The Secret Speakeasies and History Experience!

Traveling through New York City’s streets often feels like walking through a living museum, especially when you get to explore its clandestine past. The Secret Speakeasies and History Experience promises an intimate journey into the days of Prohibition, uncovering secret bars, stories of immigration, and iconic landmarks—all in about three hours.

This tour isn’t just about sipping cocktails; it’s about connecting with the city’s rebellious spirit and cultural fabric.

What we love about this experience is how it blends history and fun in a small-group setting. The guides are knowledgeable and passionate, making history come alive with lively stories. Plus, the panoramic skyline views from a rooftop lounge add a layer of visual magic.

One thing to consider is that the tour involves walking, so moderate physical fitness is recommended. This tour suits travelers who enjoy history, lively atmospheres, and a taste of NYC’s underground culture.

Whether you’re a history buff, a cocktail enthusiast, or simply looking for a unique way to see Midtown Manhattan, this experience offers a well-rounded taste of New York’s Prohibition-era charm. It’s especially ideal for those who appreciate small-group intimacy and want to skip the touristy lines—plus, it’s an excellent value at just $36 per person. Let’s explore what makes this tour so engaging and worth your time.

Key Points

Small group size: Intimate experience with a maximum of 15 travelers ensures personalized attention.
Rich historical context: Guides recount stories of Prohibition, immigration, and NYC landmarks.
Quick access: Free and express entry at each venue keeps the mood relaxed and efficient.
Spectacular views: Panoramic cityscape and Empire State Building sightings from a rooftop lounge.
Diverse venues: Visit at least three historic bars, each with its own vibe and history.
Cost-effective: Great value for the mix of education, entertainment, and exclusive access.

A Closer Look at the Itinerary

Walking Through Times Square

The tour kicks off in the heart of Midtown Manhattan, right in Times Square. While this area is famous for neon lights and crowds, the guide highlights its deeper story—how this bustling hub played a role during the Prohibition era. You’ll get a quick snapshot of the neighborhood’s immigrant roots and its transformation into the entertainment capital we know today.

Travelers often comment on how engaging the guide is, with reviews like, “Ariel was terrific! We loved her stories and drink recs, and the speakeasies were such fun!” This opening sets the stage for a mix of sightseeing and storytelling that feels genuine, not scripted.

Rooftop Views of Manhattan

Next, you’ll ascend to a rooftop lounge offering panoramic views of the city skyline, including a close-up of the Empire State Building. The vistas are a highlight, giving you a chance to appreciate NYC’s scale and beauty, especially as the sunset paints the city in golden hues. Many reviewers mention how this elevated perspective makes the experience special, like Dawn who said, “We were able to learn about some New York history while we went to the different Speakeasies.”

The Heart of Broadway and Hell’s Kitchen

The tour then takes you through the Broadway district, famous for its theaters and restaurants. Here, your guide recounts stories of immigration and the neighborhood’s role during Prohibition. You’ll learn how illegal bars thrived, often run by Irish mobs, giving you a sense of the city’s resilience and resourcefulness during tough times.

Historic Bars and Speakeasies

The core of the experience involves visiting at least three historic bars, some of which have ties to the Prohibition era. These venues are handpicked for their authenticity and atmosphere. While the first bar is noted for its secretive vibe—“kind of speakeasy-ish”—the others are known for their vibrant atmosphere and high-end cocktails.

What really sets this part apart is the storytelling. Guides recount the secret codes, hidden entrances, and the exciting underground culture that these bars fostered. You might find that the ambiance varies—from cozy, dimly lit rooms to lively, bustling spots—all adding to the rich tapestry of NYC’s drinking history.

Cocktail Culture and Modern-Day Speakeasies

While alcoholic beverages are not included in the tour price, the venues offer drinks for purchase, often crafted with care and flair. Many reviewers mention that the cocktails are pricey but worth the experience—highlighting the artistry and craftsmanship behind each drink. A participant noted, “The cocktails are definitely an experience, but they’re pricey.” This suggests that you’re paying for quality and ambiance, not just the alcohol.

Why This Tour Works for Travelers

Authentic Experience: Unlike generic bar crawls, this tour emphasizes history and storytelling. It’s ideal for those who want more than just a night out—participants come away with a newfound appreciation for NYC’s underground culture and the events that shaped it.
Knowledgeable Guides: The rave reviews about guides like Ariel, Ryan, Kate, and others show how their enthusiasm and storytelling skills elevate the tour beyond a simple pub crawl. As one reviewer put it, “Arielle was an amazing guide! She brought the history to life.”
Convenient Logistics: The free and express entry at each venue means more time enjoying the drinks and atmosphere rather than waiting in lines. This is especially helpful in busy times or popular venues.
Panoramic Highlights: The rooftop view adds a memorable visual component that many tours lack—ideal for photo-ops and soaking in the cityscape.
Cost and Value: At $36, the tour offers a lot of value—small group intimacy, cultural insights, exclusive access, and a chance to experience some of NYC’s most historic bars without the hassle of planning.

