The History of Escorting in Milan: From Ancient Roots to Modern Times

When you think of Milan, you picture fashion runways, luxury boutiques, and espresso bars buzzing with conversation. But beneath the polished surface lies a quieter, older story-one that stretches back centuries. The presence of escort services in Milan isn’t a modern invention born from the internet or globalization. It’s a thread woven into the city’s social fabric since Roman times.

Origins in the Roman Empire

Milan, known as Mediolanum in antiquity, was one of the most important cities in the Western Roman Empire. By the 3rd century AD, it was a political and economic hub, drawing merchants, soldiers, and officials from across the empire. With them came demand for companionship beyond marriage or family ties.

Archaeological finds from Roman-era Milan include inscriptions on tombstones and graffiti in public baths that reference women known as meretrices-a term that covered everything from street-level sex workers to high-status courtesans who advised politicians and hosted intellectual salons. These women weren’t just selling physical intimacy; they offered conversation, cultural refinement, and social access. One such courtesan, documented in a fragmentary inscription from 218 AD, was praised for her poetry and ability to navigate elite circles.

The Roman legal system tolerated these roles as long as they remained outside the bounds of formal marriage. This separation-between respectable women and those in the sex trade-became a template that would echo through Milan’s history for over a millennium.

The Middle Ages: Hidden in Plain Sight

After the fall of Rome, Milan became a battleground for Lombard dukes, Holy Roman emperors, and later, the powerful Visconti and Sforza families. The Church grew stronger, and public morality became tightly controlled. Officially, prostitution was condemned. But in practice, it was managed.

By the 14th century, Milan had designated red-light districts near the city gates-especially around Porta Ticinese and Porta Romana-where brothels operated under municipal licenses. The city collected taxes from these establishments, treating them like any other business. Records from 1397 show that the city council fined a brothel owner for letting clients enter after curfew, not for the act of prostitution itself.

Women working in these spaces were often widows, former servants, or immigrants with few options. Some became well-known figures. One woman, Lucrezia da Pavia, was rumored to have been the secret lover of a Sforza duke and later ran a discreet salon where poets, painters, and diplomats gathered. Her name never appeared in official records, but her influence did.

18th and 19th Centuries: The Rise of the Courtesan Class

By the 1700s, Milan was a center of Enlightenment thought and artistic revival. The aristocracy, now less tied to land and more to urban wealth, sought companionship that matched their intellectual ambitions. The traditional courtesan evolved into something new: a woman of education, style, and discretion.

These women lived in elegant apartments near the Brera district, often funded by wealthy patrons who provided them with art collections, fine clothing, and access to private theaters. Unlike their predecessors, they didn’t advertise openly. Their services were arranged through trusted intermediaries-often older women known as madamas-who vetted clients and maintained secrecy.

One of the most famous was Isabella Riva, who hosted weekly gatherings for composers, including Giuseppe Verdi, who reportedly sketched early drafts of La Traviata during her soirées. The opera, about a courtesan who sacrifices love for honor, became a cultural touchstone. Its success didn’t condemn the lifestyle-it romanticized it.

20th Century: War, Fascism, and Underground Networks

The 1920s and 30s brought Mussolini’s regime, which officially banned prostitution but intensified surveillance. Police kept lists of known sex workers, and women were often forced into state-run rehabilitation centers. Yet demand never disappeared.

During World War II, Milan became a transit point for soldiers, spies, and refugees. The black market thrived, and so did informal networks of companionship. Women who had lost husbands or families turned to escorting not just for survival, but for protection. Allied officers stationed in the city after 1945 brought new patterns: American GIs sought local guides who could navigate postwar Milan’s ruins-and its hidden pleasures.

By the 1960s, as Italy’s economy boomed and tourism grew, escorting began to shift from private homes to hotels and nightclubs. The rise of the automobile and improved communication meant clients could reach escorts more easily. The term escorta started appearing in classified ads in local newspapers, discreetly listed under "companion services" or "tourist assistance."

Modern Era: Digital Transformation and Legal Ambiguity

Italy has never legalized prostitution. But it also doesn’t criminalize selling sex-only pimping, trafficking, and public solicitation. This legal gray zone created space for escort services to adapt.

By the early 2000s, Milan’s escort scene moved online. Websites appeared with profiles, photos, and availability calendars. Many women operated independently, using platforms similar to those used by freelance photographers or translators. They set their own rates, chose their clients, and worked from rented apartments or hotel rooms.

Unlike in cities like Amsterdam or Berlin, there are no licensed brothels in Milan. That means there’s no official oversight. But it also means there’s no stigma attached to the profession in the same way. Many women in Milan’s escort industry today are university graduates, multilingual, and work part-time while pursuing other careers. Some are students. Others are expats from Eastern Europe, Latin America, or Southeast Asia who see the work as a way to support families back home.

Police raids do happen, but they target human traffickers-not independent workers. In 2022, a major operation in the Porta Venezia area arrested three men accused of exploiting foreign women, but no escorts were charged. The city’s stance is clear: if you’re not forcing anyone, you’re not the target.

What It’s Like Today

Today, if you walk through Brera after dark, you won’t see women standing on corners. You might see a woman in a tailored coat stepping into a taxi with a man who looks like a banker. Or a young woman with a laptop in a coffee shop near Navigli, checking messages on a burner phone.

The modern escort in Milan doesn’t need to be visible. She’s a service provider, not a spectacle. Clients come from all walks of life: businessmen on short trips, lonely expats, even married men seeking emotional connection without commitment. The services offered range from dinner and conversation to overnight stays. Rates vary from €150 to €800, depending on experience, language skills, and location.

There’s no official data on how many women work in this space, but estimates from local NGOs suggest between 1,200 and 2,000 women operate independently in the city. Many use encrypted apps, avoid social media, and never disclose their real names. Some have built loyal client bases over years.

Why Milan? The City’s Unique Appeal

Why has Milan become such a persistent center for this industry? Partly because of its global status. It’s one of the world’s top business capitals, with over 150 international companies headquartered there. Every week, thousands of business travelers arrive-many alone, many under pressure, many looking for comfort.

It’s also a city of contrasts. You can have lunch at a Michelin-starred restaurant and then walk five blocks to a quiet apartment where a woman offers quiet companionship. There’s no judgment in the air-just efficiency. Milaners are practical. They don’t romanticize or demonize. They accept what exists.

The city’s architecture, too, plays a role. Narrow alleyways, historic buildings with hidden entrances, and discreet hotel lobbies make it easy to come and go unnoticed. Unlike Rome or Venice, where tourism is visible and controlled, Milan lets people disappear into its rhythm.

Myths and Misconceptions

There are a lot of myths about escorting in Milan.

One myth is that it’s dangerous. For independent workers, it’s often safer than other service jobs. They screen clients carefully, meet in public first, and carry panic buttons. Most incidents involve organized crime-not individual escorts.

Another myth is that all escorts are trafficked. That’s simply untrue. Most work voluntarily, often with support networks of other women who share safety tips, legal advice, and emotional support. Several online forums run by current and former escorts in Milan offer resources on contracts, client vetting, and mental health.

And then there’s the idea that it’s a dying industry. It’s not. In fact, demand has grown since the pandemic. With remote work and digital nomadism on the rise, more people are spending extended time in Milan without social ties. They’re seeking connection-and they’re willing to pay for it.

The Future: Regulation or Disappearance?

Italy has debated legalizing prostitution for decades. Each time, the Church, feminist groups, and law enforcement clash. No consensus has formed.

But change is happening quietly. In 2024, Milan’s city council passed a non-binding resolution encouraging the development of harm-reduction programs for sex workers. It didn’t legalize anything-but it did fund free health screenings, legal consultations, and language classes.

Some escorts are now registering as freelance workers with the Italian tax office. They pay VAT, file income reports, and even receive pensions. It’s not full recognition-but it’s progress.

The future of escorting in Milan won’t be decided by laws. It’ll be shaped by culture. And Milan, as always, moves at its own pace.