The Speakeasy Adventure: A Tipsy Trip Through History

Discover NYC’s hidden speakeasies with this fun and informative 3-hour tour. Enjoy VIP access, storytelling, and historic bars in Midtown Manhattan.

Exploring New York City’s Hidden Drinking Spots with The Speakeasy Adventure

If you’re curious about NYC’s secretive past and want to experience its vibrant nightlife from a different angle, this Speakeasy Adventure offers a relaxed yet insightful way to do just that. While I haven’t personally taken this tour, the glowing reviews and detailed itinerary suggest it’s a solid choice for those interested in history, good stories, and a bit of urban adventure.

What really appeals to us are the privileged access to some of the city’s iconic bars and the engaging storytelling that makes history come alive. Plus, the tour’s capped size of 20 people helps keep things intimate and comfortable. On the flip side, a potential consideration is that drinks aren’t included—you’ll need to budget for at least a couple of beverages—and some might find the focus on socializing a bit light on historical detail. All in all, if you’re looking for an easygoing evening with a focus on fun and local secrets, this tour hits the mark.

It’s best suited for those who enjoy a good mix of history, social experience, and a taste of New York’s legendary nightlife. Whether you’re a first-timer or a seasoned NYC visitor, it’s a relaxing way to explore Midtown while learning a little about the city’s Prohibition-era antics.

Key Points

The Speakeasy Adventure: A Tipsy Trip Through History - Key Points

  • Accessible and Convenient: Starts in Midtown with close proximity to public transportation.
  • Exclusive Experience: Enjoy express entry and VIP treatment at each bar.
  • Knowledgeable Guides: Guides are licensed, friendly, and enthusiastic storytellers.
  • Limited Group Size: Keeps the tour intimate, allowing for interaction and comfort.
  • History & Modern Mix: Combines tales of immigration, politics, and the Prohibition with visits to historic bars.
  • Cost-Effective: At $36 per person, it offers a good value considering VIP access and engaging storytelling.

An In-Depth Look at The Speakeasy Adventure

Why Choose This Tour?

This tour offers a nice balance between historical context and fun. For just $36 a person, you get a three-hour walk through Midtown Manhattan’s lively streets with a focus on its hidden drinking spots. The experience isn’t just about having drinks (though those are available for purchase), but about soaking up the stories that make NYC’s nightlife so unique.

Many reviews highlight the guides’ knowledge and energy, which really makes the difference. For instance, one reviewer said, “Ariel was fun, knowledgeable & energetic,” making the experience both educational and lively. Others mention how guides like Kate or Sarah add a personal touch, making the tour more than just a walk from bar to bar.

What’s Included?

You get priority entry and VIP treatment at three historic NYC bars, along with a licensed, local guide who brings stories to life. The tour also offers a chance to learn about the immigration and political stories tied to the neighborhood’s past, making it more insightful than just a pub crawl.

What to Expect at Each Stop?

First Stop:
The tour kicks off in Restaurant Row, an area famous for its eateries and an interesting mix of old New York charm. You’ll stroll past the lights and energy of Times Square, offering a great backdrop for some photos and first impressions of Midtown.

Second Stop:
This is where the tour really shines—visiting three iconic bars, each with its own story and character. The Blue Room, for example, has Broadway-related items, making it feel exclusive and special. You’re expected to purchase your drinks, but the experience is about the ambiance and stories. Many reviews mention the surprise of seeing Broadway memorabilia and how it adds a layer of exclusivity.

Third Stop:
Here, your guide recounts tales from the Prohibition era and the waves of immigrants that shaped the neighborhood. These stories are woven seamlessly into the bar visits, giving you context on why these places are more than just spots to drink—they’re pieces of history.

What Makes the Guide Stand Out?

From the reviews, guides like Ariel, Kate, and Sarah are praised for their enthusiasm and knowledge. One reviewer said, “Jenna’s got that ‘Best Guide in the City’ badge,” emphasizing how guides can really enhance the tour. Their storytelling adds depth, making history memorable without feeling like a lecture.