Potential Drawbacks: Some travelers mention that not all venues are equally exciting or “secret.” A review pointed out that two of the bars visited weren’t out-of-the-way or particularly special, leading to the perception that some stops might feel less memorable. Also, alcohol costs are additional, which can add up depending on your drinks choices.

Detailed Breakdown of the Experience

Meeting Point and Initial Impressions

You’ll gather at 825 8th Ave, a convenient midtown location. The group size is capped at 15, ensuring a cozy, friendly environment where everyone can hear stories and ask questions. Many reviews praise the tour guides for their friendliness and knowledge, making the experience feel personal rather than cookie-cutter.

Walking Through Midtown and Times Square

Once assembled, your guide walks you through the historic streets, pointing out landmarks that played roles during Prohibition. It’s a brisk introduction, setting a tone of curiosity and discovery. One guest remarked, “Walter was awesome and we had a great time. Really a great way to spend an evening!”

Captivating Skyline and Rooftop Experience

The ascent to the rooftop lounge is a highlight that transforms the tour from street-level sightseeing to a scenic escape. The views stretch across Manhattan, with the Empire State Building towering nearby. That feeling of being high above the city, surrounded by it’s lights, makes the experience memorable.

Exploring Prohibition-Era Neighbourhoods

The walk through Hell’s Kitchen and Broadway reveals how the immigrant communities and organized crime fueled the speakeasy culture. The guide recounts the stories of Irish mobs and clever concealment, which many find fascinating. According to a guest, “Ryan navigated us around Midtown and provided an excellent narrative of the history of Prohibition.”

Visiting Historic Bars

The core part of the tour involves visiting three bars, each with its own character. Some are modern takes on speakeasies, while others are authentic vintage venues. The first venue is noted for its hidden entrance, creating a genuine speakeasy feel. The other two venues are lively, with some guests noting the drinks are pricey but well-crafted—adding to the overall value. As one reviewer said, “Drinks were great, and there was plenty of time to enjoy them.”

The Drinks and Atmosphere

While the tour price doesn’t include alcohol, you’ll find a variety of cocktails, craft beers, and small bites available at each stop. Many find the drinks worth the extra expense for the experience and quality. It’s a perfect way to taste NYC’s cocktail craftsmanship while soaking in the historic ambiance.

Who Will Love This Experience?

This tour is best for those who enjoy history, lively city vibes, and small-group intimacy. It’s ideal for travelers who want more than just a bar crawl—they seek stories, atmosphere, and a sense of participation in NYC’s underground culture. If you’re curious about the city’s immigrant past, organized crime, or just looking for a memorable night with scenic views, this tour hits the mark.

It’s also suitable for first-time visitors who want an overview of Midtown’s landmarks and hidden corners. The moderate pace and manageable walking make it accessible, but be prepared for some standing and walking during the tour.

The Sum Up

The Secret Speakeasies and History Experience offers an engaging, well-rounded way to explore New York City’s Prohibition-era background. The guides’ passion for storytelling and the mix of historic sites, skyline views, and lively bars make it a standout activity for those interested in culture and cocktails. Priced at just $36, it provides notable value, especially considering the personalized experience and exclusive access.

This tour is particularly suited for travelers who appreciate authentic stories, scenic views, and the thrill of secret spots. Whether you’re a history enthusiast, a nightlife lover, or simply seeking a unique NYC experience, it’s a night well spent.

However, if your primary goal is to visit only certain bars or you’re sensitive to spending on drinks, keep in mind that alcohol is purchased separately and some stops may feel less “hidden” than expected. Still, the overall vibe, stories, and views make this a memorable way to spend an evening in Midtown.

FAQ

Is this tour suitable for people with moderate physical fitness?
Yes, the tour involves walking and standing, so moderate physical fitness is recommended. It’s not overly strenuous but requires comfort with some outdoor walking.

Where does the tour start and end?
The tour begins at 825 8th Ave in Midtown Manhattan and ends in Hell’s Kitchen. The exact locations are conveniently located for easy access.

Are drinks included in the tour?
No, alcoholic beverages are not included. Drinks are available for purchase at each venue, and many guests find them well worth the extra cost.

How many bars will we visit?
You’ll visit at least three historic bars, each with a different atmosphere and history.

Can I cancel if my plans change?
Yes, the tour offers free cancellation up to 24 hours in advance for a full refund. Cancellations less than 24 hours prior are not refunded.

Is this tour good for solo travelers?
Absolutely. Many guests join solo and end up making new friends, thanks to the small group size and friendly guides.

In short, this NYC speakeasy tour offers a compelling combination of history, scenic views, and lively venues—all at a fair price. If you’re in Midtown and eager to peek behind the city’s secretive past, it’s a memorable experience worth considering.