Speakeasy Drinks and Prohibition History Tour NYC

If you’re a history buff, a cocktail lover, or just someone curious about New York’s secretive past, this Speakeasy Drinks and Prohibition History Tour promises an engaging journey through Midtown Manhattan’s hidden bars and lively streets. While I haven’t personally taken this tour, reviews paint a picture of a well-curated, fun, and educational experience that combines history, good drinks, and small-group intimacy.

What we love about this tour is its focus on authentic speakeasy atmospheres, the knowledgeable guides who bring history to life, and the chance to savor some great cocktails in secretive, vintage-style venues. The only potential snag is that drinks are at your own expense, which might bump up the cost if you’re not careful. This tour seems best suited for those wanting a blend of history, lively nightlife, and a taste of old New York in a manageable 3-hour outing.

Key Points

• Authentic Experience: Visit three historic bars that embody the spirit of the Prohibition era.
• Expert Guides: Knowledgeable guides share compelling stories about bootlegging, the Gilded Age, and NYC’s clandestine nightlife.
• Convenient & Flexible: Several start times available, ideal for fitting into a busy sightseeing schedule.
• Cost & Value: Price is $36 per person, with drinks purchased separately, making it a flexible experience.
• Group Size: Limited to 16 travelers, creating an intimate and personalized atmosphere.
• Walking Tour: About 3 hours of light walking through Midtown, with some stops in iconic neighborhoods.

An Introduction to the Experience

This tour offers a chance to explore Midtown Manhattan through the lens of the Prohibition period, a time when alcohol was banned but underground bars thrived. It isn’t just about drinking—though you’ll sample cocktails at each venue—it’s also about understanding the culture, stories, and secretive nature of the era.

What’s appealing is the combination of walking, history, and nightlife, all led by a licensed local guide. Many reviews praise guides like Ariel, Katherine, Ryan, and Walter for their friendly, engaging storytelling and impressive knowledge of New York’s hidden past.

The Itinerary Breakdown

Starting Point: 825 8th Ave

Your journey begins here, where the guide gathers the group, ensuring everyone feels comfortable and ready to explore. This location is near public transportation, making it easy to meet up without hassle. The tour lasts roughly 3 hours, which is perfect for those wanting an engaging but not overwhelming experience.

Midtown & Times Square

From the meeting point, you’ll walk through Midtown Manhattan—famous for its towering skyscrapers, bustling streets, and the bright lights of Times Square. This walk sets the scene for the contrast between the city’s modern vibrance and its clandestine past. One reviewer noted that Walter, the guide, made the walk fascinating, sharing stories of the Gilded Age and how NYC’s elite once danced through prohibition with secret cocktails.

Historic Neighborhoods & Broadway District

Next, the tour meanders through historic neighborhoods, including the Broadway theater district. You’ll get a sense of how entertainment venues and nightlife evolved under the influence of Prohibition. Several reviews mention that guides like Katherine and Ariel bring this history alive, sharing fun and fascinating stories about bootleggers and the city’s underground bars.

Visiting the Bars

The core of this experience is visiting three bars or speakeasies, each with its own unique charm. These are not your typical tourist spots—they’re authentic, often tucked away behind unassuming doors, and exude vintage charm.

• First Venue: You might find yourself in a prohibition-style bar with memorabilia, vintage decor, and a relaxed ambiance. Reviewers describe this as a place that would be almost impossible to find on your own.
• Second Venue: Expect a private, intimate room, possibly with historical decor like velvet curtains or memorabilia from the era. One reviewer was blown away by the fact that the curtain in one venue was the actual set piece from “The Phantom of the Opera.”
• Final Venue: Usually a lively bar with a sense of history and character, where you can chat comfortably and enjoy your drinks. Some reviews mention that the last stops feel more like modern bars but still retain a speakeasy vibe.

Drinks & Atmosphere

All drinks are purchased separately, but guides are excellent at recommending cocktails based on your preferences. It’s worth noting that some guests found the drinks at the last stop weren’t their favorites, but the ambiance and experience more than compensated. Many reviewers remark on the quality of the guides’ storytelling and the hidden gems they uncovered.

