Did You Know? Italy

Imagine two wealthy Tuscan cities, separated by roughly 50 miles, competing for territory, trade, political influence, and prestige.

That was medieval Tuscany. Florence and Siena became fierce rivals during the Middle Ages, and their rivalry was about much more than simply being neighboring cities.

Siena grew wealthy through banking, trade, and its position along the Via Francigena, an important pilgrimage and trade route connecting northern Europe with Rome. Florence, meanwhile, was becoming a major center of commerce and manufacturing.

Both cities wanted influence over Tuscany. Their political differences added fuel to the rivalry. Siena generally supported the Ghibelline cause, associated with the Holy Roman Emperor, while Florence became strongly associated with the Guelphs and the papacy. The conflict eventually produced one of the most famous battles in medieval Italian history: the Battle of Montaperti, fought on September 4, 1260.

The battle took place along the Arbia River outside of Siena. Florence heavily outnumbered the Sienese forces. Knowing they lacked the numbers for a direct assault, they divided their forces. They launched an initial assault at the center of the Florentine forces before hitting the flanks. Florentine forces were battling more than just the Sienese army. They faced betrayal from within. During a critical moment, Bocca degli Abati, a Florentine noble secretly loyal to the Ghibellines, rode up to the Florentine standard-bearer and cut off his hand. The falling flag triggered panic and confusion among the Guelph ranks. Their lines collapsed, and as they retreated, the Sienese forces turned the battlefield into a slaughter so intense that Dante Alighieri later described it in the Inferno as the carnage that “dyed the Arbia red.”

The victory temporarily made Siena the dominant military power in Tuscany. After the defeat, exiles led by Farinata degli Uberti, re-entered Florence and established control. Following the victory, Ghibelline leaders at the Council of Empoli proposed razing Florence to the ground. Farinata degli Uberti stood alone in opposition and defended the city from destruction.

Dante later remembered the battle in his Divine Comedy. In the Inferno, he encounters souls associated with the political and military world of his time, including Farinata degli Uberti (Inferno, Canto X) and the traitor Bocca degli Abati (Inferno, Canto XXXII).

But medieval rivalries rarely stayed settled.

Florence eventually recovered. In 1269, the Florentines defeated Siena at the Battle of Colle Val d’Elsa. The Sienese forces led by Provenzano Salvani marched on Colle Val d’Elsa to suppress the Guelph stronghold and secure trade routes along the Via Francigena. Expecting little resistance, a coordinated surprise attack was launched by the Guelphs, causing chaos. Salvani, the supreme leader of Siena who had orchestrated the victory at Montaperti, was unhorsed, captured, and decapitated on the field by his enemy Regolino Tolomei. Seeing his head raised on a lance, the Sienese army panicked and fled.

The devastating defeat crippled the Sienese military and forced Siena to accept a pro-Guelph government, ending the era of Ghibelline supremacy across Tuscany.

The rivalry also found its way into architecture and civic pride. Florence built its enormous cathedral complex. Siena responded with an equally ambitious vision for its cathedral, including plans for an extraordinary expansion that would have transformed it into one of Europe’s largest churches. The project ultimately failed, leaving the unfinished walls that can still be seen today.

Even their public spaces became symbols of civic identity. Siena’s Piazza del Campo became one of Italy’s most remarkable medieval squares, while Florence developed its own extraordinary civic center around Palazzo Vecchio.

Their rivalry helped create two very different — but equally fascinating — visions of medieval Tuscany. And perhaps the greatest irony? The competition between Florence and Siena helped produce some of the artistic and architectural treasures that make Tuscany famous today.

If you could spend a day in medieval Tuscany, would you choose Florence or Siena? What would you want to see?

Related Articles:

• Dante Alighieri
• Campanile di Giotto
• Siena’s Duomo

Join us every day as we explore a fascinating fact, untold story, or remarkable piece of Italy’s history and culture. Whether your family came from Italy, you’ve traveled there, or you dream of visiting one day, this year-long journey is your daily passport to the heart of Italy. You can follow us on Facebook, Instagram or X (formerly Twitter). You can subscribe for free by filling out the form below to get it sent to your email.

