The NYC Speakeasy Adventure: A Tipsy Trip Through History

If you’re looking to add a touch of mystery and vintage charm to your New York City visit, the NYC Speakeasy Adventure offers a lively, history-rich experience you won’t forget. This guided tour takes you behind the scenes of Midtown Manhattan, Hell’s Kitchen, and the Theatre District, revealing some of the city’s best-kept secrets—hidden bars that once thrived during Prohibition. It’s a fun blend of storytelling, socializing, and authentic cocktails, perfect for those who love history with a dash of nightlife.

What makes this tour stand out? First, the expert guides bring the Prohibition era to life with captivating stories and anecdotes, making history feel immediate and personal. Second, the group-friendly atmosphere and preferred entry at each venue help keep things smooth and comfortable. However, one thing to keep in mind is that the tour runs about 3 hours and covers roughly 1.5 miles on foot, so it’s best suited for those comfortable with moderate walking and standing.

This adventure is ideal for history buffs, curious travelers, and nightlife enthusiasts who enjoy exploring with a small group. It’s also a good pick for those interested in NYC’s immigrant past, as the stories often weave in cultural insights. Just note, guests must be 21 and over, and the dress code leans toward “classy,” so come prepared to look sharp.

Key Points

• Historic focus: Learn about the Prohibition era and NYC’s immigrant past through engaging stories.
• Exclusive access: Enjoy express entry and preferred treatment at three secret speakeasies.
• Social experience: Meet fellow travelers while browsing some of NYC’s hidden gems.
• Flexible: Tour duration is 3 hours, with options to purchase drinks and food during stops.
• Walking tour: Covers about 1.5 miles, making it manageable but still requiring comfortable shoes.
• Affordable: Priced at $30 per person, offering a good value for the experience and access.
• Age requirement: Must be 21+ to join the tour and purchase drinks.
• No wheelchair access: Not suitable for guests with mobility issues.
• Booking: Flexible cancellation up to 24 hours in advance; pay later option available.

The NYC Speakeasy Adventure is a thoughtfully curated experience that balances historical storytelling, social interaction, and the thrill of discovering hidden NYC locations. It’s not just about drinking; it’s about understanding a fascinating chapter of American history that still influences the city’s nightlife today.

You can check availability for your dates here:

Starting Point and Logistics

The tour begins outside the entrance to One Worldwide Plaza, located on 8th Avenue between 49th and 50th Streets. The meeting spot is straightforward, with clear signage — Carnegie Diner is across the street, and a bike rack marks the spot. Meeting here is convenient for travelers staying in Midtown, and the group’s small size keeps things intimate. The tour usually takes place in the evening, making it an ideal way to kick off a night out or wind down after a day of sightseeing.

Express entry at each venue means you skip the lines, which is a real bonus in busy NYC. The guides from TellTaleTours are in charge, ensuring everything runs smoothly and that you get the most out of your time.

The Itinerary: Three Secret Bars in Three Hours

The heart of the experience is visiting three historic bars and secret speakeasies. Each spot is carefully chosen for its ambiance, history, and authenticity. While the exact names aren’t listed, you can expect venues that still retain the clandestine vibe of the Prohibition era—hidden behind unassuming doors, with vintage decor and a lively yet intimate atmosphere.

First Stop: Midtown Manhattan

Here, you’ll likely encounter a bar that once served as a haven for city dwellers craving a clandestine drink. The guide shares stories of how these establishments operated under the radar, often run by immigrants seeking safe spaces during challenging times. You’ll get a sense of the city’s resilience and ingenuity through storytelling that makes history feel immediate.

Second Stop: Hell’s Kitchen

This neighborhood burst with life during Prohibition, and the second venue reflects that energy. Expect a place with authentic decor, perhaps with hints of the jazz age, and a tone of camaraderie among patrons. It’s a chance to appreciate how NYC’s diverse communities created vibrant nightlife even during restrictive times.

More Great Tours Nearby

Third Stop: The Theatre District

The final bar often has a theatrical flair, nodding to NYC’s entertainment roots. These venues offered a perfect setting for secret meetings and lively conversations. The stories shared here might include tales of famous figures who frequented these hidden spots, adding a layer of glamour and intrigue.

Each stop lasts around 30–40 minutes, giving you time to absorb the ambiance, chat with your guide, and enjoy the atmosphere. Drinks and food are available for purchase, with prices ranging from $18 to $28, so budget accordingly if you want to indulge.

