New York City: Prohibition Walking Tour – With Drinks

If you’re curious about the rebellious spirit of New York City during Prohibition, this walking tour offers a fascinating glimpse into the city’s secretive, often scandalous, nightlife. While I haven’t personally taken this exact tour, the detailed reviews, expert guides, and carefully curated stops make it clear that it’s a well-loved experience for history buffs and nightlife enthusiasts alike.

What we love about this tour is its combination of storytelling, authentic historic venues, and lively atmosphere. You get to visit three of NYC’s oldest and most iconic saloons, each with its own story to tell. The inclusion of Prohibition-style cocktails or beers at each stop means you’re not just listening — you’re tasting a piece of the past. Plus, the guides are noted for their knowledgeable, personable insights, which make the stories come alive. A potential downside? The whole experience is limited to those 21 and older, so it’s not suitable for younger travelers or those with mobility issues. But for anyone interested in history, cocktails, or a lively walk through the city’s underworld, this tour offers a compelling mix.

This tour is best suited for history buffs, nightlife lovers, and those looking for a fun, educational experience that combines walking, storytelling, and drinks. Its compact 2-hour format makes it manageable even for busy days, and the price of $89 per person provides a good value when considering the included drinks, the exclusive access to historic venues, and the expert narrative. Now, let’s explore what makes this tour stand out in detail.

Good To Know

• Historic Venues: Visit three of New York’s oldest and most storied saloons
• Expert Guides: Guides are praised for their knowledge and personable storytelling
• Prohibition Era Stories: Learn about gangsters, bootleggers, and political corruption
• Included Drinks: Enjoy a beer or Prohibition-style cocktail at each stop
• Authentic Atmosphere: Experience NYC’s underworld haunts from the Prohibition era
• Compact and Manageable: The 2-hour walk suits most schedules and energy levels

This is a walking journey through some of Manhattan’s most historic neighborhoods, focusing on the story of Prohibition and its underground culture. Starting at the Great Hall Cooper Union, a prominent meeting place turned tour start point, you’ll be greeted by your friendly, knowledgeable guide — Earl, in the reviews, is especially praised for making the experience engaging and personable.

The tour runs for approximately 2 hours, usually in the afternoon, making it a flexible addition to your day without being overly taxing. Expect to walk at a leisurely pace through the streets, with stops at three historic saloons that have seen the city’s most notorious figures and political machinations.

Throughout the walk, your guide will share stories about gangsters, bootleggers, and powerful political figures linked to Tammany Hall. These stories aren’t just dry history; they paint a vivid picture of how these saloons served as hubs for organized crime and corruption. You’ll likely hear about famous figures who frequented these places, as well as how speakeasies operated in secrecy amidst the city’s bustling streets.

The Saloon Stops: A Closer Look

Each of the three venues visited on this tour has its own character and history. While the specifics of each venue aren’t detailed here, the focus is on their age and significance in NYC’s boozy past. These are not modern bars dressed up for travelers but long-standing establishments with authentic histories. Visiting these venues means stepping into spaces that have hosted notorious criminals, political power players, and everyday New Yorkers seeking a clandestine drink.

Guests report that the saloons are “not just places to drink—they were hubs for organized crime and corruption,” making each site feel like a portal into the city’s gritty past. The stories shared by guides are vivid, with anecdotes about mobsters, bootleggers, and political dealings that give depth to each stop.

Drinks and Atmosphere

For each saloon, you’ll receive a Prohibition-style cocktail or beer included in the tour price. This thoughtful touch offers a taste of what patrons might have sipped during the era — think classic cocktails or era-appropriate brews. The drinks serve as a memorable way to connect with the theme, and reviewers consistently mention that the drinks are better than expected, adding to the authentic vibe.

The atmosphere in these historic venues is a mix of nostalgia and lively storytelling. Many patrons mention feeling like they’re “going to old bars with a friend,” which speaks to the guides’ ability to create a relaxed, fun environment while sharing serious history.

The Tour Guide: Earl and Beyond

Multiple reviews highlight Earl’s expertise and personable style, which elevates the entire experience. He’s credited for making the stories engaging and accessible, with one reviewer mentioning, “Earl was fantastic! Very knowledgeable and personable.” The guides’ ability to weave stories of gangsters and political corruption into the fabric of NYC’s streets helps make the history tangible.

Ending at a Legendary Saloon

The tour concludes at a “legendary saloon,” where guests can toast to the city’s past and reflect on what they’ve learned. This final stop leaves a lasting impression—both as a social experience and as a taste of NYC’s resilient nightlife culture.

At $89, the value hinges on the quality of storytelling, the historic venues, and the included drinks. Considering the three stops, the drinks, and the stories, most reviewers see this as a fair price for an engaging, immersive experience. The small group size, guided by a personable expert, ensures you get plenty of attention and insider details.

While it’s a short tour, its depth and authenticity make it worthwhile for those interested in NYC’s rebellious past. It’s especially appealing if you enjoy learning through stories and visiting historic venues with character.

Practical Tips for Visitors

• Be prepared to walk and stand for the duration; wear comfortable shoes.
• Bring a valid ID, as the tour is only open to those 21 and older.
• Arrive at the meeting point, the Great Hall Cooper Union, 15 minutes early.
• If you’re interested in the stories behind organized crime and political corruption, this tour will satisfy that curiosity.
• Consider this experience as a fun, educational addition to your NYC itinerary, especially if you like history and good drinks.

History buffs and nightlife enthusiasts will get the most out of this experience, as it offers a well-rounded mix of storytelling, historic venues, and drinks. It’s perfect for travelers looking for something different from typical sightseeing — a peek into the city’s wilder, more clandestine past.

This tour is less suited for those with mobility challenges or anyone under 21. It’s also ideal for small groups who appreciate guided storytelling and authentic atmospheres over modern bar scenes.

This Prohibition Walking Tour with Drinks delivers a lively, informative look at New York City’s nostalgic underworld. With a knowledgeable guide, visits to historic saloons, and the chance to sample era-appropriate drinks, it offers a memorable journey into a rebellious chapter of the city’s history. While it’s a short experience, the depth of stories and authenticity of the venues make it worth considering for anyone interested in the city’s colorful past.

If you enjoy learning about old New York, hearing tales of gangsters and corrupt politicians, and sipping cocktails that fit the era, this tour balances fun and education perfectly. It’s a great choice for curious travelers who want an engaging, relaxed, and authentic slice of NYC history.

Is this tour suitable for children? No, the tour is strictly 21+ due to alcohol consumption and age restrictions.
How long does the tour last? The tour is approximately 2 hours, making it easy to fit into most itineraries.
Where does the tour start? It begins at the Great Hall Cooper Union, a notable historic meeting space.
Are the drinks included? Yes, each stop includes a Prohibition-style cocktail or beer, with a total of 3 drinks per person.
Is the tour walkable for most people? Yes, but it involves walking through city streets, so comfortable shoes are recommended.
Can I cancel the tour? Yes, you can cancel up to 24 hours in advance for a full refund.
Is the tour private or small group? It typically runs with a small group, guided by a personable expert, ensuring personalized storytelling.
What makes this tour stand out? Its focus on the historic saloons, authentic tales, and the expert guide’s storytelling ability.
Do I need to book in advance? Yes, booking ahead is recommended, especially since reviews highlight Earl’s engaging guides as a highlight.

This tour offers a compelling mix of history, fun, and spirits, perfect for anyone eager to explore New York’s rebellious, cocktail-soaked past.