The Detectives Who Chased the Mafia Now Lead Walks Through Little Italy
Retired NYPD officers take you from the East Village to Little Italy, through blocks they policed or grew up on, from Carlo Gambino to John Gotti. Cannoli is included.
The walk starts at 302 East 12th Street, on the sidewalk in front of a restaurant that opened in March 1908 and never got around to modernizing. Italian marble carried in the year before. Painted scenes of the old country still on the walls. Through Prohibition the second floor ran a speakeasy selling moonshine made by the founder's wife.
Your guide is a retired NYPD detective. Some of them grew up in Little Italy, and some of them worked the neighborhood in uniform. Three hours later the walk ends at Mulberry and Canal.
Two departure times, and they are not the same walk. The 11:00 AM group starts inside John's with a plate of spaghetti; the 10:00 AM group starts on the sidewalk and skips the restaurant. Both run three hours, both finish with a cannoli in Little Italy.
The tour goes out in all weather. Guiding is in English, and one booking can cover up to 30 people.
True Crime NYC: Mafia Walk with Retired NYPD DetectiveViator · 3 hours · 10:00 AM or 11:00 AM · instant confirmationwww.viator.comThe First Stop Is a Plate of Spaghetti
The 11:00 AM group sits down inside John's before anyone says a word about the Mafia. The room is narrow, the tablecloths are white, and the walls carry scenes of Italy painted in 1907. In the corner sits a candle that has been collecting wax since Prohibition ended and now weighs 250 pounds.
Then the history starts. The guides lay out how a crime family was organized, from foot soldiers up through the captains to the boss. In August 1922 Umberto Valenti came to John's for a peace meeting, was chased to the corner outside and shot dead. By most accounts the gunman was Lucky Luciano, then working for Joe Masseria. No one was ever charged.
Drinks are extra. Gratuities are not included.
Walking South Into Little Italy
From East 12th Street the route works down Second Avenue, where the guides cover the Prohibition years and point out places most walking tours pass. There is a short stop at a community garden along the way. The stops are brief and the pace is walking pace.
In Little Italy the walk reaches 247 Mulberry Street, the Ravenite Social Club, which Carlo Gambino held from the late 1950s and John Gotti ran as his headquarters until it closed in 1993. One of the guides describes living in the neighborhood across both eras. The storefront is a menswear shop now. This stop is a look from the sidewalk.
The walk finishes at La Bella Ferrara on Mulberry Street, a family pastry shop now in its fourth generation, with a full-size cannoli.
Who Is Actually Leading This
The operator is Police Tours, and the premise is the guides. They are retired NYPD, either raised in Little Italy or assigned to the area during their service. The stops are picked for what the guides can say about them firsthand.
The walk dates to 2017, when a retired detective named Dennis O'Leary started it. A Washington Post reporter who took the tour in 2025 wrote that he opens by showing his official NYPD badge.
The listing names two more: a retired detective who served on the department's Special Operations SCUBA team, and a detective the operator says still takes an active role in organized crime investigations. The listing carries a 4.9 average over 1,177 reviews.
Several different guides run the walk, and travelers come back naming the one they got. A guest review posted in September 2026 on the operator's own listing reads: “Ask for Jay, female that is 25 yrs retired from the NYPD. She takes the tour to the next level.”
Before You Book
- Three hours on pavement, rain or shine. Travelers should have at least a moderate level of physical fitness, and the operator does not recommend it for anyone with a walking or leg condition.
- Surfaces along the route are wheelchair accessible, and service animals are welcome.
- The booking covers ages 9 and up. Infants and toddlers are not carried.
- Confirmation is instant and the ticket is mobile. Show it to the guide at the meeting point.
- Cancel at least 24 hours before your start time for a full refund.
- Anyone under 18 will not be served alcohol.
📍 The meeting point is the sidewalk in front of John's of 12th Street, at 302 East 12th Street near Second Avenue, and the guide collects tickets there. Subway and bus lines run close by. Arrive a few minutes early.
The walk lets out at Mulberry and Canal, which leaves you at the south end of Little Italy in the early afternoon with Chinatown starting across the street.