NYC: Glitz Glam and Gangsters Drinking Tour

If you’re looking to add a spirited twist to your NYC trip, the Glitz, Glam, and Gangsters Drinking Tour by TellTaleTours offers a fun, engaging way to explore Hell’s Kitchen. This tour promises a lively blend of history, secret bars, and stories of the neighborhood’s transformation from lawless gangland to Broadway hotspot. It’s an experience that feels like catching up with an old friend who knows all the city’s juicy stories.

What we really like about this tour is its affordable price point—just $23 per person for three hours of entertainment—and the focus on storytelling, which makes each stop much more than just a drink venue. Plus, the fact that you get free and express entry at each of the five locations means less waiting and more drinking. That said, a potential downside is that drinks are not included, so you’ll need to budget for your beverages, which can add up depending on what you order.

This tour works well for anyone curious about NYC’s gritty past and thriving nightlife. It’s especially suited for those who enjoy history served with a splash of humor, or travelers wanting a social, relaxed evening that’s both educational and lively. Just keep in mind the dress code (business casual) and the walking involved—this isn’t a leisurely sit-down kind of experience.

Key Points

• Affordable Price: At $23, it offers good value for a 3-hour guided experience.
• Focus on History & Stories: Learn the real stories behind Hell’s Kitchen’s transformation.
• Five Iconic Venues: Visit legendary bars, pubs, and speakeasies with free entry.
• Social & Interactive: Join a small group led by a licensed guide, with chances to win prizes.
• No Drinks Included: Be prepared to purchase your own beverages at each stop.
• Moderate Walking: You’ll walk around 1.5 miles, so comfortable shoes are a must.

You can check availability for your dates here:

What to Expect from the Tour

When you sign up for the NYC: Glitz, Glam, and Gangsters Drinking Tour, you’re signing up for a lively journey through Hell’s Kitchen. The tour lasts around three hours, mostly in the evening, and takes you to five iconic and history-filled venues. Each bar, pub, or speakeasy has its own story to tell, and your guide will be sharing tales of gangsters, Prohibition-era whispers, Irish immigrant roots, and the neighborhood’s evolution into a Broadway-sized playground.

The Venue Stops

Expect to visit legendary bars and secret speakeasies that are part of NYC’s drinking lore. These aren’t just spots for a quick drink—they’re part of the city’s fabric, tied to stories of mobsters like the Westies, Irish immigrants, and the showgirls who danced through its streets. The experience is tailored to give you exclusive, express entry, so you skip lines and spend more time soaking in the atmosphere.

The Stories and Atmosphere

The storytelling is a highlight. You’ll learn about how Hell’s Kitchen’s reputation shifted over the decades, from a rough-and-tumble neighborhood to a vibrant entertainment hub. The license-guided narrative dives into real crime stories, Irish immigrant battles, and the neighborhood’s connections to Broadway. It’s a mix that keeps the mood lively and informative without feeling heavy.

Social Aspect & Prizes

The group tends to be intimate — perfect for a relaxed, conversational vibe. Plus, there are prizes at each stop for contest winners, which adds a bit of playful competition. The guide’s local knowledge keeps the stories engaging, and the small group size ensures everyone can participate.

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The Drinking Experience

While the tour doesn’t include drinks, you’ll have plenty of opportunities to purchase cocktails, beers, or non-alcoholic drinks at each venue. The focus is on the experience, not just drinking for drinking’s sake. Expect to find a variety of options at each stop, and remember that dress code is business casual—think smart, not sloppy.

Detailed Breakdown of the Stops

The five venues are carefully chosen for their historical significance and atmosphere. While specific bars aren’t named in the materials, you can expect to visit legendary spots that have been part of the neighborhood’s lore for generations.

Stop 1: A bar with roots going back to the Prohibition era, likely a speakeasy or a place with a secretive past. You’ll hear about the neighborhood’s lawless roots and may get a glimpse of how bootleggers operated.

Stop 2: A pub or lounge that Irish immigrants helped shape, filled with stories of their battles and contributions. You might hear about the Irish building and fighting for this neighborhood.

