NYC: Night Out Prohibition History Bar and Speakeasy Tour

NYC: Night Out Prohibition History Bar and Speakeasy Tour offers a lively, educational glimpse into the city’s spirited past. For $36 per person, you’ll spend about three hours wandering through Midtown’s most iconic bars and secret speakeasies, all while learning about the era when alcohol was outlawed and the city’s nightlife went underground. Led by a knowledgeable local guide, this tour combines history, culture, and a taste of New York’s vibrant nightlife.

What really makes this experience stand out are the insider privileges—like expedited entry and VIP treatment at each venue—and the engaging storytelling about immigration, politics, and the cultural shifts during Prohibition. Two things we love: first, the chance to visit three distinct venues, each with its own character—ranging from historic pubs to lively modern speakeasies. Second, the way the guide brings history to life with lively anecdotes, making the past feel immediate and relevant.

A possible consideration is that you’ll need to walk about 1.5 miles, so comfortable shoes are a must. Also, drinks are not included in the price, so be prepared to purchase beverages at each stop. This tour is best suited for those who enjoy a blend of history, storytelling, and socializing in a lively setting—perfect for curious travelers, first-timers in NYC, or anyone keen to experience the city’s nightlife with a historical twist.

Key Points

• Historical immersion: Learn about NYC’s Prohibition era through expert storytelling.
• VIP treatment: Expedited entry and insider service at each venue.
• Diverse venues: Visit three unique bars, ranging from historic pubs to modern speakeasies.
• Social experience: Meet travelers from around the world in a lively, friendly atmosphere.
• Authentic experience: Walk through iconic NYC sites while uncovering hidden gems.
• Value for money: For $36, you get a memorable evening with expert guidance and exclusive access.

You can check availability for your dates here:

Exploring the NYC Prohibition Night Out Tour

An Introduction to the Experience

If you’re curious about what made New York City’s nightlife so captivating during the 1920s, this tour offers an engaging way to explore that chapter. For three hours, we walk through Midtown, visiting three iconic bars—each with its own story and atmosphere—while a local guide like Ryan or Ariel shares insights that make history come alive.

At $36, this tour is a friendly price point considering the VIP access and the chance to skip long lines. It’s a lively, social outing that’s perfect for those interested in authentic, local experiences rather than sterile tourist spots.

Two aspects we really appreciate are the personal touches—like preferred entry—and the detailed storytelling, which adds depth to the usual pub crawl. A single drawback might be the walking—about 1.5 miles—so packing comfortable shoes is wise. Also, drinks aren’t included, so you should budget for beverages at each stop, which can be part of the fun.

This tour suits travelers who love history, enjoy social outings, or are eager to see a different side of NYC’s nightlife. It’s especially appealing to first-time visitors wanting to blend fun with education, or culture-savvy travelers seeking an authentic city experience.

Top Highlights of the Tour

• Visit three Midtown bars—from historic pubs to modern speakeasies—each with a distinct vibe.
• Learn stories about immigration and politics that shaped NYC’s culture during Prohibition.
• Enjoy VIP treatment—express entry and insider service—so you spend less time waiting.
• Meet a diverse group of travelers in a relaxed, social atmosphere.
• See some iconic NYC sights along the way, adding context to your night out.
• Taste the city’s nightlife without the hassle of planning or lines.

The Detailed Itinerary and What to Expect

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Meeting Point and First Impressions

You’ll meet your guide outside the One Worldwide Plaza building on 8th Avenue, a spot marked by a large American flag and a bike rack. From here, the adventure begins with a short walk through Midtown’s streets, a lively neighborhood that’s a perfect backdrop for uncovering NYC’s hidden bar culture.

First Stop: A Historic Midtown Pub

Your first venue typically offers an atmosphere straight out of the Roaring Twenties—perhaps with vintage décor and a warm, inviting vibe. Guests consistently comment on the friendly service and the stunning interiors that evoke that Prohibition-era charm.

One reviewer mentioned, “The 3 stops we made were all so different and really good in their own ways,” highlighting the variety of venues. At this first stop, you’ll get a chance to relax, chat with fellow travelers, and try some classic cocktails or beers for purchase.

