New York City: Prohibition Walking Tour – With Drinks

If you’re craving an engaging way to uncover New York City’s gritty past, this Prohibition Walking Tour offers a fascinating glimpse into the city’s underground speakeasies, gangster lore, and political corruption. Offered by Forty Thieves Tours, this two-hour journey combines history, storytelling, and a taste of the Prohibition era, all while wandering through some of the city’s oldest neighborhoods.

We particularly like the knowledgeable guides who make the stories come alive and the opportunity to sample a Prohibition-style cocktail or beer at each stop. On the downside, the tour is only suitable for those 21 and over and might not be accessible to everyone with mobility issues. Still, if you enjoy stories of the underworld mixed with a drink in hand, this tour is a superb pick for history buffs and curious travelers alike.

This experience suits those who appreciate authentic history over scripted narratives, people interested in New York’s criminal past, and anyone looking for a fun, social way to spend part of an afternoon.

Key Points

• Historic Saloons: Visit three of NYC’s oldest and most iconic watering holes, steeped in Prohibition lore.
• Authentic Drinks: Enjoy a Prohibition-style cocktail or beer at each stop, included in the ticket price.
• Storytelling: Learn about gangsters, bootleggers, and political figures linked to the city’s underworld, with engaging anecdotes.
• Tammany Hall Connection: Discover how organized crime and political corruption intertwined during the Prohibition era.
• Expert Guides: Well-reviewed guides make the stories vivid and add a personal touch to the experience.
• Legendary Finale: End at a famous saloon with a final toast, appreciating the city’s legendary past.

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An In-Depth Look at the Tour Experience

The tour begins at the Great Hall of Cooper Union, a historic site positioned conveniently in Manhattan. From there, your guide, Earl, or another knowledgeable host, leads you through quaint streets lined with historic buildings. You’ll quickly notice this is more than just a drinking tour; it’s a history lesson infused with local stories, colorful characters, and a bit of NYC’s rebellious spirit.

What You’ll Visit

The three historic saloons are more than just places to grab a drink—they’re living relics of a time when speakeasies operated in shadows, and mobsters like Al Capone’s American counterparts ruled the underworld. These venues have hosted some of the most notorious criminals and political power brokers, making each stop a window into a grittier, more secretive past.

While the exact names of the saloons aren’t specified, what’s clear is that each has its own story to tell—stories your guide will bring to life with a mixture of humor and insight. The stops are chosen carefully to maximize the experience, combining authentic ambiance with historical significance.

What’s Included

Each stop includes a drink, either a Prohibition-style cocktail or a beer, giving you a taste of what patrons might have enjoyed during the era. This inclusion elevates the tour from just a walk to a social experience, encouraging conversation and camaraderie among the group.

The guides are praised for their depth of knowledge. One reviewer mentioned Earl as “fantastic,” highlighting his ability to make history feel relevant and fun. Another reviewer described the tour as like “going to old bars with a friend,” emphasizing the relaxed and friendly atmosphere.

The Stories and Atmosphere

The tour’s appeal lies in its storytelling. You’ll hear about gangsters and bootleggers who cornered the illegal alcohol trade, and the political scandals linked to Tammany Hall—the infamous political machine. These stories aren’t just for entertainment; they help us understand how crime and politics intertwined to shape NYC’s identity.

While the tour emphasizes the underworld, it also offers a look at the cultural significance of these establishments. Many of these saloons served as meeting places for influential figures who shaped the city’s history, making each visit a peek into a secret world that still influences NYC today.

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Final Stop and Endnote

The tour wraps up at a legendary saloon, a true NYC institution. Here, you’ll enjoy a final drink and reflect on the stories you’ve heard. The ending is designed to leave you with a deeper appreciation of NYC’s complex past—beyond the bright lights and tourist sights.

Practical Details and Value

At $89 per person, the tour offers good value, especially considering the three included drinks and the intimate, guided storytelling. The duration of two hours makes it a manageable outing that fits well into an afternoon or early evening slot.

The meeting point at Cooper Union’s Great Hall is easy to find and steeped in history itself, adding an extra layer of authenticity to the experience. The tour is limited to those 21 and older—a necessary restriction given the nature of the content and alcohol consumption.

While the group size isn’t specified, reviews suggest that guides like Earl provide personalized attention, making the experience feel more like a friendly exploration than a crowded bus tour.

Comfortable shoes are recommended, as walking is involved, and the streets of NYC can be uneven. It’s also wise to arrive 15 minutes early to meet your guide and get settled before starting the tour.

Who Would Enjoy This Tour?

This tour is ideal for history lovers eager to uncover NYC’s dark past. It’s also perfect for local fans wanting to explore familiar neighborhoods through a different lens, or first-time visitors seeking an engaging, narrative-driven activity.

If you enjoy stories of crime, political intrigue, and social history, you’ll find plenty to love here. However, it’s important to note that the tour isn’t suitable for those with mobility limitations or anyone under 21, due to the venue restrictions and alcohol component.

The Sum Up

The Prohibition Walking Tour—With Drinks offers a lively, authentic look into New York City’s shadowy past. With knowledgeable guides, delicious drinks, and hidden stories, it’s a compelling way to connect to the city’s history beyond the typical tourist sights.

Perfect for those who like their history served with a side of social fun, this tour combines storytelling, a bit of adventure, and a taste of the city’s rebellious spirit. It’s a great fit for curious travelers who enjoy immersive experiences and aren’t afraid to walk the streets that once hosted the city’s most notorious figures.

While not suited for everyone, especially those with mobility issues or underage visitors, it delivers a memorable slice of NYC history packed with personality and charm. If you’re interested in a fun, informative, and uniquely NYC experience, this tour deserves a spot on your list.

FAQs

Is this tour suitable for people with mobility issues?
No, it’s not recommended for those with mobility limitations, as it involves walking through city streets and historic venues.

Are drinks included in the ticket price?
Yes, you’ll receive one Prohibition-style cocktail or beer at each of the three saloons, included in the $89 fee.

Do I need to bring my ID?
Yes, since the tour is for those 21 and over, a valid ID or a copy is required.

Where does the tour start?
The meeting point is at the Great Hall of Cooper Union, a historic and central location in Manhattan.

How long does the tour last?
It lasts about two hours, making it a perfect afternoon or early evening activity.

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

This Prohibition Walking Tour combines entertainment, education, and a bit of NYC’s rebellious past—an experience that’s as flavorful as the drinks you’ll enjoy along the way.

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