism and storytelling. The cycle of the Allegory of Good and Bad Government that Ambrogio Lorenzetti painted in the Palazzo Pubblico is the visual manifesto of that political ideal: one of the first great secular works in Western painting, showing the fruits of governing justly against the disasters of tyranny.
Siena's splendour broke abruptly in 1348, when the Black Death, the most devastating pandemic in European history, swept the city. Siena is estimated to have lost an enormous share of its population in a few months — according to the sources, more than half its inhabitants — a demographic and economic catastrophe the republic never fully recovered from. The epidemic not only killed a huge part of the population but also disrupted trade, banking and social life, and cut short projects such as the enormous Duomo Nuovo, whose construction was halted for ever (hence the unfinished façade of the Facciatone).
One of the great chroniclers of the plague in Siena was Agnolo di Tura, nicknamed 'the Fat', who left a harrowing account: he told how he buried his five children with his own hands and described mass graves and an end-of-the-world silence. The blow also contributed to the fall of the Government of the Nine, which collapsed in 1355, giving way to decades of political instability, internal factional struggles and successive governments that would never recover the earlier vigour.
From then on, Siena entered a long relative decline against Florence, which was establishing itself as Tuscany's great power. The city kept its independence and its pride for two more centuries, but its age of maximum power was behind it. That interruption of growth had, however, an unexpected and fortunate consequence: with development halted, Siena kept its medieval appearance almost intact, without the great Renaissance and Baroque transformations that remade other cities.
The end of Sienese independence came in the 16th century, amid the great wars between the imperial Spain of Charles V and Philip II and the Kingdom of France, which turned Italy into a battlefield. Siena, which had sought French support to hold out, was besieged by imperial and Florentine troops. After a long, gruelling siege, the city surrendered in 1555, exhausted by hunger. A group of die-hards held out for a few more years in Montalcino (the 'Republic of Siena repaired to Montalcino'), but the cause was lost.
In 1559, under the treaty of Cateau-Cambrésis and later agreements, the territory of Siena passed to Cosimo I de' Medici, duke of Florence, and was absorbed into what would shortly become the Grand Duchy of Tuscany. So the old rival finally fell under Florentine rule, closing centuries of rivalry. Under the Medici and, later, the Habsburg-Lorraines, Siena became a provincial city, quiet and somewhat removed from great events.
Paradoxically, that loss of prominence was its great stroke of luck in heritage terms. No longer a thriving capital, Siena saw hardly any of the great urban reforms that transformed other cities in the following centuries; it was, in a way, frozen in its 14th-century medieval form. That is why it is today one of the best-preserved Gothic urban ensembles in Europe. That exceptional authenticity was recognised in 1995, when Unesco inscribed the historic centre of Siena on the World Heritage list, valuing it as a work of urban art that has stayed faithful to its appearance of the 12th to 15th centuries. Today, medieval life also lives on in the contrade and the Palio, which keep the spirit of the old republic alive.
Siena's identity cannot be understood without the contrade and the Palio, a living tradition rooted in the Middle Ages that still sets the city's pulse. The contrade are Siena's historic districts: today there are seventeen, each with its name, its symbol (an animal or a figure: the Goose, the Tower, the Wave, the Snail, the Eagle, the Panther...), its colours, its church, its museum, its own baptismal fountain and a fierce sense of belonging passed down from one generation to the next. Originally they were groupings that organised defence, festivities and, by tradition, the old military companies of the republic.
The Palio, the horse race that pits the contrade against each other in the Piazza del Campo, has precursors going back to medieval and Renaissance games and contests; in its modern form, with horses circling the square, it took shape around the 17th century. It is run twice a year, on 2 July (Palio di Provenzano) and 16 August (Palio dell'Assunta, dedicated to the Virgin of the Assumption, the city's patron). Ten contrade compete in each race, in a short, dizzying contest that is nonetheless the culmination of a whole year of preparation, rivalries, alliances and rituals.
The extraordinary thing about the Palio is that it is not a tourist re-enactment but a genuine passion for the Sienese, who feel belonging to their contrada as something almost sacred. Baptisms at the contrada fountain, huge dinners in the streets, flags twirled with skill, songs and tears: all of it keeps alive a form of community inherited from medieval Siena. That is why visiting Siena means, in many senses, looking into a Middle Ages that has not entirely gone but still beats in its streets, its squares and its people.