Guided tour

New York City: Stories from the Dark Side

New York City: Stories from the Dark Side

From $59 per person

This tour delves into the darker side of New York history. Learn about the shocking truth behind the city’s organized crime rings, white collar swindlers and modern scandals.

About this activity

Free cancellation
Cancel up to 24 hours in advance to receive a full refund
Covid-19 precautions
Special health and safety measures apply. Learn more
Mobile ticketing
Use your phone or print your voucher
Duration 2.5 hours
Check availability to see starting times.
Instant confirmation
Live tour guide
Wheelchair accessible


  • Walk the beat with an expert guide who will show you through the criminal past of NYC
  • Discover the turbulent histories of domestic and immigrant gangs in New York, including the notorious Irish and Italian gangs
  • Enjoy a group with a maximum of 20 people
Full description
Take to the streets of New York with an expert guide to explore neighborhoods once home to notorious criminals, learn how the city was ruled in waves by various immigrant crime rings and finding out what modern crime looks like in the city. On the Lower East Side, you’ll see tenement buildings where Irish immigrants lived in subhuman conditions. The most notorious area here was the ‘Five Points’ - a junction so infamous for its gang crime (rumor has it some even lived in burrows under the streets!) that Charles Dickens came to check it out himself on a trip to NYC, not believing it could live up to its status. It did, of course, as your guide will tell you. Irish gangs weren’t the only group to terrorize the Lower East Side, however. Throughout the 1900s the Italian mafia kept Little Italy in a choke hold, while the 1970s and 1980s were dominated by Chinese turf wars so bloody, you’ll hardly believe it. From the city’s earliest rag-tag gangs to the mafia empires of the 20th century, separate the truth from myths popularized by movies like Gangs of New York and TV shows like the Sopranos. Also learn about the city’s most notorious criminals; from Captain Kidd and Boss Tweed, to John Gotti and Leona Helmsley. The neighborhoods you visit are much nicer today than they were in the past, but has NYC really cleaned up its act? As part of your tour you’ll visit lower Manhattan, in particular Wall Street and the Financial District, to learn about modern, white collar crime (and the going rate for a get-out-of-jail-free card).
  • Guided tour of the Lower East Side and Wall Street
  • Expert tour guide
  • Gratuities
  • Hotel pick-up and drop off
Covid-19 precautions
Traveler requirements
  • You are required to bring and wear a mask

Select participants and date



Prepare for the activity

Meeting point

In front of Stock Exchange on Broad Street between Wall Street and Exchange Place. The exact address is 11 Wall St, New York, NY 10005, USA.

Open in Google Maps ⟶
Important information

What to bring

  • Comfortable shoes

Know before you go

  • This tour may not be suitable for young children, as the subject matter may be graphic and disturbing
  •  This tour is offered in English only
  •  There is a maximum group size of 20 participants
  • The walking portion of this tour is outdoors, rain or shine so please dress appropriately
Customer reviews

Overall rating

3 /5

based on 2 reviews

Review summary

  • Guide
  • Value for money
  • Service
  • Organization

Sort by:

Traveler type:

Star rating:

December 4, 2017


December 8, 2019

Organized by

Product ID: 63726