The Social Aspect

With a group capped at 20 people, this tour fosters a small-group vibe perfect for mingling and asking questions. Several reviews highlight how fun and easy it is to interact with guides and fellow travelers. For many, this relaxed social setting makes the experience more enjoyable than a typical bar crawl.

The Practical Details

The tour lasts around 3 hours, starting near 8th Avenue and ending in Times Square. It’s designed for those with moderate physical fitness, as it involves walking and standing at each bar. Dress upscale casual—think neat but comfortable, avoiding sportswear or ripped clothing. Since drinks aren’t included, budget for a few beverages, which typically cost around $20 at each bar, as noted in some reviews.

Price and Value Analysis

At $36, this tour is a pretty good deal. When you consider VIP entry, storytelling, and a friendly guide, it offers a lot for the price. You’re paying mainly for the experience rather than the drinks, but the stories and access add significant value.

What Could Be Better?

Some travelers mention that the history portion could be a bit more in-depth. One review pointed out that the guide spoke quickly and assumed some familiarity with Prohibition, which might leave total novices wanting more background. Plus, drinks aren’t included, so if you’re a heavy drinker, you’ll need to budget accordingly.

Who Will Love This Tour?

The Speakeasy Adventure: A Tipsy Trip Through History - Who Will Love This Tour?

This experience is perfect for those who appreciate history, lively storytelling, and local secrets. It’s ideal for solo travelers, couples, or small groups wanting an easygoing night out. If you’re curious about the stories behind NYC’s legendary speakeasies and want VIP access without hefty prices, this tour fits the bill.

It’s not the best choice if you’re after an in-depth historical lecture or a full-fledged pub crawl with all-inclusive drinks. But if you like a relaxed, friendly atmosphere with a knowledgeable guide, you’ll enjoy this outing.

Final Thoughts

The Speakeasy Adventure: A Tipsy Trip Through History - Final Thoughts

All in all, the Speakeasy Adventure offers an engaging, affordable way to see a different side of Midtown Manhattan. The mix of history, exclusive access, and lively guides makes it a memorable experience. Even if you’re not a heavy drinker, the stories and ambiance at each bar give you a true taste of NYC’s secret past.

It’s best suited for those who want a casual, social experience with a dash of history thrown in. Whether you’re new to the city or a seasoned local, you’ll appreciate the insider feel and the chance to explore some of the city’s most iconic historic bars.

Ready to Book?

The Speakeasy Adventure: A Tipsy Trip Through History



5.0

(129)

87% 5-star

“Loved it! Great tour! Fun introduction to 3 Speakeasies! Ariel was very energetic & had so much knowledge about the Prohibition & speakeasies!”

— David N, Feb 2025

FAQ

The Speakeasy Adventure: A Tipsy Trip Through History - FAQ

Are drinks included in the tour?
No, drinks are available for purchase at each venue. Expect to spend around $20 per drink, based on reviews.

How long does the tour last?
The experience runs for approximately 3 hours, giving you plenty of time to enjoy each stop and chat with your guide.

What’s the meeting point?
It starts at 825 8th Ave, near public transportation, making it easy to access.

Is the tour suitable for all physical levels?
It’s designed for travelers with moderate physical fitness, as you’ll be walking and standing for parts of the tour.

What is the dress code?
Upscale casual is recommended. No sportswear or ripped clothing is permitted.

Can I cancel if I change my mind?
Yes, you can cancel up to 24 hours in advance for a full refund. Cancellations within 24 hours are not refunded.

Is this tour good for families or children?
The minimum drinking age is 21, so it’s best suited for adult travelers. It’s more of a social experience than a family-friendly activity.

Does the group size matter?
Yes, the tour caps at 20 people, ensuring a more intimate and personalized experience.

If you’re looking for a relaxed, story-driven way to explore NYC’s hidden speakeasies, this tour offers a fun blend of history and nightlife at a very reasonable price. Just remember to budget for drinks and come ready for an engaging evening with some of the city’s most iconic bars.