SPEAKEASY SECRETS! The Original Roaring 20s Cocktail Crawl

Nashville is famous for its music, but if you’re craving a different kind of nightlife adventure, the SPEAKEASY SECRETS! The Original Roaring 20s Cocktail Crawl might be just what you need. This tour promises an immersive journey into the clandestine world of the 1920s, complete with visits to hidden bars, stories of prohibition-era scandal, and some seriously authentic cocktails. It’s a great pick for those who like their nights a little edgier or who want to combine history with a fun, stylish night out.

What really appeals to us about this experience is its focus on authenticity — from visiting four speakeasy-inspired venues to hearing true tales from the era, it’s not just about drinking but about feeling like you’ve stepped back in time. Plus, the optional upgrade to a secret cigar lounge adds a touch of luxury that’s perfect for a memorable finale. On the flip side, since it’s only two hours long, it’s a quick snapshot rather than an extended dive into the scene, which might leave some wanting more.

If you’re into history, cool hidden spots, and a lively, intimate group setting, this tour could be just right. It’s especially suited for couples looking for a romantic or fun date night, groups of friends, or anyone wanting a more stylish alternative to Nashville’s typical honky-tonk scene.

Key Points

• Authentic 1920s Experience: The tour focuses on genuine speakeasy bars with vintage style.
• Storytelling: Your guide shares true, jaw-dropping tales from the Prohibition era.
• Hidden Venues: Visit four secret bars and lounges, many with Insta-worthy décor.
• Flexible Drinking: Pay-as-you-go for drinks, so you only buy what you want.
• Optional Luxury: An upgrade option gives access to an exclusive cigar lounge.
• Ideal for a Night Out: Perfect for those wanting a stylish, fun experience without a heavy timetable.

What to Expect from the Cocktail Crawl Experience

This two-hour adventure packs in a lot, starting from the moment you meet your guide at downtown Nashville. You’ll be stepping into a world where behind every unassuming door hides a story, a secret cocktail, or a jazz tune that takes you back to the roaring twenties. The tour is designed to keep things lively and engaging, balancing historical tales with good old-fashioned fun.

The Itinerary Breakdown

Stop 1: Downtown Nashville Streets

Your journey begins on the lively streets of downtown Nashville, where the tour touches on the area’s history of illicit activity during Prohibition. You’ll visit The Men’s Quarter, a spot once notorious for its lively, unregulated drinking, and Smokey Row, which used to be a haze of cigars and moonshine. These stops are more about setting the scene—imagine the wild, rebellious spirit of Nashville’s past.

Narratives here are full of scandal and wit. For example, stories of cops turning a blind eye, gangsters, and the mingling of saloons with church steeples. These tales help you understand what made Nashville’s alcohol scene both dangerous and irresistible during the 1920s.

Stop 2: Printer’s Alley

Next, you’ll move into Printer’s Alley, a legendary back street that by night, transformed from a printing hub into a hotspot for jazz clubs, bootleg whiskey, and swaggering gangsters. It’s the perfect setting for a bit of playful mischief, and it still buzzes with that same spirit today.

Here, you’ll feel the thrill of being behind the scenes—narrow alleys, clandestine bars, and stories of jazz legends and lawless nights. It’s a place where the glamour and grit of the past are still very much alive.

Visiting the Hidden Bars

Each of the four venues is considered a gem, often with a vintage or speakeasy vibe that feels like stepping into a different era. These aren’t your average tourist spots, but rather intimate spaces with authentic cocktails and stories. The tour emphasizes the history behind each bar, so you’re not just drinking, but learning and connecting with Nashville’s secret past.

The Cocktails & Atmosphere

While drinks are pay-as-you-go, you’ll find that each bar offers authentic 1920s cocktails—think gin fizzes and whiskey smashes—crafted with care. The atmosphere is relaxed but lively, with a focus on storytelling, music, and good company. If you’re a fan of jazz or vintage décor, you’ll appreciate the effort that goes into the design and ambiance.

The Optional Cigar Lounge Upgrade

For those wanting a more decadent finish, the optional upgrade grants access to an exclusive cigar lounge. It’s a quieter, more refined space where you can unwind with a fine cigar (or two) and reflect on the night’s stories. It’s a small add-on that elevates the experience, perfect if you want to indulge in some of Nashville’s luxury side.