The Guides & Stories

Several reviewers highlight the enthusiasm and deep knowledge of guides like Ryan, Ariel, Katherine, and Walter. They don’t just recite facts—they weave stories of bootleggers, Gilded Age elites, and the secretive bars of NYC, making history feel alive. One reviewer noted Ariel’s “wonderful storytelling,” while another praised Katherine for sharing her perspective as a native New Yorker.

Group Size & Atmosphere

With a maximum of 16 travelers, the tour maintains a friendly, engaging vibe. Many guests appreciated the intimacy, especially solo travelers or small groups, as it allowed for genuine conversations and personalized recommendations. One reviewer pointed out that with only one other person on the tour, they felt like they could really connect with the guide and learn more.

Walking & Duration

The three-hour duration is just right for a leisurely yet immersive experience. The walk covers key locations in Midtown and the theater district, with light physical activity involved. The reviews suggest that most participants found the pace comfortable, even for those with moderate fitness levels.

Cost & Value

At $36 per person, excluding drinks, this tour offers good value for those interested in both history and nightlife. The ticket price includes priority entry and storytelling, which can make all the difference in busy venues. The cost of drinks varies, but many find that the experience of uncovering hidden bars and learning local stories justifies the expense.

Unique Highlights & Guest Insights

• Guests love the authenticity of the venues; many felt like they had stepped back in time.
• The guides’ storytelling is often praised as engaging, humorous, and informative.
• The variety of venues—from private rooms to lively bars—keeps the experience fresh.
• Some mention that the last stops are more like modern bars, but still maintain an old-world charm.

Practical Tips for Visitors

• Book early; the tour is popular and often booked 26 days in advance.
• Dress upscale casual; no ripped clothing or sportswear permitted.
• Bring photo ID (passport for non-U.S. citizens) to verify age.
• Be prepared to purchase your drinks separately; budget accordingly.
• The tour is suitable for travelers with moderate physical fitness and those who enjoy walking and exploring.

This experience offers more than just sipping cocktails; it’s a glimpse into the clandestine side of NYC’s past. Whether you’re a history enthusiast, a nightlife explorer, or someone wanting a memorable night out with friends, this tour hits the mark. The guides’ stories, the hidden venues, and the lively atmosphere make for a truly unique adventure.

If you’re someone who appreciates authentic local spots, well-informed storytelling, and the thrill of discovering secret places, this tour is well worth it. The small group size ensures you won’t feel lost in the crowd, and the flexible start times make it easy to fit into a busy sightseeing schedule.

This speakeasy tour provides a perfect mix of history, entertainment, and socializing. The fact that many guests return for repeat visits, or recommend it as a must-do in NYC, speaks volumes about its appeal. It’s a fantastic way to experience the city’s underground nightlife, learn about its colorful past, and enjoy some delicious cocktails in a lively, intimate setting.

While drinks are extra and some venues may lean more towards modern bars than authentic speakeasies, the overall experience remains authentic and engaging. It’s especially suited for solo travelers, small groups, or couples who want a guided night out that combines storytelling with fun.

How long does the tour last?
The tour is approximately 3 hours, including walking between venues and time spent at each bar.

Where does the tour start?
It begins at 825 8th Ave, near public transportation, making it easy to access.

Are drinks included in the price?
No, drinks are purchased separately at each bar; the ticket price covers the guided experience and priority entry.

Is the tour suitable for all ages?
No, the minimum age is 21, and valid photo ID is required.

What should I wear?
Upscale casual attire is recommended; no sportswear or ripped clothing allowed.

Can I change the start time?
Several start times are available, but changes less than 24 hours before cannot be accepted.

Is this a walking tour?
Yes, it involves about 3 hours of walking, mostly through Midtown and theater districts.

How many people are in a group?
The tour is limited to 16 travelers for a more personal experience.

What if I have dietary restrictions or allergies?
Since drinks are purchased at venues, you can specify preferences or restrictions when guided.

This tour offers a lively and educational peek into New York City’s spirited past. If you’re eager to combine history with nightlife, appreciate the art of storytelling, and enjoy discovering hidden gems, it’s a fantastic pick. The small-group format and passionate guides make it a memorable evening worth the price for many travelers. Just remember to budget for drinks, dress smart, and prepare for a fun, immersive walk through NYC’s secretive Prohibition days.