Second Stop: Hidden Speakeasy

Next, you’ll venture into a concealed speakeasy, often hidden behind unassuming doors or behind secret entrances. These venues are where the true ‘undercover’ spirit of Prohibition lives on. Expect dim lighting, vintage décor, and an intimate atmosphere that transports you back in time.

Travelers often rave about the insider access: “We had such an amazing time… Ariel was friendly, funny and well prepared.” This stop illustrates NYC’s ingenious way of keeping nightlife alive during Prohibition, and you’ll get a taste of that resilience.

Third Stop: A Modern Twist on a Historic Venue

The final venue often blends historical elements with contemporary flair, offering a lively scene with modern cocktails or craft beers. It’s a perfect spot to unwind after walking and soaking in the city’s stories.

Guests frequently note the excellent service and interesting stories shared by guides, which make the experience all the more memorable.

Between Stops: City Sights and Stories

As you walk, your guide shares stories about immigration, political upheavals, and the cultural fabric of NYC during that era. You’ll see some iconic sites and discover hidden gems that are often overlooked by travelers.

End of Tour and Socializing

The tour concludes after three hours, often with an invitation to continue exploring or to hang out at a nearby bar. Several reviews mention how the group carried the night on afterward, emphasizing the social, friendly vibe.

Authentic Experiences and Why They Matter

What makes this tour stand out is the combination of history, culture, and social connection. Visiting three different venues not only breaks the monotony but also showcases NYC’s versatility—from historic to modern. The insider privileges like fast-track entry mean less waiting and more time enjoying your drinks and conversations.

The storytelling aspect is particularly engaging. For example, one reviewer notes, “Ryan was fun and made the whole tour a fabulous time,” which highlights how guides bring the past alive with humor and knowledge. You’ll leave with a deeper understanding of NYC’s immigrant waves, political changes, and how nightlife persisted against all odds.

Drinking and Budgeting

While drinks are not included, the prices at each venue tend to be reasonable, especially considering the VIP treatment. You might find cocktails costing around $10-15, but the experience of skipping lines and having a knowledgeable guide is well worth it.

Walking and Accessibility

With about 1.5 miles of walking spread across the evening, this tour is best suited for those comfortable on their feet. The dress code is upscale casual, so avoid flip-flops, shorts, or ripped clothing—venues require a neat appearance.

Who Should Consider This Tour?

This experience is ideal for travelers who want a blend of history and nightlife without the hassle of planning each visit. It’s perfect for first-timers in NYC eager to see Midtown’s hidden bar scene, or history buffs interested in the city’s Prohibition past. Social butterflies will appreciate the friendly group atmosphere and the chance to meet fellow travelers.

It’s also well-suited for adults over 21, as alcohol consumption is part of the experience. If you’re looking for a lively, educational night out with a local guide sharing fascinating stories, this tour offers excellent value.

Frequently Asked Questions

Do I need to bring my own drinks?
No, drinks are not included in the tour price, but you can purchase beverages at each venue.

Is this tour suitable for people with mobility issues?
You should be able to walk about 1.5 miles overall. Mobility scooters, large bags, or oversized luggage are not allowed, so consider your mobility needs before booking.

What should I wear?
Dress in upscale casual attire. Ripped clothing, flip-flops, tank tops, or sports jerseys are not permitted at the venues.

Can non-U.S. citizens participate?
Yes, but non-U.S. citizens need to bring a passport. U.S. citizens need valid ID.

When does the tour run?
Usually in the evening, and you can reserve the spot with free cancellation up to 24 hours before.

Is this a group tour?
Yes, typically a small group—making it intimate and friendly, with an average of 4-20 participants.

Final Thoughts

If you’re after a fun, informative, and social evening in New York, this tour hits all the right notes. It’s a smart choice for those curious about the city’s past, eager to skip lines and enjoy VIP treatment, and interested in authentic venues with stories to tell. The combination of history and lively nightlife makes for a memorable experience, especially in a city that has always been about reinvention and resilience.

Whether you’re traveling solo, as a couple, or with friends, this tour offers a window into the spirit of New York during one of its most fascinating eras—all wrapped up in a fun, walkable night out.

Ready to step back into the Roaring Twenties and see Midtown’s hidden side? This tour provides a lively mix of history, culture, and cocktails that makes for an unforgettable night in the city that never sleeps.

You can check availability for your dates here: