New York City: Prohibition Walking Tour – With Drinks

Introduction

Our review of the New York City: Prohibition Walking Tour – With Drinks introduces an engaging way to explore Manhattan’s clandestine past. Designed for anyone curious about the city’s roaring twenties, gangster legends, and hidden speakeasies, this tour promises a lively mix of history, architecture, and spirits.

What we love about this experience is the expert storytelling that makes history come alive — the guides are clearly passionate and knowledgeable, turning stories of bootleggers and corrupt political machinations into vivid narratives. Plus, the inclusion of three historic saloons ensures you get a taste—literally—of the Prohibition era’s vibrant, if illicit, nightlife.

A potential drawback? Since the tour is focused on historic bars and their stories, it might feel a bit like a pub crawl for those more interested in architecture or broader history. But if you’re after an authentic, spirited glimpse into NYC’s criminal past, this tour hits the mark. It’s perfect for history buffs, nightlife enthusiasts, or travelers craving a fun, insider view of the city’s underground lore.

This tour is especially well-suited for those who enjoy stories of real-life figures, and like their history served with a side of local flavor. Just note, it’s for ages 21 and up, and walking shoes are recommended as you’ll be exploring on foot through some of NYC’s most historic neighborhoods.

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Key Points

• Authentic historical experience: Visit three of NYC’s oldest and most iconic saloons, each with stories of gangsters and bootleggers.
• Expert guides: Knowledgeable storytellers bring to life tales of Prohibition, speakeasies, and political corruption.
• Included drinks: Enjoy a Prohibition-style cocktail or beer at each stop—three drinks in total—giving you a true taste of the era.
• Walking through history: The two-hour tour offers a manageable pace, perfect for those who want a deep dive without a full-day commitment.
• Rich storytelling: Learn about the city’s connection to Tammany Hall and notorious figures, making history engaging and memorable.
• Legendary finale: The tour concludes at a renowned saloon, with the opportunity to toast to NYC’s gritty past.

Exploring the Tour in Depth

Starting Point and Overall Structure

The tour begins at the Great Hall at Cooper Union, a symbol of New York’s political and social activism. From there, you’ll set out on foot, exploring some of Manhattan’s historic neighborhoods. The walking pace is comfortable, allowing pauses at each saloon for drinks and stories.

The entire experience lasts about 2 hours, which makes it a fantastic afternoon activity, especially if you’re looking to combine it with other sightseeing later. The group size is typically small, fostering a more intimate experience where questions and stories flow naturally.

Visiting the Historic Saloons

Each of the three saloons has its own character and history. These are among the oldest and most iconic watering holes in New York City, some dating back to the early 20th century. Their walls have witnessed the rise and fall of gangsters, the clandestine operation of speakeasies, and the backroom dealings of political machines like Tammany Hall.

What makes these stops special? Besides their age and architecture, they are real places still in operation—meaning you’re stepping into a living piece of history. You’ll feel the weight of the stories as you stand where bootleggers once negotiated deals or mobsters plotted their next move.

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Drinks and Atmosphere

The tour includes one drink per stop—either a beer or a Prohibition-style cocktail. While the drinks are included, they aren’t the main focus; rather, they complement the storytelling, letting you taste the era that the stories evoke.

Guides often share tales of the drinks themselves—how cocktails like the Bee’s Knees or Gimlet became popular during Prohibition, often masked with secret ingredients and elaborate recipes.

Stories and Themes

What really elevates this tour are the stories of notorious figures and the links to Tammany Hall, the powerful political machine that played a significant role during the Prohibition era. Your guide will paint a picture of a city where crime and politics were often intertwined, and where saloons served as hubs for illegal activity and political scheming.

We loved the way guides connect these stories with the physical spaces, making history tangible. One reviewer mentioned Earl, the guide, as “fantastic,” noting his extensive knowledge and personable style—”felt like going to old bars with a friend.”

The Final Saloon

The tour wraps up at what’s considered New York’s most legendary saloon. Here, you’ll get one last toast—symbolically raising a glass to the city’s rebellious spirit and resilience. It’s a fitting end that leaves you with a sense of connection to the city’s underground past.

Price and Value

At $89 per person, the tour is a fair value considering the included drinks, access to historic venues, and the storytelling quality. The experience offers a blend of history, local flavor, and social atmosphere that you might not easily find elsewhere.

Compared to other guided outings, this tour’s focus on authentic, historic bars with drinks included makes it an engaging and immersive option for those interested in the prohibition era and NYC’s criminal past.

Practical Tips

• Wear comfortable shoes: you’ll be walking through neighborhoods, some of which might have cobblestone or uneven surfaces.
• Bring ID: the tour is for those 21 and over.
• Arrive early: being 15 minutes ahead at the meeting point ensures a smooth start.
• Consider your appetite for history and spirits: if you’re shy about alcohol, note that drinks are included, but the focus remains on storytelling.
• Group size: small groups mean more personalized stories and interaction.

Who Would Love This Tour?

This experience is perfect for history buffs who enjoy stories of crime and political intrigue, as well as those seeking a lively, social activity. It’s suited for travelers who appreciate authentic venues and are eager to taste a bit of the city’s hidden past. However, it’s not for those with mobility issues or anyone under 21.

The Sum Up

The Prohibition Walking Tour with Drinks offers a lively, authentic peek into New York City’s colorful past. With knowledgeable guides, historic saloons, and the added fun of included drinks, it’s a smart choice for anyone interested in the city’s underbelly and legendary figures. You’ll go home with more than just photos—you’ll have stories, tastes, and a deeper sense of NYC’s gritty, rebellious spirit.

If you’re up for walking through history, raising a glass to the past, and hearing stories you won’t find in textbooks, this tour delivers. It’s a well-balanced experience that combines education, entertainment, and a taste of the city’s clandestine side.

FAQ

Is this tour suitable for people with mobility impairments?
No, the tour involves walking through neighborhoods, so it might not be accessible for everyone with mobility issues.

Do I need to bring my ID?
Yes, as the tour is for those 21 and over, you’ll need to show a valid ID to participate in the drinks.

What is the meeting point?
The tour begins at the Great Hall at Cooper Union, a notable and central location in Manhattan.

Can I cancel this tour?
Yes, you can cancel up to 24 hours in advance for a full refund, offering flexibility for your travel plans.

How long is the tour?
The experience lasts about 2 hours, making it a great option for a mid-afternoon activity.

Are the drinks included?
Yes, you get one Prohibition-style cocktail or beer at each of the three saloons visited.

Is it a small group?
While not explicitly stated, small group sizes are typical, fostering a more personal and engaging experience.

This tour offers an intriguing mix of history, storytelling, and local flavor, ideal for those who want to see a different side of NYC while enjoying some well-crafted drinks.

You can check availability for your dates here: More Great Tours Nearby