New York City Mafia Tour with Food Tastings: the Insider’s Story

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  • 3 hr

Walk in the footsteps of New York’s gangsters in the East Village & Little Italy. Hear the inside stories shared with us by a former Mafia associate turned NYPD detective & eat delicious Italian food.

Itinerary Details

Get the insider's perspective on the infamous Mafia crime families of New York City on this walking tour with two sit-down tastings included, through the vibrant and fascinating gangland area of New York’s East Village and Little Italy. On your tour, you will: 

  • Enjoy the attention of your local guide, an NYC Mafia expert who will regale you with personal inside stories of our 'guy in New York', a former Mafia associate turned NYPD Detective and now retired. (You may even meet “our guy” Dennis at one of the restaurant stops on your tour!)
  • Uncover Crime Family member hang-outs,  where they ate, partied and ran their elusive "family businesses". Visit the locations most don’t even know exist. From Prohibition-era bootlegging operations run by the Mafia to the former Gambino headquarters "The Ravenite Social Club", while hearing about Mafia business dealings from money laundering and racketeering to narcotics and assassinations.
  • Tour the East Village where you will learn the complex origins of the Mafia in New York City, and learn the hierarchies within each crime family from the foot soldiers, to the captains and the ‘Boss’.
  • Walk in the footsteps of famed mobsters like Lucky LucianoJoe ‘the boss’ MasseriaJohn Gotti – the Teflon Don“Vinny the Chin” and “Crazy Joe” Gallo, as you hear about their lives, and their crimes.
  • Learn about the Mafia ‘omerta blood oath initiations for recruits, the ‘unwritten rules’ and ‘sit downs’.
  • Visit local, historic food joints --including the room where the Mafia was formed -- for Italian style dinner tastings, including a "primo" and a "secondo piatto". Any drinks you wish to have, you may purchase on the day of the tour. 
  • End your tour with a delicious ‘dolce’, a cream-filled Sicilian Cannoli at the best pastry shop in town.
The stories of the violent and elusive underworld of the Mafia have captivated each of us – with a whole genre of movies and novels dedicated to New York’s gangsters.  On this tour, you immerse yourself in that world, become familiar with the characters, their history, the places, and the unbelievable real-life events thanks to the insider information shared with our small team of expert guides, by a retired Detective and former associate of the Mafia. 

On this tour, you will learn about the Mafia’s origins in the early twentieth century, from their inception of factional wars with one another. That bloody power struggle ended in 1931 when ‘Lucky’ Luciano and fellow Mafia bosses formed the ‘Commission’ of the five New York crime families. ‘Cosa Nostra’ was born, in a discreet back room – where you will eat your first course and begin your journey through New York’s gangland.  

Learn about the most notorious gangsters and their crimes at the very places where they lived, worked, parties were murdered or arrested. Hitmen like Umberto Valenti ‘the Ghost’ (because he was so quick at disappearing after a shoot out), crazy Joe GalloVinny the Chin – who walked around town in his pyjamas and dressing gown muttering to himself, faking madness to avoid arrest for decades  – and John Gotti, known as the ‘Teflon Don’ for his long evasion of the police. Hear about the highest-ranking Mafia turncoat: Sammy “The Bull” GravanoGotti’s under-boss, whose confession finally landed Gotti in jail. 

If you’re into criminal history, the Mafia, or gangsters, then this larger-than-life tour will more than deliver. You’ll hear about the spying, the escapes, the hitmen, drug running, double-crossing, criminality and all the drama of this most sinister yet riveting world of gangsters, while also indulging in delicious Italian food at some of Little Italy’s best joints. 

Tour duration
3 hours

Type of tour
Walking tour - the cost of all public transport is not included between sights. Your guide will help you with this.

Tickets included
  • Two sit down tastings and a Sicilian cannoli 

Other inclusions
  • Gratuities optional
  • Drinks are not included but can be purchased 

Suitable for
Adventurous, Culture Vulture, Foodies, Looking for Local

Attractions along this route:

Little Italy NYC
Little Italy is a neighbourhood in Lower Manhattan in New York City, centred around Mulberry Street, known for its Italian population, shops and restaurants.

East Village NYC
The East Village is a neighbourhood on the East Side of Lower Manhattan in New York City. It is known for its multicultural population, vibrant food, drink and art scene.

John Gotti
John Gotti was an American gangster and boss of the Gambino crime family in New York City. Known as ‘the Teflon Don’, he was caught by the NYPD at the Ravenite Club in 1992.

New York Mobsters
Get Acquainted with local mobsters like Lucky Luciano, Joe Masseria and Meyer Lansky.

Mulberry Street
Mulberry Street has historically been associated with Italian-American culture & history since the early 20th century has been the heart of Manhattan's Little Italy.

Hearty Italian food
Delicious Italian meatballs on tour!

Handmade Sicilian Cannoli
Cannoli are Italian pastries consisting of tube-shaped shells of fried pastry dough, filled with a sweet, creamy filling usually containing ricotta—a staple of Sicilian cuisine.

Local Mafia haunts
Open for over 110 years at this location, De Robertis was famous for its cannolis, pignoli, cookies, lemon ice and Mob connections.

Tenement houses
Tenements were low-rise buildings with multiple apartments, often overcrowded and inhabited by immigrants upon their arrival to NYC.

Murder Scenes
Visit the multiple murder locations, including Umberto's Clamhouse where Crazy Joe Gallo was shot.

"Our Guy" in NYC
Dennis is a retired NYPD Detective born and raised in Little Italy where he would do runs for the local gangs from a very young age. Dennis designed this tour, full of insider information, and trained a select team of guides to lead it.
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