Stop 3: A venue that once hosted showgirls and gangsters alike, possibly with historic decor or a vintage feel that transports you back to the roaring twenties.

Stop 4: A modern glamor spot that’s now part of the Broadway scene, showing how the neighborhood has transformed without losing its edge.

Stop 5: The final destination, where the past and present collide, and you can reflect on the neighborhood’s dramatic transformation.

The Practical Side

Duration & Timing: This is a 3-hour tour, usually in the evening, which makes it ideal for unwinding after a day of sightseeing. Keep in mind you’ll need to meet the guide at least 5 minutes early to account for delays, especially during busy times or holidays.

Cost & Value: For just $23, you’re getting a guided walk through history with included express entry and prizes, which is a good deal compared to paying for individual drinks or entrance fees. However, since drinks are not covered, your total cost will depend on what you order.

Group Size & Guide: The tour is designed for a small, intimate group led by a licensed NYC guide who is fluent in English. This makes for a more personalized experience, and the guide’s storytelling adds a lot of value.

Accessibility & Dress Code: It’s not wheelchair accessible, and guests should be dressed in business casual. This isn’t a casual bar crawl in flip-flops—think stylish yet comfortable.

What to Bring: Your ID (a copy is fine), some cash or card for drinks, and a curious mind ready for stories and surprises.

Who Is This Tour Best For?

If you’re fascinated by NYC’s rough-and-tumble past and love discovering city secrets, this tour will suit you well. It’s perfect for those who want an entertaining, informative evening without breaking the bank. It’s also a good pick for travelers who appreciate storytelling, history, and a lively social atmosphere.

However, if you’re looking for a family-friendly or wheelchair-accessible experience, this may not be suitable—it’s geared toward adults comfortable with walking and spending a few hours in bars. The focus on Irish immigrant history, gangsters, and Prohibition means the content is geared more toward mature audiences.

Final Thoughts

This NYC tour balances history, fun, and nightlife in a way that feels authentic and engaging. For just $23, you get to explore some of the city’s most legendary bars, hear stories you won’t find in guidebooks, and enjoy a relaxed, social atmosphere. It’s a great choice if you want to add a bit of storytelling and local flair to your evening plans.

The small group size and expert guide make it personalized, and the focus on historic venues means you’re not just drinking but also learning about the neighborhood’s complex past. It’s best suited for adults who enjoy a good story, a well-made cocktail, and a taste of NYC’s legendary past.

If you’re prepared to walk a mile and a half, spend a bit on your drinks, and love a dose of history with your night out, this tour could be just the ticket for your NYC visit.

FAQ

Is the tour suitable for children?
No, this tour is designed for guests aged 21 and over. Drinks are not included, but you’ll be purchasing your own beverages, so it’s not appropriate for minors.

How much should I budget for drinks?
Drinks are not included, so you’ll want to plan for additional expenses depending on what you order at each venue. Expect to pay for your own drinks.

What’s the dress code?
Guests should wear business casual attire—think neat and tidy, not athletic or casual beachwear.

Can I cancel the tour if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund, offering flexibility if your plans shift.

Is the tour wheelchair accessible?
No, unfortunately, it isn’t wheelchair accessible, so consider this if you or your travel companions need accommodations.

How long does the walk involve?
You’ll walk approximately 1.5 miles during the tour, so comfortable shoes are recommended.

Are drinks included?
No, drinks are not included, but there are plenty of opportunities to purchase at each venue.

Where do we meet?
The meeting point is on 8th Avenue across from Carnegie Diner, near the citi bikes, between 49th and 50th streets.

What language is the tour in?
The guide speaks English. No other languages are specified, so it’s best for English speakers.

If you’re curious about NYC’s gangster past, love a good story, and want to enjoy some of the city’s best bars without the hassle of lines, this tour could be a surprisingly rewarding pick. Just remember to come with your curiosity, some cash for drinks, and a comfortable pair of shoes.

You can check availability for your dates here: