New York City Prohibition Walking Tour

Exploring the New York City Prohibition Walking Tour

When it comes to experiencing New York City’s vibrant past, especially the clandestine days of Prohibition, there are few better ways than a guided walk through some of its historic neighborhoods and legendary bars. While we haven’t personally taken this tour, it’s a well-reviewed and thoughtfully designed experience that offers a glimpse into the gritty, rebellious side of NYC’s history.

What we really like about this tour is how it combines storytelling with authentic places — visiting four historic saloons and key spots that played a role in organized crime and political intrigue. It’s a solid choice for travelers interested in history, architecture, and the tales behind iconic city landmarks. One possible limitation is the tour’s focus on history rather than modern-day nightlife, so if you’re looking for a lively bar crawl, this may not be your best fit.

This tour works particularly well for those who enjoy history, architecture, and stories of gangsters, bootleggers, and political corruption. If you’re curious about the underground side of NYC and want to see historic bars that have survived nearly a century of change, this tour’s a good pick.

Key Points

• Authentic Historic Venues: Visit four of NYC’s oldest and most iconic saloons, each with its own story.
• Narrative Focus: Learn about Prohibition, gangsters, and political figures like Tammany Hall through engaging storytelling.
• Flexible Experience: Optionally purchase drinks at some stops to enhance the experience.
• In-depth Stories: Inside stories from legendary staff and tales of notorious figures bring history to life.
• Short & Manageable: About 2 hours long, offering a compact but rich historical overview.
• Affordable Value: At $47.20, it’s a reasonably priced way to gain a deeper understanding of New York’s secretive past.

A Close Look at the Tour Itinerary

Start at McSorley’s Old Ale House

The tour kicks off at McSorley’s Old Ale House, one of New York’s oldest surviving saloons, established in the 19th century. As you step inside, you’re immediately transported to a different era with its rough-hewn wooden interiors and historic ambiance. Your guide will share stories from Prohibition times, highlighting McSorley’s role as a gathering spot for gangsters, bootleggers, and political figures.

You’ll hear about how this bar managed to remain open through prohibition despite the crackdown on alcohol, making it a tangible link to the past. The visit lasts about 25 minutes, and admission is included, so you get to explore without worrying about extra costs. Travelers often comment on the charm of this historic spot, with some noting that “the stories really add to the atmosphere,” and that standing in a place that’s been around for over a century makes history feel alive.

Walk through Little Italy

Next, the tour meanders through Little Italy, a neighborhood famous for its immigrant roots and vibrant street life. As you stroll, your guide explains the neighborhood’s transformation during Prohibition, when illegal speakeasies thrived within its narrow streets. This part of the tour is free, giving you a chance to absorb the sights and sounds of an iconic NYC enclave.

You might find that this walk offers some excellent photo opportunities, with colorful signage and historic architecture. It’s also an educational moment — learning how the immigrant communities adapted and kept their traditions alive in the face of prohibition-related challenges.

Stop at the Old Town Bar

The next stop is Old Town Bar, known for its preserved interiors that date back to the early 20th century. This spot offers a vivid glimpse into Prohibition-era drinking culture, with stories of notable figures who frequented its historic counters. The bar’s long-standing reputation (admission included) makes it a highlight for history buffs and architecture enthusiasts alike.

Guests often mention the “authentic feel,” with some appreciating the chance to “sit at the same bar where bootleggers once plotted.” The guide’s inside stories about gangsters and political figures make this a memorable part of the tour.

Explore Gramercy Park

Moving to Gramercy Park, the tour discusses its role in political movements and its connection to Prohibition-era New York. Though a smaller part of the experience, the park offers some peaceful views amidst the city’s hustle. The guide explains the neighborhood’s significance, tying it into broader themes of political corruption and reform.

Though the visit here is brief at around 15 minutes and free to explore, it’s a nice breather and an opportunity to consider how these historic districts played a part in NYC’s Prohibition story.

Final stop at Pete’s Tavern

The tour concludes at Pete’s Tavern, one of NYC’s oldest continuously operating bars. This historic spot has hosted many famous patrons and is famed for its secret Prohibition-era stories. At around 20 minutes, this stop wraps up the experience with a sense of continuity and tradition.

Guests can relax, take photos, and hear stories about the bar’s enduring legacy. Many reviewers appreciated this ending, with comments like “the stories about Prohibition secrets make it a fitting finale.”

What’s Included and What’s Not

This tour covers visits to four historic saloons, all with their own stories and atmospheres, along with inside tales from legendary staff. You’ll learn about gangsters, bootleggers, Tammany Hall, and the speakeasy era — all crucial elements of New York’s underground history.

While the admission to each site is included, drinks are not. Guests have the option to purchase beverages at any stop, which adds a personal touch and allows for a more immersive experience if desired.

The tour begins at Little Owl and ends at Pete’s Tavern, with a convenient starting time of 1:30 pm. It’s designed for those with moderate physical fitness, since it involves some walking and standing.

Practical Details

The price point of $47.20 per person offers good value, considering the inside stories, guided commentary, and access to historic venues. Since the tour lasts about two hours, it’s a manageable amount of time for those looking for a focused, informative experience.

Meeting near public transportation makes it easy to access, and with a maximum group size of 40, it’s intimate enough for questions and engagement. The free cancellation policy provides peace of mind in case your plans change.

Why Choose This Tour?

If you’re fascinated by organized crime, political corruption, and hidden NYC history, this walk offers a compelling glimpse into that world. It’s especially suited for travelers who prefer storytelling and historic ambiance over pub-hopping. The mix of historic buildings, legendary tales, and authentic interiors makes it a memorable way to spend a couple of hours exploring New York’s rebellious past.

For families, history buffs, or curious travelers, this tour provides a rich, contextual understanding of how Prohibition shaped the city. It’s an opportunity to see parts of NYC that have survived nearly a century, with stories that still resonate today.

FAQs

Is this tour suitable for all ages?
The tour is generally suitable for adults and older teenagers interested in history and stories of organized crime. Younger children might find some of the stories less engaging.

Are drinks included in the tour?
Drinks are not included; guests may purchase beverages at some stops if they wish to enhance their experience.

How long does the tour last?
The tour lasts approximately 2 hours, covering five stops with walking in between.

Where does the tour start and end?
It begins at Little Owl on Bedford Street and ends at Pete’s Tavern on East 18th Street.

Is the tour accessible by public transportation?
Yes, the meeting point is near public transit, making it easy to reach without a car.

Do I need to be in good physical shape?
Yes, travelers should have a moderate level of physical fitness as the tour involves walking and some standing.

Can I cancel this tour?
Yes, you can cancel up to 24 hours in advance for a full refund, thanks to the free cancellation policy.

Final Thoughts

This Prohibition Walking Tour offers an engaging, authentic peek into New York City’s shadowy past, combining historic saloons with lively stories of gangsters and political intrigue. For those interested in urban history, architecture, and hidden stories, it’s a well-priced experience that balances education with entertainment.

Perfect for history enthusiasts or curious travelers wanting to understand the city’s gritty side, this tour provides a memorable snapshot of a rebellious era that still influences NYC today. Whether you’re a first-time visitor or a seasoned New Yorker, the tales behind these legendary venues add depth and character to your city experience.

If you’re eager for stories of speakeasies, gangsters, and political corruption, and enjoy exploring historic bars with a knowledgeable guide, this walk is a great pick. Just remember to bring your curiosity and maybe a dollar or two for a drink — or at least to tip your guide!