Did You Know? Italy

Long before Florence became synonymous with Michelangelo, Leonardo da Vinci, and the Renaissance, it was already one of the most important cities in medieval Italy.

Located along the Arno River, Florence began the Middle Ages as a relatively modest city compared with some of Italy’s ancient Roman centers. But during the 11th and 12th centuries, Florence began to grow rapidly. Trade, banking, textiles, and craftsmanship transformed the city into a wealthy and increasingly powerful commune.

One of Florence’s greatest economic advantages was its wool industry. Florentine merchants imported raw wool, had it processed and dyed by local craftsmen, and then sold the finished cloth throughout Europe. The city’s merchants became so influential that Florence developed sophisticated financial institutions and eventually became one of medieval Europe’s major banking centers.

And then there was the money. Florence introduced the famous florin, or fiorino d’oro, in 1252. The gold coin quickly became one of Europe’s most trusted currencies. Its reputation spread far beyond Tuscany and became a symbol of Florence’s growing economic influence.

Merchant families like the Bardi, Peruzzi, and later the Medici pioneered double-entry bookkeeping, bills of exchange, and international branch banking, funding European monarchs, popes, and noble dynasties.

But wealth brought political competition. Florence was divided by powerful families and factions, most famously the Guelphs and Ghibellines. The Guelphs generally supported the papacy, while the Ghibellines tended to support the Holy Roman Emperor. Their rivalry could turn violent, and Florence’s political history became a complicated story of alliances, exiles, betrayals, and changing power.

Florence was predominantly a Guelph stronghold, famously defeating imperial-backed Arezzo at the Battle of Campaldino (1289). After driving out the Ghibellines, the Florentine Guelphs fractured internally into Black Guelphs and White Guelphs. Dante Alighieri himself was caught up in these political struggles. He was born in Florence around 1265 and became involved in Florentine politics. When the radical “Blacks” eventually seized power with papal support, Dante was permanently exiled from the city in 1302.

The Florence we associate with the Renaissance did not suddenly appear in the 1400s. Its foundations had been laid centuries earlier through commerce, banking, political institutions, and an increasingly wealthy urban population.

The Renaissance may have made Florence famous. But medieval Florence had already built the stage.

If you could visit medieval Florence before the Renaissance, what would you want to see — the markets, workshops, churches, or political life?

Related Articles:

• Dante Alighieri
• Campanile di Giotto
• Tree of Life

Join us every day as we explore a fascinating fact, untold story, or remarkable piece of Italy’s history and culture. Whether your family came from Italy, you’ve traveled there, or you dream of visiting one day, this year-long journey is your daily passport to the heart of Italy. You can follow us on Facebook, Instagram or X (formerly Twitter). You can subscribe for free by filling out the form below to get it sent to your email.

Did You Know? Italy

Long before tourists traveled to Pisa to take pictures holding up its famous leaning tower, the city was a major military and commercial power.

During the Middle Ages, Pisa was one of Italy’s great maritime republics. Its location on the western coast of Tuscany gave it access to the Mediterranean, allowing its merchants and ships to travel throughout the region.

Pisa became particularly powerful between the 11th and 13th centuries. Its fleets fought Muslim forces in the western Mediterranean and helped expand Pisa’s commercial influence.

Pisan merchants established trading connections across the Mediterranean and gained access to important ports. The city’s wealth was reflected in its architecture. The famous Piazza dei Miracoli, or Square of Miracles, eventually became home to the cathedral, baptistery, cemetery, and the bell tower that would become known as the Leaning Tower of Pisa. The cathedral complex was a statement of Pisa’s wealth and confidence.

But Pisa’s greatest rival wasn’t a distant kingdom. It was another Italian maritime republic: Genoa. The two powers fought repeatedly for control of Mediterranean trade.

On August 6, 1284, near the islet of Meloria off the Tuscan coast, the largest naval engagement of the Middle Ages took place at the Battle of Meloria. The battle was the culmination of two centuries of intense commercial and political friction between Pisa and Genoa. Pisa assembled a fleet of 72 galleys commanded by Podestà Alberto Morosini and Count Ugolino della Gherardesca. Genoa countered with a fleet of 88 galleys split into two lines. Oberto Doria engaged the Pisan fleet directly with 58 galleys, while Admiral Benedetto Zaccaria kept 30 galleys hidden beyond the horizon. The hidden fleet ambushed the exposed Pisan flank, shattering their line and causing extensive human and military losses.

The defeat marked a major turning point. Pisa’s maritime power declined, while Genoa’s influence expanded. This opened the door for Tuscan rival Florence to lay siege to Pisa and taking them under its control.

Its days as an independent maritime power were over. Yet the city never lost its cultural importance. The monuments built during Pisa’s prosperous medieval period remain among Italy’s most recognizable landmarks.

The story of Pisa reminds us that the medieval Mediterranean was not dominated only by kings and emperors. Italian cities themselves could build fleets, wage wars, establish trading networks, and compete for control of international commerce.

Before the Leaning Tower became a tourist icon, Pisa was a maritime powerhouse.

Were you surprised to learn that Pisa was once a major naval power?

Related Articles:

• Dante Alighieri
• Leaning Tower of Pisa
• Palio di San Ranieri

Join us every day as we explore a fascinating fact, untold story, or remarkable piece of Italy’s history and culture. Whether your family came from Italy, you’ve traveled there, or you dream of visiting one day, this year-long journey is your daily passport to the heart of Italy. You can follow us on Facebook, Instagram or X (formerly Twitter). You can subscribe for free by filling out the form below to get it sent to your email.

Did You Know? Italy

When people think about medieval Italy’s great maritime powers, Venice usually gets the spotlight. But across the Italian peninsula was another powerful maritime republic that could match Venice ship for ship: Genoa.

Located on the Ligurian coast, Genoa grew into a major Mediterranean trading power. Its merchants established commercial networks stretching across Europe, North Africa, and the eastern Mediterranean. Genoese ships carried valuable goods, while Genoese merchants established trading communities and colonies in strategic ports.

But Genoa and Venice were competitors—and sometimes bitter enemies. The rivalry became particularly intense during the 13th and 14th centuries. The two republics fought several conflicts over access to trade routes and commercial privileges.

One of the most important confrontations came during the War of Chioggia, fought between 1378 and 1381. Genoa came surprisingly close to defeating Venice. Genoese forces seized the island of Chioggia at the entrance to the Venetian lagoon. Venice launched a desperate counter-siege, blockading the Genoese fleet inside the lagoon and forcing their surrender.

The war permanently altered the trajectory of both states. Venice maintained its independence and remained the preeminent trade empire in the East. Genoa pivoted to banking and remained a major financial and commercial center. Its banking families became extremely wealthy, and Genoese financiers eventually played important roles in European finance. The city’s influence extended far beyond Italy.

Genoese explorers and merchants traveled throughout the Mediterranean and beyond. One of the city’s most famous sons—or at least its most famous adopted historical figure—was Christopher Columbus, traditionally identified as Genoese.

Today, Genoa’s historic center still contains reminders of its extraordinary maritime past. Its massive harbor, palaces, churches, and narrow medieval streets tell the story of a city that once competed with Venice for control of Mediterranean commerce.

Venice may have become the more famous maritime republic, but Genoa was never simply Venice’s sidekick. For centuries, the two were locked in one of medieval Europe’s greatest commercial rivalries.

If you could visit one medieval maritime republic, would you choose Venice or Genoa?

Related Articles:

• Dante Alighieri
• The Crossbowmen of Genoa Were Medieval Europe’s Elite
• Venice Was Built on Water

Join us every day as we explore a fascinating fact, untold story, or remarkable piece of Italy’s history and culture. Whether your family came from Italy, you’ve traveled there, or you dream of visiting one day, this year-long journey is your daily passport to the heart of Italy. You can follow us on Facebook, Instagram or X (formerly Twitter). You can subscribe for free by filling out the form below to get it sent to your email.

