English Italy is famous for historic towns that boast outsized legacies. Many places that today feel like quiet, charming backwaters were once powerhouses of population, trade, or culture. In medieval or ancient times, they stood as giants – only to see their fortunes fade over the centuries. This kind of city – not just in Italy but everywhere in Europe (think of Plovdiv in Bulgaria or Cordoba in Spain) – is often a fantastic hunting ground for history and real estate.
In this article, we explore eight Italy’s fallen superpowers beloved by expats and retirees, where a glorious past still echoes in picturesque streets and piazzas. Each of these towns went from boom to relative bust, offering a fascinating contrast between then and now.
Data visualisation: historical population of the top 10 cities in Italy between 500BCE and today (source: World Population Database, analysis by Magic Towns, refers to metro area).
Venice: From Largest City in Italy to Open-Air Museum
Few people can believe that Venice was the largest Italian city for centuries. Only in the 1800s did the population of Rome catch up with Venice. No city exemplifies rise-and-fall better than Venice. Venice reigned as a wealthy maritime republic and one of Europe’s largest cities. In the year 1000, it had about twice as many inhabitants as Paris. By around 1400, its population exceeded 100,000, making it the most populous city in Italy at the time. As a hub of commerce between East and West, it amassed immense wealth and an empire along the Adriatic, stretching all the way to Crete and Cyprus.
Fast-forward to today, and Venice’s historic center has become a fragile jewel with fewer than 50,000 residents remaining. The city has lost over 120,000 inhabitants since the 1950s. With mass tourism overwhelming daily life, locals warn they feel like “relics in an open museum” as their community dwindles. Yet the canal-laced beauty and cultural riches of Venice endure, drawing visitors and foreign retirees alike.
Amalfi: Medieval Maritime Power Turned Seaside Escape
Today’s Amalfi is a postcard-perfect coastal town (population around 5–6k) perched between mountains and sea. It’s hard to imagine that a millennium ago, Amalfi was a maritime superpower. Around the year 1000, the Duchy of Amalfi likely had 50,000–70,000 residents and was among Italy’s most prosperous cities, dominating Mediterranean trade before Venice or Genoa rose to prominence. As one of the first maritime republics, Amalfi’s ships and merchants were famed far and wide. However, conquest by rival Pisa in 1137 abruptly ended Amalfi’s independence, and the town’s importance declined rapidly thereafter.
Plagues and economic shifts shrank the population to only a few thousand by the 19th century. This steep decline ironically preserved Amalfi’s historic charm. Today it offers an enchanting escape with its Arab-Norman Cathedral, cliffside houses, and lemon groves – a far cry from its days commanding a trade empire. Expats and travelers adore Amalfi for its relaxed pace and beauty, likely unaware that this quiet haven once ruled the waves of the Mediterranean.
Capua: Ancient Italy’s Second City, Now Sleepy and Split
In Roman times, Capua was so significant it was called the “second city” of Italy, rivaled only by Rome itself. Founded around the 6th century BCE, Capua grew fabulously wealthy on fertile Campanian plains – famous for bronze works, perfumes, and a massive amphitheater where gladiators like Spartacus fought. By the 2nd Punic War (218–201 BCE), Capua’s prestige and population were second to none except Rome.
Yet Capua’s fortunes reversed dramatically. After backing the wrong side against Rome, it suffered punitive reprisals, and centuries later was devastated by barbarian invasions. The original ancient city (near modern Santa Maria Capua Vetere) never recovered and was largely abandoned by the Middle Ages. A smaller modern Capua was established nearby, but today it’s a modest provincial town of under 20,000 people. Still, history buffs can explore remarkable remnants of Capua’s glory – notably the Amphitheater of Capua, one of the largest in the Roman world (second only to the Colosseum).
Aquileia & Grado: Roman Metropolis and Its Lagoon Refuge
Located in the quiet Friulian countryside, Aquileia is a tiny village of just a few thousand – but 1,800 years ago it was a thriving Roman metropolis. In the 2nd century CE, Aquileia’s population neared 100,000, ranking it among the largest cities of the Roman Empire. As the Roman Empire’s northeastern bastion, Aquileia was a wealthy trade center at the head of the Adriatic Sea and later a cradle of early Christianity. Its stature made it a target: in 452 CE, Aquileia became the first Italian city sacked by Attila the Hun, an event it would never bounce back from.
Over subsequent centuries, Aquileia dwindled to a rural backwater even as its magnificent basilica and forum fell to ruins. Many survivors fled into the nearby lagoons for safety. One refuge was Grado, a small island town which became the new seat of Aquileia’s patriarch (bishop) by the late 6th century (Grado is in fact nicknamed the First Venice, and had strong ties with Venice under its rule for almost a millennium). Grado has in turn evolved from a sanctuary into a quaint fishing village and spa resort. Today, Aquileia and Grado present a fascinating dual visit: Aquileia offers sprawling Roman ruins and mosaics (a UNESCO World Heritage site) amid pastoral calm, while Grado provides Old World seaside charm. It’s humbling to realize this tranquil corner of northeastern Italy once hosted a metropolis whose population and importance dwarfed many capitals of Europe.
