Private Speakeasy Adventure A Tipsy Trip through History

Discover NYC's hidden speakeasies on this private, guided tour featuring visits to three historic bars, storytelling, and a lively nightlife experience.

Exploring NYC’s Hidden Nightlife: A Look at the Private Speakeasy Adventure

If you’re curious about the secret corners of New York City’s legendary nightlife, the Private Speakeasy Adventure might just be your next must-try experience. This guided tour offers a fun, informative peek into the city’s Prohibition-era bars and underground venues, all while keeping things safe and social. We haven’t done it ourselves, but based on reviews and the itinerary, it looks like a fantastic way to combine history, good company, and a taste of NYC’s clandestine past.

What really draws us in is how this tour balances storytelling and genuine access. First, you get to visit three iconic speakeasies and historic bars, each with its own unique vibe — from Victorian decor to lively dance clubs. Second, the guide’s storytelling about the Prohibition era promises a richer understanding of the city’s history. An important plus? The tour is well-organized, with express entry and preferred treatment at venues, making it feel like a VIP experience. One potential consideration? You’ll need to be comfortable walking and standing for parts of the tour, and the drinks are not included, so you’ll want to budget accordingly.

This experience seems best suited for those who enjoy nightlife, history buffs, or anyone looking for a safe, social way to uncover some of NYC’s hidden gems. If you’re traveling with friends or love the idea of discovering secret bars, this could be a perfect fit.

Key Points

Private Speakeasy Adventure A Tipsy Trip through History - Key Points

  • Historical insight: Guided storytelling adds depth to the bar visits, making it more than just a pub crawl.
  • Exclusive access: Enjoy express entry and VIP treatment at three historic venues.
  • Variety of venues: From underground speakeasies to Victorian-style bars, the tour offers diverse atmospheres.
  • Flexible scheduling: Choose an early or later evening tour that fits your plans.
  • Safety and company: Guided group means safe navigating NYC’s nightlife with new friends.
  • Price point: $52 per person for three hours, including visits and storytelling, offers good value considering the experience.

A Closer Look at the Tour Itinerary

Private Speakeasy Adventure A Tipsy Trip through History - A Closer Look at the Tour Itinerary

The tour kicks off at 825 8th Avenue in Midtown, a central spot near public transportation, which makes it easy to access. Starting in Times Square, you’ll get to see the iconic lights and the bustling atmosphere, all while soaking in the historic surroundings of what once was the hub of nightlife and entertainment. This area, known as Restaurant Row, sets a lively scene for your night.

Next, you’ll stroll into the Theater District, home to Broadway’s brightest lights and some of the world’s most renowned restaurants. Walking down Restaurant Row here, you’ll get a taste of the city’s vibrant entertainment scene. Your guide will fill you in on the area’s past, particularly its significance during the Prohibition era. It’s a great way to appreciate how this neighborhood evolved from clandestine drinking spots to the world-famous hub it is today.

Your walk takes you into Hell’s Kitchen, a neighborhood with a rough-and-tumble reputation, but also a rich story of immigration and nightlife. Here, you’ll learn about the neighborhood’s darker past and its transformation over the decades. It’s the perfect stop to set the stage for the secret bars ahead.

The highlight comes with visits to three historic venues:

  • The Flute Bar: An original speakeasy, where you’ll get to step into a space that still echoes the secrecy and glamour of Prohibition days. The 45-minute visit includes exclusive access, making it more intimate than typical bars.

  • An iconic dance club: While the specific name isn’t provided, the inclusion of NYC’s most famous dance venue suggests an energetic, lively environment, perfect for those who love to soak in the local nightlife scene.

  • Lillie’s Victorian Establishment: This Victorian-style bar offers a different ambiance—think plush decor, vintage charm, and a cozy atmosphere. Again, with a 45-minute visit included, you’ll have plenty of time to relax, chat, and take in the unique decor.

Throughout the tour, the guide shares fascinating stories about the Prohibition era, making the experience both entertaining and educational. One reviewer mentioned how Ariel was amazing, engaging, and friendly, which highlights the importance of a knowledgeable, personable guide to really enhance the night.