Did You Know? Italy

One of the most famous cities in the world appears to float on water. Venice was built across a collection of islands in a lagoon along Italy’s northeastern coast. But why would anyone choose such a difficult place to build a city?

The story begins during the turbulent centuries following the decline of the Western Roman Empire. People fleeing invasions and warfare sought refuge in the islands and marshes of the Venetian Lagoon. The water provided a natural defense. Over time, temporary settlements became permanent communities. Builders harvested millions of tree trunks (primarily alder, larch, and oak) from forests across Slovenia, Croatia, and Northern Italy. They drove these logs vertically into the muddy lagoon floor until reaching a dense layer of hard clay called caranto. The timbers are completely submerged in the mud, which depletes it of oxygen and preserves it from decay and rot. Over centuries, the wood petrified into a stone-like strength. The tops of the driven piles were leveled off, covered with horizontal timber planks, and layered with waterproof Istrian limestone blocks.

Eventually, a remarkable city emerged. Venice started harvesting and trading salt from its lagoon salt pans. Using salt as leverage, Venetian merchants secured exclusive trading rights along northern Italian rivers, establishing a monopoly that forced neighboring cities to trade through Venice. They maintained ties with the Byzantine Empire and helped defend Byzantium from Norman invaders. In appreciation, Emperor Alexios I Komnenos issued a Golden Bull granting merchants tax-free trading rights across the entire Byzantine Empire. This gave Venice a massive commercial advantage over rival Italian maritime republics like Genoa and Pisa.

Venice became one of the great maritime powers of medieval Europe. Its location allowed Venetian merchants to connect Europe with the Byzantine Empire and the wider Mediterranean world. Ships carried spices, silk, precious metals, textiles, and countless other goods. Venice developed a powerful merchant class and an unusual political system led by the Doge. Its wealth helped finance magnificent churches, palaces, ships, and works of art.

Today, Venice remains one of Italy’s most recognizable cities. Its canals, bridges, palaces, and churches are the product of centuries of engineering, commerce, warfare, and ambition. Venice didn’t simply grow beside the water. Venice conquered the water—and built a city upon it.

Would you have had the courage to build a city in a lagoon?

Related Articles:

• Festa della Madonna della Salute
• Songs from Veneto
• Sposalizio del Mare

Join us every day as we explore a fascinating fact, untold story, or remarkable piece of Italy’s history and culture. Whether your family came from Italy, you’ve traveled there, or you dream of visiting one day, this year-long journey is your daily passport to the heart of Italy. You can follow us on Facebook, Instagram or X (formerly Twitter). You can subscribe for free by filling out the form below to get it sent to your email.

Did You Know? Italy

High on a hill in the Tuscan countryside sits a town that looks almost frozen in time. San Gimignano is famous for its stone towers, earning it the nickname “the Medieval Manhattan” due to its striking skyline of towering stone house-towers (case-torri).

During the Middle Ages, San Gimignano was an important stop along the Via Francigena, a major pilgrimage route connecting northern Europe with Rome. Pilgrims, merchants, and travelers passed through the town, bringing wealth and opportunity. As San Gimignano became prosperous, powerful families began constructing tall towers as symbols of their wealth and influence.

At one point, the town had around 70 towers. Competition between rival families was intense. They constantly competed to build the highest tower as a sign of power and prestige. Towers weren’t just homes—they were statements.

The Black Death in 1348 killed over half of the population. Over time, political struggles and changing economic conditions reduced San Gimignano’s importance. Florence gained increasing influence over the region, halting new construction and unintentionally preserving its 14th-century architectural layout virtually intact.

While other Italian cities modernized, rebuilt, or demolished medieval structures, San Gimignano retained much of its medieval character. Today, 14 towers remain. The tallest, Torre Grossa (built in 1311), stands at 54 meters (177 ft). In 1990 the town was designated a UNESCO World Heritage Site, recognizing its exceptional preservation.

Walking through the town’s narrow streets can feel like stepping into another century. The towers rise dramatically above terracotta rooftops, while medieval stone buildings surround the central squares.

San Gimignano is also famous for its wine, particularly Vernaccia di San Gimignano, one of Italy’s historic white wines produced locally since the 13th century.

What makes San Gimignano special isn’t just its towers. It’s the fact that those towers tell the story of medieval Italy itself—a world of rival families, wealthy merchants, pilgrimage routes, independent towns, and fierce competition for power.

Have you ever visited San Gimignano—or would it be on your Italian travel bucket list?

Related Articles:

• Dante Alighieri
• Leaning Tower of Pisa
• Songs from Tuscany

Join us every day as we explore a fascinating fact, untold story, or remarkable piece of Italy’s history and culture. Whether your family came from Italy, you’ve traveled there, or you dream of visiting one day, this year-long journey is your daily passport to the heart of Italy. You can follow us on Facebook, Instagram or X (formerly Twitter). You can subscribe for free by filling out the form below to get it sent to your email.

Did You Know? Italy

If you look at medieval Italian towns, especially in Tuscany and Emilia-Romagna, you’ll notice something unusual: towers everywhere.

These weren’t simply medieval skyscrapers. During the Middle Ages, towers symbolized wealth, power, protection, and family prestige. In cities such as Bologna, Florence, and San Gimignano, wealthy families constructed tall towers attached to or near their homes. Some served as private urban fortresses, status symbols, and defensive strongholds during a period of intense political instability. The higher the tower, the more impressive the statement.

In medieval Italy, powerful families often competed with one another for political influence. Their towers became highly visible symbols of that rivalry. As the population grew within city walls that already had small urban footprints, the only way to expand was building upward.

Bologna was once famous for having hundreds of towers. Many were eventually demolished, collapsed, or incorporated into later buildings. Today, only a fraction survive, including the famous Two Towers (Le Due Torri), the Asinelli and Garisenda. Built in the early 12th century by rival Ghibelline families, they serve as the ultimate surviving example of medieval architectural competition. The Asinelli rises to a height of 97.2 meters (319 feet) and is the tallest original medieval tower in Bologna. The Garisenda originally stood at 60 meters (197 feet), but it was built on unstable ground, causing it to lean. The structure was reduced to its current height of 48 meters (157 feet). This is Bologna’s version, rivaling the Leaning Tower of Pisa.

San Gimignano in Tuscany offers perhaps the most famous surviving example of this medieval skyline. The town once had dozens of towers belonging to rival families. Today, 14 medieval towers still stand, giving San Gimignano its distinctive appearance.

The towers also had practical purposes. Their height provided excellent views over the surrounding countryside. Thick walls could make them defensible, and their upper floors could serve as living or storage spaces. There was another reason to build them tall: competition. Imagine being a wealthy medieval family and seeing your rival’s tower rising above your neighborhood. Building your own tower higher could become a very literal architectural arms race.

Eventually, city governments began restricting the construction of towers because of concerns about warfare, instability, and the dominance of individual families. The towers that remain today are more than beautiful landmarks. They are stone reminders of a time when Italy wasn’t governed by a single national government. Instead, cities and families competed for power—and sometimes they measured that power in feet of stone.

If you lived in medieval Italy, would you want your family to have its own tower?

Related Articles:

• Campanile di Giotto
• Dante Alighieri
• Niccolò Machiavelli

Join us every day as we explore a fascinating fact, untold story, or remarkable piece of Italy’s history and culture. Whether your family came from Italy, you’ve traveled there, or you dream of visiting one day, this year-long journey is your daily passport to the heart of Italy. You can follow us on Facebook, Instagram or X (formerly Twitter). You can subscribe for free by filling out the form below to get it sent to your email.

Did You Know? Italy

During the Middle Ages, the Italian maritime republic of Genoa was famous for ships, merchants—and some of Europe’s most feared soldiers.