Walking, Sights, and Scenery

This experience is primarily a walking tour through Nashville’s historic streets and alleyways. It’s a laid-back pace, with plenty of opportunities to snap photos in hidden nooks and glamourous spots alike. The tour is designed to be intimate, with a maximum of 16 travelers, so you’ll have room to ask questions and soak in the stories.

While most of the tour stays on foot, remember that the venues are close enough that you won’t be walking for miles. The focus is on the atmosphere, the stories, and the drinks—though you can choose to skip buying alcohol if you prefer.

Price & Value

At $58 per person, the tour offers a solid value considering it combines historical storytelling, visits to four exclusive bars, and a chance to enjoy real vintage cocktails. The price is quite reasonable, especially since drinks are pay-as-you-go, so you only buy what you want. Plus, the tour includes discounts at some venues, which enhances the experience.

The main value lies in the experience of feeling like a part of history—something you can’t get from just walking into a bar on your own. For the price, you’re getting a curated, fun, and visually interesting way to explore Nashville’s past.

What Others Say

While there are no official reviews included in the data, the description suggests it’s a popular choice, booked an average of 58 days in advance. The fact that it’s suitable for groups seeking a stylish, memorable night makes it attractive.

Practical Details & Tips

• Meeting point: 170 4th Ave N, Nashville. Arrive a few minutes early to meet your guide.
• Duration: About 2 hours, making it easy to fit into a broader night out.
• Group size: Limited to 16 people, so expect a cozy, personal experience.
• Weather: The tour relies on good weather; if it’s canceled due to rain, a different date or refund is offered.
• Age & Accessibility: Most travelers can participate, and service animals are allowed.
• Tips: Gratuities are customary—recommend around 20% if you enjoyed yourself.

Who Is This Tour Best For?

This experience shines brightest for those interested in history, vintage style, or hidden Nashville gems. If you love tales of old speakeasies, jazz, or Prohibition-era scandals, you’ll find it intriguing. It also works well for groups of friends, couples, or even a unique bachelor/bachelorette night. It’s not specifically tailored for families or kids, but it’s accessible for most adult travelers.

Final Thoughts

The Speakeasy Secrets Cocktail Crawl offers a lively, engaging way to spend an evening in Nashville. You get to explore the city’s secret past, enjoy authentic cocktails, and absorb stories that most visitors miss. The tour’s emphasis on storytelling and its selection of intimate, vintage-inspired venues make it a genuinely memorable experience. The optional cigar lounge upgrade adds a touch of class for those wanting a more upscale end to the night.

If you’re after a fun, stylish, and immersive night out that combines history with good drinks and great company, this crawl is worth considering. It’s a perfect choice for travelers who appreciate authentic, well-curated experiences that go beyond the usual Nashville scenes.

FAQ

Is drinking required during the tour?
No, drinking is not required. You pay as you go for drinks, so you only buy what you want.

How long does the tour last?
The tour lasts approximately 2 hours, making it a quick yet packed experience.

What’s included in the price?
The price covers visits to four hidden bars, storytelling by your guide, and discounts at vintage venues. Drinks and food are pay-as-you-go.

Can I join if I don’t drink alcohol?
Yes, you can participate without purchasing drinks. The focus is on the experience and stories, not just drinking.

What’s the optional upgrade?
It’s access to a private, exclusive cigar lounge—great for winding down or enjoying a more relaxed vibe.

Is the tour suitable for children or families?
It’s mainly designed for adults and most travelers, so it’s not particularly family-oriented.

Where do I meet the guide?
At 170 4th Ave N, Nashville. Arrive a few minutes early to get settled.

Is the tour accessible?
Most travelers can participate, and service animals are allowed.

What if it rains?
The tour relies on good weather. If canceled due to rain, you’ll be offered a different date or a full refund.

How far in advance should I book?
Booking about 58 days in advance is typical, so plan ahead, especially in high season.

If you’re looking for a stylish, story-filled night in Nashville with a vintage twist, this Cocktail Crawl could be just what you need. It’s a chance to see the city’s secret side, taste some great drinks, and learn stories that bring the past to life.