New York City: Prohibition Walking Tour

If you’ve ever wondered what it was like to sip a cocktail during the days when alcohol was outlawed, this Prohibition Walking Tour in New York City offers a front-row seat. Starting at the iconic Great Hall of Cooper Union, this two-hour stroll takes you through some of the city’s oldest and most storied saloons, where history, drinks, and lively stories collide. For $89 per person, you get three drinks—one at each stop—and a chance to walk in the footsteps of gangsters, bootleggers, and political operatives from the Prohibition era.

Two standout features make this tour particularly compelling. First, the guides are genuinely knowledgeable and personable—a sentiment echoed in reviews praising Earl’s storytelling and enthusiasm. Second, the experience offers a rare glimpse into New York’s underworld, with tales about Tammany Hall, organized crime, and speakeasies that truly bring history to life. It’s both entertaining and educational, with a focus on authenticity.

A possible consideration is the strict age restriction of 21+, which means this isn’t suitable for younger travelers or those with mobility issues. Also, since it’s a walking tour, comfortable shoes are a must. The tour’s value shines if you’re interested in history, enjoy a good story, and want to experience some of the city’s authentic, historic drinking spots. It’s perfect for curious adults who love a blend of culture and cocktails.

Key Points

Historic Saloons: Visit three of New York’s oldest and most renowned drinking establishments.
Inclusions: Enjoy a drink at each stop, from beers to Prohibition-style cocktails.
Stories & History: Learn about gangsters, bootleggers, and political corruption tied to the city’s past.
Expert Guides: Guides like Earl bring the stories to life with engaging anecdotes.
Authentic Experience: The tour offers a real feel for the city’s underbelly during the Prohibition era.
End at a Legendary Saloon: The tour concludes with a toast in one of NYC’s most iconic bars.

You can check availability for your dates here:

Starting Point at the Great Hall of Cooper Union

The tour begins at the Great Hall in Cooper Union, a historic and architecturally impressive venue that sets a serious tone for what’s to come. Meeting here offers a central and accessible location, with directions easily available online. The meeting time is usually in the afternoon, and arriving 15 minutes early helps you settle in and meet your guide, Earl, whose reputation for deep knowledge and personable style is a highlight from reviews.

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What to Expect During the Walk

Once the group gathers, you’ll set out on a walk through some of Manhattan’s most historic neighborhoods. Your guide will weave stories of organized crime, political corruption, and prohibition-era speakeasies. The walking pace keeps it relaxed enough for questions and observations, and the stops are carefully chosen to showcase the essence of the period.

Each of the three saloons has a story. These aren’t just bars—they’re living museums, with histories that stretch back over a century. As you enter each, expect to be greeted with a drink, often a Prohibition-style cocktail or a beer, included in the ticket price. The drinks are served in settings that are as close to the original speakeasies as possible, often with vintage decor and a cozy, clandestine feel.

Visiting Three Historic Saloons

First Stop: The Oldest Saloon in Town

The journey begins at one of the city’s oldest watering holes, known for its ties to notorious figures of the era. Expect stories about gangsters and bootleggers who used this spot as a base for their operations. The guide’s narration makes the history vivid, drawing connections between the past and present.

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Second Stop: A Hidden Speakeasy

Next, you’ll enter a place that was once a secret speakeasy during Prohibition. Here, the focus is on how these secret bars operated and the role they played during a lawless period. The guide will share stories of famous figures who frequented these establishments, giving you a taste of the illicit nightlife that thrived beneath the city’s surface.

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Final Stop: Legendary Saloon and Toast to History

The tour ends at a famous NYC saloon, known for its colorful past and legendary clientele. This is the perfect spot to reflect on what you’ve learned, share impressions with fellow travelers, and raise a final toast to the city’s gritty past. From reviews, we know that participants love Earl’s storytelling, describing him as personable, knowledgeable, and able to make history approachable.

The Drinks and Their Significance

Each stop’s included drink adds flavor and authenticity. You might find yourself sipping a Prohibition-era cocktail like a Bee’s Knees or a classic beer, which helps bring the era to life. Having drinks served at each location makes the experience more immersive and social, turning a simple walk into a lively, shared adventure.

The Guide and the Experience

Guides like Earl are central to the tour’s success. As noted in reviews, the guides are well-versed and personable, making the history feel like stories shared among friends. This creates a relaxed and engaging atmosphere where you feel comfortable asking questions and soaking in the stories.

Practicalities and Considerations

The tour lasts about 2 hours, which is just enough time to get a sense of the history without feeling hurried. Group sizes tend to be manageable, and the tour is offered in English. Since it involves walking and some standing, comfortable shoes are a must. The age restriction of 21+ means you’ll be with adults sharing a common interest in NYC’s lively past.

The tour’s price of $89 includes three drinks and all the stories. Compared to the cost of visiting these historic bars individually, this offers good value, especially considering the guide’s expertise and the immersive atmosphere. It’s a memorable way to combine history, culture, and a taste of New York’s underground past.

Authenticity and Educational Value

What sets this tour apart is its focus on real stories and authentic locations. The tales of Tammany Hall, organized crime, and speakeasies are woven into the stops, giving you a deeper understanding of how politics and crime often went hand-in-hand in shaping the city. The stories aren’t sanitized—they’re gritty, revealing the city’s complex past.

What Reviewers Say

Praise centers on the guides’ storytelling skills. Kerrie called Earl “fantastic,” noting his knowledge and personable style, while TJ appreciated feeling like they were “going to old bars with a friend.” The positive feedback emphasizes that the guide’s ability to make history relatable greatly enhances the experience.

Who Should Sign Up?

This tour is ideal for adults interested in history, culture, and NYC’s legendary nightlife. If you’re curious about the city’s underworld or love a good story with your drinks, you’ll find this tour engaging. It’s especially suitable if you prefer small, intimate groups and enjoy learning in a relaxed setting.

The New York City Prohibition Walking Tour offers a well-balanced blend of history, storytelling, and authentic drinking spots that transport you to a different era. For $89, you gain not only three drinks but also a vivid picture of a city that thrived in its lawless days, with guides like Earl making the past accessible and fun. The experience is perfect for travelers who love a bit of intrigue and want to see the city’s historic neighborhoods through the lens of its clandestine nightlife.

If you’re eager to uncover hidden stories behind NYC’s oldest bars and enjoy a lively, educational walk, this tour delivers a memorable slice of city history—one drink and story at a time.

Is this tour suitable for non-drinkers?
No, the tour is 21+ and includes three drinks as part of the experience. If you don’t drink alcohol, this might not be the best fit.

How long does the tour last?
The walking tour lasts approximately 2 hours, making it a manageable and enjoyable way to explore without overdoing it.

Are the saloons accessible for people with mobility issues?
The experience isn’t suitable for people with mobility impairments, as it involves walking and possibly uneven surfaces.

Where does the tour start?
It begins at the Great Hall in Cooper Union, a central, easily accessible location in Manhattan.

Is it possible to cancel or reschedule?
Yes, you can cancel up to 24 hours in advance for a full refund, and you can reserve now and pay later to keep your plans flexible.

What should I bring?
Comfortable shoes, an ID card, and an eagerness to hear some lively stories about NYC’s past.

This walking tour offers an engaging way to step back into New York’s Prohibition days, combining authentic history with a social atmosphere—you might just find yourself seeing the city in a whole new light.