The Genoese crossbowmen were professional soldiers renowned throughout the Mediterranean for their discipline, powerful steel-strung crossbows, and formidable battlefield defense. The crossbow was a powerful weapon for its time. It could be easier to use effectively than a traditional longbow and could penetrate armor at relatively short distances.

Equipped with composite or steel crossbows, these marksmen unleashed heavy iron bolts (quadrells) capable of shattering mail and early plate armor at close range. To safely reload their slow-cranking weapons, crossbowmen ducked behind a pavise—a massive, flat wooden shield set up on the battlefield. For defense and melee fighting, each man wore a steel helmet and a padded gambeson or mail shirt, and carried a short sword or dagger for hand-to-hand combat.

Genoa’s crossbowmen became so respected that foreign rulers hired them for military campaigns. They fought in conflicts throughout Italy and across Europe.

Their reputation became particularly significant during the Hundred Years’ War, when Genoese crossbowmen were employed by the French. At the Battle of Crécy in 1346, Genoese crossbowmen fought alongside the French army against the English. The battle ended disastrously for the French, and the crossbowmen suffered heavy losses.

One problem was that the Genoese troops reportedly arrived without adequate protection from the English longbowmen, while their pavises—large shields normally used to protect crossbowmen while they reloaded—were not immediately available. Sudden rain softened their hemp strings, reducing the effectiveness of the arrow whereas the English longbowmen unstrung their bows to keep them dry.

Despite the defeat, the reputation of Genoese crossbowmen survived. Their story highlights the international nature of medieval warfare. A soldier from Genoa could fight in France, Italy, the Mediterranean, or somewhere else entirely.

Genoa’s wealth as a maritime trading power helped support this military tradition. The city was one of the great commercial republics of medieval Europe, competing fiercely with Venice for control of Mediterranean trade. Its merchants, ships, colonies, and soldiers helped make Genoa a major power.

Today, Genoa is often celebrated for its maritime history, Christopher Columbus, and its magnificent old city. But during the Middle Ages, you might also have heard another description: Genoa was home to some of Europe’s most dangerous crossbowmen.

Would you rather face a medieval knight or a Genoese crossbowman?

Related Articles:

• The Battle of Legnano
• Dante Alighieri
• Swiss Guards

Join us every day as we explore a fascinating fact, untold story, or remarkable piece of Italy’s history and culture. Whether your family came from Italy, you’ve traveled there, or you dream of visiting one day, this year-long journey is your daily passport to the heart of Italy. You can follow us on Facebook, Instagram or X (formerly Twitter). You can subscribe for free by filling out the form below to get it sent to your email.

Did You Know? Italy

Before becoming one of the greatest poets in European history, Dante Alighieri was a young Florentine who participated in medieval politics—and even went to war.

In 1289, Florence and its allies fought the forces of Arezzo at the Battle of Campaldino in Tuscany. Dante was present as part of the Florentine forces. He was 24 when he fought in the battle as a feditore (mounted frontline cavalryman) in the Florentine vanguard.

The battle was connected to the complicated political struggle between the Guelphs and Ghibellines. The Florentine Guelphs, were loyal to the papacy, and supported by allied Tuscan communes and French mercenaries under Amerigo di Narbona. The Aretine Ghibellines, who were loyal to the Holy Roman Emperor, were led by Bishop Guglielmino Ubertini and the military commander Bonconte da Montefeltro.

The turning point in the war occurred when the Ghibellines launched a fierce initial cavalry charge that pushed back the Florentine vanguard. However, the Florentines absorbed the shock with heavy infantry shield-walls (pavesi). Corso Donati, commanding the Florentine reserve cavalry, disobeyed orders and charged the exposed Ghibelline flank, breaking their lines and routing their forces.

The Florentine army won a decisive victory. For Dante, the experience would become part of the world that influenced his later writing. He had witnessed medieval warfare firsthand—the chaos, fear, political rivalries, and human consequences. Years later, Dante would transform his experiences of Florence’s turbulent political world into some of the most influential literature ever written.

