NYC: Night Out Prohibition History Bar and Speakeasy Tour

If you’re looking to combine history, culture, and a bit of nightlife on your trip to New York City, this Night Out Prohibition History Bar and Speakeasy Tour offers an engaging way to do all three. Spanning approximately three hours, this guided experience takes you through some of Midtown Manhattan’s most iconic and hidden drinking spots—places that once thrived during the Prohibition era and continue to captivate visitors today.

What we love about this tour is how it balances storytelling with access. You’ll get expedited entry into each venue, meaning less waiting and more enjoying your drinks and conversations. Plus, the tour’s guides are praised for their knowledge, making the history of NYC’s underground bar scene as vivid as the drinks you’ll sip. That said, it’s worth noting that the tour involves walking around the city and visiting multiple venues, so comfortable shoes and a decent level of stamina are advisable.

One consideration is that drinks are not included in the ticket price, so you’ll want to budget accordingly if you plan to sample cocktails at each stop. This tour appeals most to those who love a good story, enjoy exploring authentic local spots, and want a relaxed yet educational night out in the city.

• Authentic Experience: Combines history, storytelling, and nightlife in a fun, relaxed way.
• Expert Guides: Knowledgeable hosts like Aerille, Jack, and Sarah bring the stories of NYC’s Prohibition days to life.
• Access & Convenience: Priority entry at each venue means more time for drinks and socializing.
• Variety of Venues: Mix of historic speakeasies, modern bars, and iconic Midtown pubs.
• Walking Tour: Approximately 1.5 miles of walking through Midtown, so wear comfortable shoes.
• Flexible & Value-Driven: Good balance of cost ($36) versus the experience, especially with the insider treatment.

Starting Point and Meeting Logistics

The tour kicks off at 825 8th Ave, outside the One Worldwide Plaza building—an easily recognizable spot with a large American flag and a bike rack out front. Meeting in the heart of Midtown means you’re in the middle of some of NYC’s most lively streets, and it’s a great jumping-off point for exploring the city afterward.

The meeting spot’s central location means you won’t need additional transportation unless you’re arriving from further afield. The tour is designed for those who enjoy a bit of urban exploring, as it involves walking around 1.5 miles over the course of the evening. Participants should plan to arrive ready to walk, with comfortable footwear and a passport or ID for check-in.

The Itinerary & Venues

Stop 1: The Starting Location
The tour begins with an overview of NYC’s history, setting the stage for the subsequent visits. Although specific venues for each stop aren’t listed in detail, you’ll be visiting three iconic bars, pubs, lounges, or speakeasies in Midtown, some of which are hidden or historic establishments. The first venue often offers a warm-up with a classic cocktail or a signature drink, setting the tone for the evening.

Stop 2: Midtown Hidden Gems & Historic Pubs
This is where the tour’s storytelling shines. Guides like Aerille, Jack, and Sarah are praised for their engaging narratives. You’ll learn about how immigration, politics, and societal shifts shaped NYC’s bar scene, especially during the Prohibition era. Reviewers mention that the venues themselves are stunning, with various styles—from authentic speakeasies to modern reinterpretations—offering a glimpse into the city’s layered past.

Stop 3: Finish at Times Square
The tour wraps up back near Times Square, giving you the perfect shot of the city’s bright lights and energy to end your night. This is a popular spot for photos and a chance to soak in the vibrant atmosphere after a night of history and drinks.

What You’ll Experience at Each Venue

Guests report that they receive preferred customer treatment—expedited entry and attentive service, which makes the experience more relaxed and enjoyable. At each stop, you’ll have opportunities for a drink (though not included in the ticket price, so be prepared to purchase cocktails or beers). Reviewers mention that drinks can run around $20 each, so budgeting for extra spending is wise, especially if you want to sample a few signature cocktails.

The venues are praised for their stunning architecture and ambiance, with some being historic buildings that once served as key parts of the underground bar scene. The stories told by guides make the experience richer—learning about the immigration waves that brought diverse communities to NYC or the resilience of local businesses during Prohibition adds depth to the visit.

The Guides & Their Stories

Guests repeatedly praise the guides for their knowledgeability and engaging storytelling. For example, Aerille’s enthusiastic narration keeps everyone interested, answering questions about NYC’s social changes and the history of each venue. Hannah describes her guide as “knowledgeable and lovely,” while Deborah highlights how Aerille answered all questions, adding extra value to the experience.

Another reviewer, Jessica, raves about Laurie, calling her “the best guide,” and mentions that her helpfulness and energetic style made the night memorable. The guides do more than just lead—they weave a narrative that makes each venue come alive.

The Social Aspect & Group Dynamic

This tour isn’t just about drinking; it’s about meeting people from around the world while sharing in a common interest. Many reviews mention the fun, friendly atmosphere created by the guides and fellow travelers. It’s suitable for solo travelers, couples, or groups of friends looking for a relaxed yet fascinating night out.

Because it’s a small group, you get personalized attention, and the insider treatment at each venue means fewer lines and more time to enjoy each drink. The tour’s social vibe, combined with the stories, encourages conversations and connections.

Pros:

• Authentic, well-curated venues with both historic and modern appeal
• Engaging guides with deep knowledge of NYC’s Prohibition and immigrant history
• Priority entry at each venue ensures a smooth experience
• Affordable price point considering the access, storytelling, and small-group atmosphere
• Great for history buffs and those curious about NYC’s underground pub scene

Cons:

• Drinks are not included, so additional costs can add up
• The walking distance, while manageable, requires comfortable shoes and some stamina
• Limited to people over 21, so not suitable for minors or families
• The tour only covers Midtown, so those seeking a broader city experience may find it narrow

This experience appeals most to history enthusiasts, nightlife lovers, and travelers eager for authentic local experiences. If you enjoy storytelling, discovering hidden spots, and learning about the city’s past in a relaxed environment, this tour is a perfect fit. It also works well for those celebrating special occasions—like a birthday—since the venues often impress with their ambiance and history.

It’s especially suitable for travelers with a moderate budget who want value beyond just drinks—they’re paying for access, insider storytelling, and a unique perspective on NYC’s vibrant nightlife.

The NYC Night Out Prohibition History Bar and Speakeasy Tour offers a genuinely immersive way to explore the city’s nightlife through the lens of its past. With knowledgeable guides, exclusive access, and a variety of historic venues, it’s a smart choice for those interested in a fun, educational, and social evening.

While it’s not a pub crawl in the traditional sense—there’s a focus on storytelling and history—your experience will be enriched by the stunning venues and the stories behind them. Expect a relaxed pace, plenty of fascinating insights, and a chance to see Midtown Manhattan from a different angle.

This tour is best suited for curious travelers who want to combine a bit of learning with their evening out, especially if they appreciate history, architecture, and authentic local flavor. If you’re after a memorable, well-rounded night in NYC that balances fun with education, this experience is hard to beat.

Do I need to book in advance?
Yes, booking in advance is recommended to secure your spot, especially during peak travel seasons. You can reserve now and pay later, offering flexibility.

How long does the tour last?
The tour lasts for about 3 hours, which includes visiting three different venues and walking through Midtown.

Are drinks included?
No, drinks are not included. You’ll have the opportunity to purchase beers, cocktails, or other beverages at each stop, typically costing around $20 each.

What should I bring?
A passport or valid ID is required for check-in, as is comfortable walking shoes for the approximately 1.5 miles of walking involved.

Is the tour suitable for non-U.S. citizens?
Yes, non-U.S. citizens should bring their passports, but the tour is open to all over 21.

Can I join if I’m traveling solo?
Absolutely. Many guests join solo and enjoy the social atmosphere, often making new friends along the way.

This tour offers a perfect blend of history, culture, and lively NYC nightlife, making it a memorable addition to your city visit.