While drinks are not included, that allows you to choose your own beverage—whether cocktails or non-alcoholic options—and manage your budget accordingly. You’ll find the experience is more about the atmosphere, history, and social vibe than just bar hopping.

What We Loved About the Experience

Private Speakeasy Adventure A Tipsy Trip through History - What We Loved About the Experience

The guided storytelling is a standout feature, transforming what could be a simple bar crawl into a mini history lesson. Knowing the stories behind each venue adds a layer of appreciation that makes the visit more meaningful. Plus, with VIP treatment and express entry, you avoid long lines and can enjoy each stop without the usual hassle.

Another highlight is the variety of venues, ranging from underground speakeasies to Victorian decor. This diversity keeps the tour engaging and visually interesting. The fact that the tour is scheduled in the evening offers flexibility and the chance to experience NYC after dark—a time when the city really shows its vibrant personality.

The tour’s small group setting (max 40 travelers) ensures you won’t feel lost in a crowd. Instead, it offers a more personalized experience, and the friendly atmosphere encourages mingling and making new friends. Reviewers have echoed this sentiment, praising the guide’s engaging manner and the friendly group dynamic.

Potential Downsides or Considerations

While most feedback is positive, it’s worth noting that drinks are not included in the price, so you should budget extra if you want cocktails during the stops. Also, participants are advised to bring a government-issued ID or passport to verify their age—since the minimum drinking age is 21, this is something to keep handy.

The tour involves walking and standing, so it’s not ideal if you have mobility issues or prefer a more relaxed experience. Dress code is upscale casual, meaning sportswear or ripped clothing aren’t permitted, so plan accordingly for a smart-casual look.

Lastly, since the tour is limited to a maximum of 40 people, booking in advance is recommended, especially during busy seasons. The experience is designed for adults interested in nightlife and history, so it’s not tailored to families or children.

Final Thoughts: Who Should Consider This Tour?

Private Speakeasy Adventure A Tipsy Trip through History - Final Thoughts: Who Should Consider This Tour?

If you love exploring neighborhoods with a story, enjoy vibrant nightlife scenes, or want to see parts of NYC most visitors miss, this tour hits the right notes. It’s perfect for history buffs, social butterflies, or groups of friends looking for a memorable evening. The storytelling, VIP access, and variety of venues make it stand out as a well-rounded experience.

If you’re after a lively, educational, and safe way to experience New York’s underground bars, this tour offers an engaging, authentic peek into the city’s clandestine past and present.

Ready to Book?

Private Speakeasy Adventure A Tipsy Trip through History



5.0

100% 5-star

“Ariel was amazing. Engaging, fun, friendly. I truly enjoyed the night and the drinks. The people on the tour were friendly.”

— A Tripadvisor Reviewer, Jun 2025

FAQ

Private Speakeasy Adventure A Tipsy Trip through History - FAQ

Is this tour suitable for families or children?
No, the minimum drinking age is 21, and the tour is designed for adult participants interested in nightlife and history. It’s not suitable for children or families.

How long does the tour last?
The tour lasts approximately 3 hours, giving enough time to explore multiple venues, hear stories, and enjoy the atmosphere without feeling rushed.

Are drinks included in the price?
No, drinks are not included. You can purchase alcoholic or non-alcoholic beverages at each venue, so budget accordingly.

Where does the tour start and end?
It begins at 825 8th Ave in Midtown Manhattan and ends in Times Square, making it convenient for public transit and other evening plans.

Do I need a reservation?
Yes, the tour is booked in advance, and you receive a mobile ticket. Booking ahead is recommended to secure your spot.

What should I wear?
The dress code is upscale casual—no sportswear or ripped clothing. Dressing smartly enhances the experience and helps you blend into the stylish venues.

All in all, the Private Speakeasy Adventure offers a thoughtful, fun way to discover NYC’s secret bars, learn about its Prohibition past, and enjoy a lively evening out. Whether you’re a history enthusiast, nightlife lover, or just someone eager to see a different side of the city, this tour has a lot to offer.