His masterpiece, The Divine Comedy, would eventually take readers on an extraordinary journey through Hell, Purgatory, and Paradise. His experience at the Battle of Campaldino in 1289 deeply influenced The Divine Comedy, transforming real historical figures from the battlefield into literary symbols of divine justice, repentance, and political tragedy.

In Canto V of Purgatorio Dante vividly describes the death of his battle opponent, Bonconte da Montefeltro, whose body was never recovered after the storm that flooded the Archiano river on the night of the battle. In Canto XII of Inferno Dante references seeing cavalry deployments, charges, and tournaments, drawing directly from his first-hand military service at Campaldino.

Campaldino is therefore more than just another medieval battle. It offers a glimpse into the young man behind the poet. Dante wasn’t born into a peaceful world of books and poetry. He lived in a fiercely political Florence where rival factions fought for power and where citizenship could come with very real dangers. His experiences in politics, exile, and conflict helped shape the worldview that would make him one of Italy’s most important literary figures.

Standing on the battlefield at Campaldino, Dante couldn’t have known that his name would one day become synonymous with Italian literature. But history has a funny way of placing remarkable people in remarkable moments.

Did you know Dante actually participated in a medieval battle?

Related Articles:

• The Battle of Legnano
• Dante Alighieri
• Niccolò Machiavelli

Join us every day as we explore a fascinating fact, untold story, or remarkable piece of Italy’s history and culture. Whether your family came from Italy, you’ve traveled there, or you dream of visiting one day, this year-long journey is your daily passport to the heart of Italy. You can follow us on Facebook, Instagram or X (formerly Twitter). You can subscribe for free by filling out the form below to get it sent to your email.

Did You Know? Italy

During the late Middle Ages and Renaissance, Italy became famous for something unusual: armies that often fought for whoever could pay them. These soldiers were known as condottieri. The word comes from condotta, meaning a contract. Condottieri were professional military commanders who entered contracts with cities, princes, popes, and other rulers. Rather than serving one kingdom for their entire lives, they could negotiate their services.

This might sound strange today, but medieval Italy was divided among powerful city-states and territories that constantly competed with one another. Venice, Florence, Milan, the Papal States, Naples, and smaller states all needed soldiers. Some condottieri became enormously wealthy and powerful.

One of the most famous was Francesco Sforza, who eventually became Duke of Milan. He began his career as a military commander and used his influence to seize political power, establishing the Sforza dynasty. Another famous commander was Bartolomeo Colleoni, who served Venice with distinction. He is famous for introducing field artillery tactics. He is honored with an iconic bronze equestrian statue in Venice.

The condottieri weren’t always the bloodthirsty warriors popular imagination might suggest. Many were highly trained professionals who understood that preserving their troops could be just as important as winning a battle. Medieval warfare could be expensive, and commanders sometimes preferred maneuvering and negotiation to unnecessary casualties.

Their system also created problems. A mercenary commander could switch sides if circumstances changed, and rulers sometimes found themselves at the mercy of powerful military leaders.

The condottieri became an important part of the political landscape of medieval and Renaissance Italy. Their story also demonstrates something essential about Italy’s city-state era: war was often a business, and military power could translate directly into political power.

The reliance on mercenary captains began to crumble when armies from France and Spain invaded Italy, equipped with advanced field artillery and disciplined pike squares. The condottieri proved unable to match the scale and lethality of these foreign armies.

Niccolò Machiavelli fiercely criticized the system in The Prince, arguing that reliance on mercenary forces made Italian states inherently unstable, disloyal, and vulnerable to foreign conquest.

Would you trust an army whose soldiers were fighting under contract?

Related Articles:

• The Battle of Legnano
• Niccolò Machiavelli
• Swiss Guards

Join us every day as we explore a fascinating fact, untold story, or remarkable piece of Italy’s history and culture. Whether your family came from Italy, you’ve traveled there, or you dream of visiting one day, this year-long journey is your daily passport to the heart of Italy. You can follow us on Facebook, Instagram or X (formerly Twitter). You can subscribe for free by filling out the form below to get it sent to your email.