New York City’s past is filled with intriguing tales of criminal activity, from notorious street gangs to infamous river pirates. The "Gangs and River Pirates of New York Walking Tour" offers a chance to uncover this captivating history, guiding visitors through the streets of Lower Manhattan. Led by knowledgeable guides, the tour delves into the dark underbelly of the city, revealing stories of extortion, robbery, and the powerful figures who once prowled the bustling docks. With a perfect 5.0 rating, this engaging experience promises to transport participants back in time, leaving them eager to discover more about New York’s shadowy past.
Key Points
- The 3.5-hour walking tour explores the criminal underworld of Lower Manhattan, including notorious gangs like the Dead Rabbits and Five Points Gang.
- Participants will learn about river pirates such as Willy "the Actor" Sutton and Captain Kidd who operated along the city’s waterways.
- The tour is led by a licensed guide and provides a hassle-free experience, with gratuities and cancellation policy included.
- The tour is wheelchair and stroller accessible, but not recommended for those with back problems or serious medical conditions.
- With a 5.0 overall rating and praised for its engaging storytelling, the tour offers a captivating glimpse into New York’s dark criminal past.
Tour Overview

The Gangs and River Pirates of New York Walking Tour takes participants on a journey through the storied past of Lower Manhattan.
Priced from $38.00 per person, this 3.5-hour tour explores the city’s criminal underworld, led by a licensed guide.
With a maximum group size of 30 travelers, the tour departs at 3:30 PM from the South West corner of Columbus Park.
Wheelchair and stroller accessible, the tour ends at Coenties Slip and Stone Street.
Suitable for those with moderate fitness, the tour isn’t recommended for travelers with certain medical conditions.
Guests can reserve now and pay later, with free cancellation up to 24 hours prior.
You can also read our reviews of more walking tours in New York City
Inclusions

The Gangs and River Pirates of New York Walking Tour includes a licensed tour guide to lead participants through the tour.
Gratuities are also covered as part of the tour price. Customers have the flexibility to cancel their booking up to 24 hours before the tour starts without any penalties.
The tour also offers a Reserve Now and Pay Later option, making it convenient for travelers to secure their spot.
These inclusions provide a hassle-free experience, allowing participants to focus on exploring the rich history and stories of the city’s notorious gangs and river pirates.
Accessibility and Restrictions
The Gangs and River Pirates of New York Walking Tour is wheelchair accessible and stroller accessible, making it inclusive for travelers with mobility needs.
Service animals are also allowed on the tour. However, it’s not recommended for those with back problems, pregnant travelers, or those with serious medical conditions as the tour requires a moderate level of physical fitness.
The tour route is near public transportation, providing convenient access for visitors.
Reviews
Reviewers have offered overwhelmingly positive feedback for the Gangs and River Pirates of New York Walking Tour.
The tour boasts a 5.0 overall rating based on a single review. Reviewer Joe_F, who experienced the tour in September 2024, praised guide Ramona as "fantastic" and "super knowledgeable," commending her ability to bring the past to life in an engaging and informative way.
The reviewer highly recommends the tour, highlighting Ramona’s expertise and the tour’s captivating nature.
With a perfect rating and glowing testimonial, the Gangs and River Pirates of New York Walking Tour appears to be a must-do experience for visitors to Lower Manhattan.
The History of Lower Manhattan
As the tour explores the historical landscape of Lower Manhattan, participants explore the vibrant and gritty past that has shaped this iconic New York City district.
From the days of Dutch colonial rule to the rise of industry and immigration, Lower Manhattan has witnessed the growth and evolution of the city.
The tour highlights key moments in the area’s history, including:
- The construction of the original Wall Street fortification in the 17th century.
- The development of the port and the influx of merchants, traders, and river pirates.
- The emergence of organized crime and the formation of notorious gangs like the Five Points Gang.
- The transformation of the neighborhood into a bustling financial center and commercial hub.
- NYC: Snow Tubing and Brewery Visit Day Trip
★ 4.7 · 51,195 reviews - NYC: Empire State Building Tickets – Observatory & Museum
★ 4.7 · 25,757 reviews - New York City: Top of the Rock Observation Deck Ticket
★ 4.6 · 19,097 reviews - New York City: Statue of Liberty & Ellis Island With Ferry
★ 4.6 · 18,683 reviews - New York City: American Museum of Natural History Ticket
★ 4.5 · 15,447 reviews - NYC: Museum of Modern Art (MoMA) Entry Ticket
★ 4.6 · 12,540 reviews
Notorious Gangs and River Pirates
Although New York City’s Lower Manhattan had long been home to a thriving port and commercial activities, it also gave rise to notorious gangs and river pirates who operated along the waterways. These criminal elements took advantage of the bustling docks and vulnerable ships to extort, rob, and terrorize. Notable gangs included the Dead Rabbits and the Bowery Boys, while infamous river pirates like Willy "the Actor" Sutton and Captain Kidd plundered ships for their riches. This dark underbelly of New York’s past is explored in the Gangs and River Pirates of New York Walking Tour.
| Notorious Gangs | Infamous River Pirates |
|---|---|
| Dead Rabbits | Willy "the Actor" Sutton |
| Bowery Boys | Captain Kidd |
| Five Points Gang | Barnacle Bill |
Notable Landmarks
The walking tour takes guests through several notable landmarks that showcase New York City’s gritty past.
Along the way, visitors will see:
-
The South Street Seaport, where notorious river pirates once operated their illicit activities along the docks.
-
Coenties Slip, a former hub of criminal activity that’s now a charming cobblestone street.
-
45 Stone Street, a historic building that was once a notorious gambling den.
-
Columbus Park, a public space that was once the center of several notorious gangs’ turf wars.
These landmarks provide a window into the city’s tumultuous history and the ruthless individuals who shaped it.
Additional Tours
Additional tours offered by Tommy’s New York include an "Organized Crime Walking Tour" that explores the history of the notorious Mafia families in Lower Manhattan.
There is also a "Prohibition-Era Speakeasies" tour that takes guests through the hidden underground bars and social clubs that flourished during the 1920s.
These specialized tours provide unique insights into the city’s storied past, catering to a range of interests beyond the Gangs and River Pirates experience.
Visitors seeking a deeper dive into New York’s criminal underworld or the era of bootlegging can choose from Tommy’s diverse lineup of historical walking tours.
Frequently Asked Questions
How Much Time Is Allocated for the Tour?
The tour lasts approximately 1.5 hours, starting at 3:30 PM and ending at the Coenties Slip and Stone Street location. It’s a walking tour that covers the history of Lower Manhattan.
What Language(S) Are the Tours Conducted In?
The tours are conducted in English. The tour operator does not specify offering tours in any other languages based on the provided information.
Is Photography Allowed During the Tour?
Photography is generally allowed during the tour, though guests are advised to check with the tour guide at the start of the experience. Most tours welcome photos, but there may be some restrictions in certain areas.
Are There Any Age Restrictions for Participants?
The tour doesn’t have any age restrictions, and it’s open to travelers of all ages. However, it’s not recommended for children under 12 or those with limited mobility, as it requires a moderate level of physical fitness.
What Are the Payment Options for the Tour?
The tour offers a Reserve Now and Pay Later option, allowing travelers to book the experience now and pay later. Plus, the tour is priced at $38.00 or more per person.
Gangs and River Pirates of New York Walking Tour
Sum Up
The "Gangs and River Pirates of New York Walking Tour" offers a captivating exploration of Lower Manhattan’s criminal past. Led by a knowledgeable guide, the tour delves into the notorious gangs and infamous river pirates that once thrived along the bustling docks. With a perfect 5.0 rating, it’s a must-do for history enthusiasts seeking an immersive glimpse into the city’s dark underbelly.





























