New York City Prohibition Walking Tour

A Glimpse into the Gritty Past of New York City: The Prohibition Walking Tour

When you think of New York City, images of soaring skyscrapers and bustling streets probably come to mind. But beneath the modern skyline lies a fascinating history of lawlessness, secret bars, and political corruption, especially during the Prohibition era. For those curious about the city’s less-polished past, the New York City Prohibition Walking Tour offers a compelling two-hour journey through some of its oldest, most storied saloons. Led by knowledgeable guides, this tour is priced at $47.20 per person, a modest fee considering the treasure trove of stories and authentic locations you’ll encounter.

What we love about this tour is how it combines history, architecture, and local lore into a manageable walk. First, you’ll visit McSorley’s Old Ale House, an institution that has survived prohibition and countless other upheavals. It’s not just a drink stop; it’s a step back in time, with stories shared by guides that breathe life into the walls. Second, the walk through Little Italy offers a glimpse of immigrant life and how speakeasies secretly operated within that vibrant neighborhood. The third highlight is the Old Town Bar, famous for its original interiors — a true relic that has seen everything from Prohibition to modern New York.

One potential consideration is the moderate physical activity involved in walking through historic neighborhoods, which might be a stretch for some. The tour’s length and pace are designed to be engaging but not exhausting, making it suitable for most ages and fitness levels. If you enjoy stories of organized crime, political shenanigans, and urban architecture, this tour is particularly well-suited for history buffs, architecture lovers, or anyone wanting a different perspective on NYC beyond the usual skyscraper tour.

Key Points

• Authentic Historic Saloons: Visit four legendary bars, including McSorley’s and Pete’s Tavern.
• Engaging Storytelling: Guides share inside stories about gangsters, bootleggers, and political corruption.
• Neighborhood Insights: Walk through Little Italy and Gramercy Park, learning about their Prohibition-era transformations.
• Cost-Effective: At under $50, it offers a well-rounded experience of NYC’s secretive past.
• Flexible Experience: You can choose to buy drinks at some stops; the tour itself covers the stories, not the beverages.
• Convenient Locations: Easy meeting points near public transportation make it accessible for most visitors.

A Closer Look at the Prohibition Walking Tour

If you’re eager to piece together a different story of New York City, this tour offers a well-structured introduction to the city’s hidden history. It’s designed to be both educational and entertaining, with stops that are intrinsically linked to the city’s vibrant past of illegal alcohol trade, political machinations, and social change.

The tour begins at McSorley’s Old Ale House, one of NYC’s oldest bars, founded in 1854. It’s a perfect starting point because this pub survived the Prohibition era by cleverly operating as a tobacco shop, then re-emerging as a drinking spot. Your guide, “Billy” (if reviews are anything to go by), will share tales of gangsters such as the infamous Dutch Schultz and how the bar became part of the underground scene.

From there, your walk takes you through Little Italy, where your guide will describe how immigrant communities secretly hosted speakeasies amid their lively streets. Expect stories about how these hidden bars operated under the radar, often in basements or back rooms, serving as social hubs for Italians and other immigrants. Walking through this neighborhood provides an authentic feel of the tight-knit, sometimes clandestine, community life of the early 20th century.

Next, you’ll step into Old Town Bar, a genuine time capsule with its original interiors — a rare find in a city where so many historic spots have been renovated or replaced. Here, you’ll hear about notable figures who drank in these establishments during Prohibition and how these bars maintained a semblance of normalcy amid the chaos. The stories shared by staff and guides make these places come alive, revealing the resilience of local businesses.

The tour continues to Gramercy Park, a neighborhood with a rich history of political movements. Your guide will explain its importance during Prohibition, highlighting its connections to political figures and how the area played a role in resisting or navigating the restrictions on alcohol. The park itself, a private oasis, symbolizes the old-world exclusivity of certain parts of the city, adding a touch of elegance to the gritty stories.

Finally, you’ll conclude at Pete’s Tavern, another historic NYC bar that has been in continuous operation since 1864. Known for its literary patrons and secretive past, Pete’s Tavern offers a fitting finale. You might enjoy a drink here, with the stories of Prohibition secrets lingering in the air, and a sense of continuity that these spots still thrive today.

Why This Tour Adds Value

For the inquisitive traveler, the appeal of this walking tour lies in its balance of authentic locations and storytelling. Unlike a typical sightseeing tour that might just point out buildings, this experience brings the past vividly to life. You’ll learn that these saloons weren’t just bars but symbols of resistance, community, and sometimes, corruption.

The price point of just over $47 is quite reasonable considering the level of detail and the number of venues visited. Each stop offers a chance to soak in the atmosphere of a bygone era, often in beautifully preserved interiors. Plus, with the option to purchase drinks, you can choose to relax and linger in these historic settings, making the experience personal and memorable.

The tour’s group size, limited to 40 travelers, ensures that guides can keep the stories engaging and personalized. The walking pace is moderate, typically around 30 minutes per stop, making it accessible without feeling rushed. It’s an ideal choice for those who prefer walking tours over bus trips, as the city streets themselves are part of the story.

One of the standout aspects is the inside knowledge shared by guides, sometimes including stories from staff members who have worked at these establishments for years. These details add authenticity and a sense of being ‘in the know’ about NYC’s secret past. Visitors have noted that the stories of gangsters and bootleggers are “especially entertaining,” giving a lively flavor to the historical facts.

Practical Details and Tips

Meeting point: The tour starts at Little Owl, 90 Bedford St, which is close to several subway lines, making public transit a convenient option for most visitors.

Duration and timing: The tour lasts approximately 2 hours, starting at 1:30 pm, enabling you to fit it comfortably into a day of sightseeing.

What to wear: Since you’ll be walking outdoors, comfortable shoes are a must. Weather can vary depending on the season, so bring an umbrella or jacket if needed.

Drinks: While the tour includes visits to historic bars, drinks are paid for separately, so budget accordingly if you’d like to enjoy a beer or cocktail at some stops.

Accessibility: The tour is suitable for most people with moderate physical fitness. However, some venues might have steps or uneven floors, so keep that in mind if mobility is a concern.

Who Will Love This Tour

This experience is best suited for history enthusiasts, architecture buffs, or anyone intrigued by the shadowy side of New York’s past. If you enjoy stories about organized crime, political intrigue, or the social history of immigrant communities, you’ll find plenty to love. It’s also perfect for travelers who prefer walking tours over bus rides, as it offers an intimate look at the city’s historic neighborhoods.

Families with older children or teens who have an interest in American history may also enjoy the storytelling aspect. However, younger children might find the pace or content less engaging.

The Sum Up

The New York City Prohibition Walking Tour offers a well-rounded, authentic glimpse into the city’s clandestine past, blending history, architecture, and storytelling in a manageable two-hour walk. It’s a fantastic way to uncover stories of gangsters, speakeasies, and political corruption that shaped NYC’s gritty character, all while strolling through some of its most historic neighborhoods.

For travelers seeking a mix of education and entertainment, this tour delivers a unique perspective that’s both fun and insightful. The price is reasonable given the depth of stories and locations covered, making it a valuable addition to any NYC itinerary.

If you have an interest in urban history, prohibition-era crime, or historic bars, this tour is likely to become a memorable highlight. It’s especially ideal if you enjoy walking, storytelling, and discovering the city’s lesser-known stories that go beyond the usual tourist spots.

Frequently Asked Questions

Where does the tour start and end?
The tour begins at Little Owl, 90 Bedford St, and finishes at Pete’s Tavern, 129 E 18th St, providing easy access via public transportation.

How long does the tour last?
It lasts approximately 2 hours, giving you enough time to explore each stop without feeling rushed.

Can I buy drinks during the tour?
Yes, guests may purchase drinks at some stops, but these are paid for separately from the tour fee.

Is the tour suitable for all ages?
Most people with moderate physical fitness can participate. The tour is geared toward adults, especially those interested in history and architecture.

Are tickets included in the price?
Yes, admission to four historic saloons is included, allowing you to experience the venues firsthand.

What neighborhoods will I see?
You’ll explore Little Italy, Gramercy Park, and walk through historic streets that tell stories of NYC’s Prohibition days.

What is the group size?
The tour accommodates up to 40 travelers, ensuring a comfortable and engaging experience.

Is the tour accessible?
While generally suitable for most, be aware some venues may have stairs or uneven floors.

How do I cancel if needed?
Cancellation is free up to 24 hours before the tour, making it flexible if your plans change.

This walking tour promises a lively, authentic peek into New York City’s secretive past. Whether you’re a history buff, a curious traveler, or someone looking for a different perspective on NYC, it offers a memorable, informative experience well worth the modest fee.