NYC Prohibition Era Speakeasy Tour with Guide

5.0 (one review) 3 hours Free cancellation

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5.0

NYC Prohibition Era Speakeasy Tour with Guide — Photos: the activity supplier, via Viator

NYC Prohibition Era Speakeasy Tour with Guide, photo 2 — Photos: the activity supplier, via Viator

About this activity

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.

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At a glance

Duration: 3 hours
Confirmation: Instant confirmation
Ticket: Mobile or paper ticket accepted
Group: Up to 20 people
People per booking: 1–15
Guide: English
Operated by: CARERI ENTERTAINMENT

Ages: Adults (21–99 years)

What is included

Included

Included: Local guide

Not included

Not included: Alcoholic beverages: Drinks are not included and are optional at the guest’s own expense.
Not included: Gratuities for the guide are optional but reccomended
Not included: Public transportation (bus, subway, cable car, etc.): 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

Grand Central Terminal

45 min

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.
Lower East Side

40 min

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.
Lower East Side

40 min

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.

Meeting point and pickup

Everyone meets at the meeting point.

Meeting point

The guide will be waiting for you inside Grand Central Terminal, near the main clock.

End point

Cancellation

Free cancellation

For a full refund, cancel at least 24 hours before the scheduled departure time.

If you cancel	You get back
At least one day before	100%
Less than a day before	0%

The operator may cancel if too few people book; you then get another date or your money back.

Good to know

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.