Siracusa (Syracuse): Ancient Supercity to Baroque Gem
Siracusa, on the southeastern coast of Sicily, is a city where past grandeur still attracts large amounts of expats and retirees. Wander its elegant baroque streets now and you’ll find a mid-sized city of about 120,000 people – but in antiquity, Syracuse was a superpower.
Founded by Greek colonists, it grew into the most important city of Magna Graecia, famed for its rich culture and formidable military. By the 5th century BC, Syracuse rivaled Athens in size and might. Cicero himself described it as “the greatest Greek city and the most beautiful of them all”, noting it equaled Athens in the Classical era. At its peak, the wider Syracusan state may have counted roughly 250,000 people, a staggering figure for the time.
Across the centuries, Syracuse saw it all: conflicts with Athens and Carthage, rule under Romans and Byzantines (even serving briefly as the capital of the Byzantine Empire in the 660s), and eventual eclipse by other Sicilian cities like Palermo. Today’s Siracusa wears its layers of history gracefully: the Greek theatre, ancient temple columns, and medieval alleyways of Ortygia island make the past palpable. The entire city is recognized as a UNESCO World Heritage site for its classical and baroque treasures. For expats and retirees, Siracusa offers an attractive blend of historic ambiance with a comfortable modern town – a far cry from its days as a teeming ancient metropolis, yet still proudly bearing the imprint of its illustrious past.
✨ Read our article: “What People Say About Living in Siracusa”
Siena: The Medieval City That Time Froze
Few places capture medieval ambiance like Siena in Tuscany. In the 13th and early 14th centuries, this walled city-state was a wealthy powerhouse of 50,000 people, rivaling Florence in banking, trade, and art. Then came 1348: the Black Death killed up to half of Siena’s population, but unlike other cities, it never bounced back. The plague and later conquest by Florence froze the city in time.
Remarkably, Siena didn’t regain its pre-1348 population until the 20th century. This centuries-long stagnation preserved its Gothic splendor – the grand cathedral remains half-finished since the 1300s, and the cityscape was never remodeled by Renaissance or industrial growth. Today around 54,000 people live in this university town and tourist favorite. The famous Piazza del Campo and Palio horse race tradition exist precisely because tragedy hit the pause button on Siena’s development. Its beauty rests on a haunting irony: a city preserved by catastrophe.
✨ Read our article: “What People Say About Living in Siena”
Cremona – Fiddling Through Rise and Fall
Cremona in Lombardy is famous as the violin-making capital, home of Stradivari and Amati. But around 1300, this prosperous commune was one of Europe’s larger cities with roughly 80,000 inhabitants – remarkably, that’s even more than it had in 2001 (about 69,000). However, war and plagues devastated the city over following centuries; a 17th-century outbreak reduced Cremona to barely 10,000 residents.
By the 1800s, medieval Cremona was just a memory in a quiet provincial town. Today’s population of about 70,000 has nearly returned to its medieval peak. Visitors can admire the 12th-century cathedral and towering Torrazzo, and explore workshops of contemporary luthiers carrying on the violin tradition. It’s a tranquil place with a slow pace – a far cry from the throbbing medieval metropolis it once was. For those looking to retire in a culturally rich but manageable Italian city, Cremona hits the right notes, proving that even after cycles of rise and fall, a city’s soul can sing on.
Crotone – Olympian City Now Off the Beaten Path
On Calabria’s coast, Crotone is a lesser-known town of about 60,000 with rustic beaches and a small historic center. Yet in the 6th and 5th centuries BCE, ancient ‘Kroton‘ was one of the biggest cities in the Greek world. Around 500 BC it boasted 50,000-80,000 inhabitants – rivaling Athens itself.
Kroton was famed for its Olympic champions (including the legendary wrestler Milo) and hosted the philosopher Pythagoras around 530 BC. The city’s armies destroyed neighboring Sybaris in 510 BC, cementing Kroton‘s dominance in the region. But Roman conquest and medieval neglect erased Crotone’s prominence. By the 1800s it was a sleepy fishing village on a malarial coast, only growing again in the 20th century as a small port city.
Today, Crotone sits decidedly off the tourist trail. Intrepid expats value its authentic southern Italian character and low cost of living. Remnants of its Greek past, like the column of Hera Lacinia’s temple, hint at how this humble town was once a thriving metropolis where mathematicians and Olympians walked its streets.
Final thoughts
These eight cities remind us that greatness is never permanent. What once dominated can fade; what seems insignificant today may have ruled centuries ago. This reversal of fortune creates something special – places where you can sip coffee in a quiet piazza that once echoed with the footsteps of emperors, merchants, and philosophers.
For those seeking a home in Italy, these fallen superpowers offer an unexpected gift. Here, history isn’t locked behind museum glass – it’s woven into daily life, visible in every archway and cobblestone. You get the soul of a former capital without the noise and expense of a modern one. In a world obsessed with growth and expansion, these towns teach a different lesson: that there’s profound beauty in what endures after the crowds have gone, in the quiet dignity of places that once commanded empires and now simply invite you to stay awhile.
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