A new tour in Philadelphia is offering visitors a glimpse into the city’s Prohibition-era underworld. The Philly Mob Tour, organized by Founding Footsteps, takes participants through the streets of Philadelphia, exploring stories of mob bosses, bootleggers and law enforcement crackdowns that shaped the city from the 1920s to today.
Tim McAleer, founder of Founding Footsteps, launched the tour as part of his company’s commitment to engaging local residents as well as tourists.
“What else can we do towards locals? That’s how my company started,” McAleer explained. “I left teaching almost 15 years ago, and I took a summer job as a double-decker tour guide. I fell in love with it immediately. After three years, we started this company, and locals are what have really been the thing that has taken us to a level I never could have really imagined.”
The new mob tour delves into Philadelphia’s history of drinking and bootlegging during Prohibition. It highlights the city’s early brewing traditions, the great number of taverns, and the rise of speakeasies, which exceeded 5,000 by the mid-1920s. At one point, Philadelphia had more than 1,200 illegal bars operating in South Philly alone, which created a reputation for the city as a bootlegging hub.
Guests on the tour hear stories about the infamous Bear brothers and their influence on city politics, which ultimately led to General Smedley Butler’s appointment as Director of Public Safety. Butler’s aggressive reforms resulted in thousands of speakeasies being shut down. The tour also stops at the Italian Market, where participants learn about Antonio Palumbo, an influential figure who helped Italian immigrants establish businesses and grow Philadelphia’s Italian community.
One of the hosts on the tour bus is George Martorano, who knows a bit about South Philadelphia’s mob history from up close. His father was mob boss Angelo Bruno’s personal driver, and Martorano himself received a life sentence without parole for drug charges, in 1984.
He spent 32 years in prison. While there, he found ways to contribute positively. He wrote several books, developed educational programs for his fellow inmates and eventually helped over 8,000 of them to earn degrees.
“For me, to spend the day in this trolley telling stories with great people is a pleasure, and hopefully we will do more,” Martorano told the tour-goers.
Victoria and Marc Gallagher, participants of the tour, described what drew them to the experience. “We definitely gravitate toward darker, more morbid themes — that’s the kind of stuff we watch at home. We wanted to try something different this time, outdoors. We came across the tour through Instagram and we are enjoying it very much.”
Notable stops include the Benjamin Franklin Hotel, the 21 Club, the Hotel Sylvania and the Franklin Mortgage and Investment Company, each tied to key figures and events from the Prohibition era. The tour is accompanied by live jazz music from Tubey Frank, a Philadelphia-based singer and songwriter.
The Philly Mob Tour features graphic and unsettling content, and is limited to adults (21 years and older). It is BYOB, and tickets are available now at FoundingFootsteps.com.