The Guide and Stories

Guests consistently mention how much they appreciate the knowledge and enthusiasm of the guides. One reviewer lauded Katherine for her “amazing stories, laughs, and great drink recommendations,” emphasizing how her storytelling kept everyone engaged. Another mentioned how the guide Rory made the history engaging, blending facts with humor and local insights.

The stories are a highlight—covering everything from the immigrant experience that shaped NYC’s drinking scene to the clandestine operations that kept the city’s nightlife alive during Prohibition. This context enriches the experience, making the visit more than just a pub crawl; it becomes a window into a tumultuous and inventive time in NYC’s past.

The Social Aspect and Atmosphere

One big draw for many guests is the friendly, sociable environment. The small group size (usually around 10-12 people) fosters conversations and a sense of camaraderie. People frequently mention how the tour becomes a shared adventure, with new friends made over cocktails and stories.

The venues themselves often have stellar vibes—vintage decor, dim lighting, and a warm, welcoming feeling that transports you back to the 1920s. It’s a chance to see a side of NYC that few travelers get to experience, all while enjoying some of the city’s best classic cocktails.

The Practical Side: Cost and Comfort

At only $30, this tour offers fantastic value, considering the exclusive entry and guided storytelling. While drinks are not included in the price, the options are reasonably priced, and the experience of visiting these hidden spots makes it well worth the additional expense. The tour’s 3-hour duration balances enough time to enjoy each venue without feeling rushed.

Comfort-wise, the walk covers about 1.5 miles, mostly in urban neighborhoods, so comfortable shoes are advisable. Since the tour is not wheelchair accessible, travelers with mobility concerns should consider this before booking.

Who Should Consider This Tour?

This adventure is perfect for adults who love history, nightlife, or both. It’s especially appealing to those interested in NYC’s immigrant past and Prohibition-era stories. If you enjoy guided experiences with engaging storytellers, this tour will satisfy your curiosity. It’s also a great choice for groups wanting a fun, social evening with a dash of education.

However, it’s not suitable for those under 21 or visitors with mobility issues, as the tour involves some walking and the venues are not wheelchair accessible.

Final Thoughts on Value and Experience

For just $30, the NYC Speakeasy Adventure offers an immersive glimpse into a lively chapter of city history. The combination of expert guides, exclusive access, and authentic venues makes it a standout activity for those seeking a memorable night out. It turns a typical pub crawl into a storytelling journey, making history feel fun and immediate rather than dusty and distant.

The small group setting, engaging stories, and vintage vibes combine to create a balanced experience—informative but relaxed, social but immersive. It’s a fantastic way to see a different side of Manhattan, one that’s full of secrets, stories, and spirits.

Who Will Love It?

This tour suits travelers who enjoy a mix of history, culture, and nightlife. If you’re a curious explorer who appreciates authentic experiences and doesn’t mind a bit of walking, you’ll find it both entertaining and enlightening. It’s especially perfect for those interested in NYC’s immigrant roots and the colorful past that shaped its bars and neighborhoods.

In summary, if you want an engaging, storytelling-driven look at NYC’s Prohibition past, combined with the fun of discovering hidden bars, this tour hits the mark. Just remember to dress sharp, bring your ID, and prepare for an evening full of stories, camaraderie, and perhaps a spirited toast or two.

Is this tour suitable for all ages?
No, guests must be 21 or older to join and purchase drinks.

How long does the tour last?
It runs for about 3 hours, including visits to three different speakeasies.

What is the tour’s walking distance?
The route covers approximately 1.5 miles, mostly on city streets, so comfortable shoes are recommended.

Are drinks included?
No, drinks and food are available for purchase at each stop, with prices typically between $18 and $28.

Is the tour accessible for wheelchair users?
No, the tour is not wheelchair accessible.

What should I wear?
Classy attire is recommended to match the vintage, sophisticated vibe of the venues.

Can I cancel or reschedule?
Yes, you can cancel up to 24 hours in advance for a full refund, and booking allows for flexible payment options.

Where do I meet the guide?
Outside the entrance to One Worldwide Plaza on 8th Avenue between 49th and 50th Streets, near Carnegie Diner.

Is this tour offered in languages other than English?
No, it is conducted in English only.

What makes this tour worth it?
The combination of storytelling, exclusive access, and unique venues delivers an authentic slice of NYC’s past at a very reasonable price.

You can check availability for your dates here: