Stories from the Dark Side: Criminals, Gangs & Mafia Tour of NYC

3 hours

Max 20

54 reviews

Step inside the criminal underbelly of New York and learn how it has shaped the city's history and culture. This neighborhood tour, which was developed with the help of retired NYPD officers and detectives, takes you through the stomping grounds of old immigrant gangs, prohibiton mobsters, and bankers who scored big conning the stock market.

  • Sites Visited
  • Wall Street
  • Court district
  • Lower East Side
  • Tenement Buildings
  • Chinatown
  • Little Italy
  • Tour Includes
  • Small group of max 15 people
  • Expert Guide
  • Donut and Coffee

Take a peek into the dark side of New York history

Ever wondered what goes on behind the closed doors of New York City's notorious criminal underworld? For the first time, you don't have to be convicted to get a peek inside. During this excursion with an expert guide (some of whom are retired NYPD officers and detectives), you'll learn the shocking truth of New York’s old immigrant gangs, organized crime rings and modern white collar criminals.

Starting near Wall Street, you'll explore the long history of political corruption in NYC and how it shaped the growth and development of the city. You'll also stop off near the stock exchange to discuss the Wolf of Wall Street and various waves of white collar crime that have often brought the city to its knees.

Next you'll head over to the Lower East Side to immerse yourself in the history of the famous gangs of New York that dominated this area in the 19th century. At the infamous Five Points junction, your guide will tell you about the Irish, Chinese, and Italian gangs that waged bloody warfare for control of the turf.

As you move into Chinatown and Little Italy, the stories become more modern, from Chinese gangs in 70s and 80s; to mafia families that brought Old World crime to New York, with networks of criminality that spanned continents. Those days aren't over yet though. There are rumors that beneath these very streets lurks a whole network of tunnels that lead from Chinatown to the Hudson, allowing free access for smugglers.

History and legend, fact and fiction are all teased out and explained by your guide who has an extensive background in studying the criminal elements of the city. Of course, it isn't all darkness, and degradation; you'll also enjoy a donut and coffee, on us.

This tour appeals to a wide range of people, from history buffs and true crime heads all the way down to children who are thrilled to see the city in a whole new light.


54 Verified Reviews

The tour was fantastic and gave us a bunch of information about the city.

I have been on those bus tours and they don't give even half of what our provided in the 2.5 hours we were with him. He had some great personal stories also.

We really enjoyed this walk!

Our guide gave so much interesting information. It was probably the best tour we did while in New York. Thank you!


Does this tour run if the weather is bad?
Like all of our tours, this one runs rain or shine. If it's raining we advise that you bring an umbrella. New York can also be very cold in the winter so we advise dressing in layers and wearing a warm set of gloves or mittens.