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NYC Prohibition Era Speakeasy Tour with Guide

5.01 reviewGrand Central Station

  • 3 hours
  • Free cancellation up to 24h before
  • Guided in English
  • Instant confirmation

Highlights

Meet your guide under the iconic clock at Grand Central Terminal and step back into the 1920s for an evening exploring New York City’s hidden Prohibition-era nightlife. Follow in the footsteps of bootleggers, mob bosses, and socialites as you uncover the city’s underground bar scene. During the tour, you’ll visit three historic speakeasies, each with its own story of secret parties, elite gatherings, and underground drinking. At one stop, enjoy free time to relax and have a traditional drink. Drinks are optional and at the guest’s own expense. Your guide will share tales of Prohibition-era New York, including organized crime, bootlegging routes, and how New Yorkers enjoyed nightlife despite the ban. The tour combines history, true crime, and social storytelling for a fun, immersive night out. The tour concludes at a former gangster hangout, revealing how mob networks shaped the city’s nightlife.

Inclusions

What's included

  • Local guide

What's not

  • Drinks are not included and are optional at the guest’s own expense.
  • Gratuities for the guide are optional but reccomended
  • The subway fare is not included and is at the guest’s expense. It can be paid directly using a contactless credit/debit card or a smartphone.

Itinerary

  1. Meet your guide inside Grand Central near the main clock. Your first stop is a historic speakeasy hidden inside the terminal. Discover how elite New Yorkers secretly drank during Prohibition and hear fascinating stories about underground parties and high-society nightlife in the 1920s.

    45 min

  2. Travel by subway to the Lower East Side and visit one of the city’s oldest tavern-style bars. Learn how immigrant communities and saloon culture shaped New York’s social scene.

    40 min

  3. End the tour at a historic nightlife spot linked to organized crime. Hear stories about bootlegging operations, mob bosses, and how underground networks kept the city’s nightlife alive.

    40 min

Cancellation

Free cancellation up to 24 hours before the experience starts, for a full refund.

Reviews

5.0

  • 51
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Ratings come from 1 reviews collected by our booking partner. They are travellers' own words, in the order they were written — never reordered to flatter the experience.

Know before you go

Meeting point
The guide will be waiting for you inside Grand Central Terminal, near the main clock.
Pickup
Everyone meets at the starting point; there is no pickup.
Ticket type
Mobile or paper ticket accepted
Group size
Up to 20 travellers
Operated by
CARERI ENTERTAINMENT
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Guests under 21 years old are not allowed to participate. Please bring a valid form of identification.

How it compares in New York City

  • Its from-price is 58% below the median of the 692 city tours we list in New York City.
  • Its length is typical for the group.
  • By number of reviews it ranks 458 of 692.
  • The operator lists free cancellation on it.

About New York City

New York City packs skyscrapers, famous museums, Broadway theatres and dozens of distinct neighbourhoods into five boroughs that hum day and night.

Manhattan is the classic first stop. Times Square glows above the theatre district, Central Park stretches for blocks between the Upper East and Upper West Sides, and the Empire State Building, the Chrysler Building and Rockefeller Center define the midtown skyline. Downtown, the 9/11 Memorial, Wall Street and the Brooklyn Bridge sit close together, and boats run out past the Statue of Liberty to Ellis Island.

Top-ranked sights in New York City: Statue of Liberty, Central Park, National September 11 Memorial & Museum.

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