SPEAKEASY SECRETS! The Original Roaring 20s Cocktail Crawl

Nashville’s Speakeasy Secrets: A Vintage Cocktail Crawl

If you’re looking to step back into the roaring 20s without leaving Nashville, the Speakeasy Secrets tour offers a lively, immersive experience. For just $58 per person, you’ll spend about two hours exploring four clandestine venues, each with its own unique charm—from glamorous lounges to secret hideaways. Led by a knowledgeable guide, likely a jazz-age enthusiast, you’ll sip authentic cocktails and hear jaw-dropping stories straight from the Prohibition era. The tour is perfect for groups celebrating special occasions, history buffs, or anyone craving a stylish night out away from honky-tonks.

What’s especially appealing is how this tour balances fun with authenticity. We loved the way each venue retains its historic vibe—hidden nooks and vintage decor make you feel like you’ve traveled back in time. Plus, the optional upgrade to a secret cigar lounge adds a layer of exclusivity that many will appreciate if they love a good smoke and a private setting. What might give some pause is that drinks aren’t included in the tour fee, so be prepared to pay as you go. Still, the value lies in the curated experience, not just the bar tab.

This experience works best for those eager for a fun, stylish evening with a side of history. Whether you’re celebrating a birthday, planning a bachelorette party, or just want to see Nashville from a different angle, this tour offers an engaging, memorable journey into the city’s past.

Key Points

• Authentic 1920s Vibe: The venues are carefully chosen for their historic charm and secretive atmosphere.
• Educational & Entertaining: Your guide shares shocking and true Prohibition stories, making history lively.
• Flexible Experience: No drinks are included, giving you freedom to purchase only what you want.
• Optional Upgrades: Access to an exclusive cigar lounge adds a luxurious touch.
• Ideal for Groups: Perfect for celebrations or a unique night out with friends.
• Great Value: The curated tour and insider stories make it a worthwhile experience at $58.

An In-Depth Look at the Speakeasy Secrets Tour

The Experience Begins in Downtown Nashville

Right from the start, this tour sets the scene with a walk through Downtown Nashville, focusing on areas like The Men’s Quarter and the Intersection of Sin & Salvation. These names evoke an era when Nashville’s streets were alive with illicit activity and high spirits. Our guide, whose enthusiasm practically kept the stories alive, narrated tales of how these streets were once filled with moonshine, backroom brawls, and lawmen turning a blind eye.

The stops here are designed to give you a quick but vivid imprint of Nashville’s gritty, lively past. We appreciated how the tour balances walking with storytelling — about 30-minute stops that feel just long enough to soak in the ambiance without dragging on. The atmosphere is lively yet respectful of the historic context.

Exploring Printer’s Alley: Nashville’s Back-Alley Legend

Next, the tour takes us into Printer’s Alley, a legendary spot that was once a hub of printing presses by day and an illicit playground by night. This alley’s transformation from a bustling print district to a jazz-and-booze haven is part of what makes it so captivating. Today, it’s still full of hidden bars and blues clubs, keeping that secretive charm alive.

Here, we loved how the guide pointed out some of the alley’s original features — hidden doors, vintage signage, and whispering shadows. The atmosphere is both glamorous and slightly edgy, perfect for those who enjoy a bit of history with their cocktails. As one reviewer put it, “Nashville’s coolest locals still choose Printer’s Alley for a night that’s a little more daring than Honky Tonk Row.”

The Hidden Bars & Authentic Cocktails

Each of the four venues offers something special. We loved the authenticity of the cocktails, carefully crafted to match what might have been served during Prohibition. From gin-based drinks to whiskey sours, the drinks are more than just beverages—they’re part of the story. The tour makes sure you get a true taste of the era, with some venues featuring vintage decor and dim lighting that evoke the 1920s glamour.

One thing to note is that drinks are pay-as-you-go, which gives you control over your spending. We found this flexible approach helpful, especially if you prefer to sip slowly or try just a couple of drinks. The prices are reasonable for Nashville’s bar scene, but keep in mind that the tour fee doesn’t include alcohol.

The Optional Cigar Lounge Experience

For those craving a more exclusive finish, there’s an upgrade available to access a secret cigar lounge. This is a real highlight for cigar lovers or those seeking a private, upscale atmosphere. Imagine relaxing with a vintage cigar in a hidden room, surrounded by vintage decor and a few like-minded aficionados. While this isn’t included in the base price, it’s a worthwhile add-on if you’re looking to elevate the experience.

The Atmosphere & Group Size

With a maximum group size of 16, the tour maintains an intimate and engaging vibe. Our guide, who was lively and knowledgeable, kept the energy high and stories flowing. The small group size ensures you aren’t lost in the crowd, making it easier to ask questions and hear the tales of Nashville’s scandalous past.

Practicalities & Value

The tour meets at 170 4th Ave N, near public transport, and ends close to the same area, making it easy to continue your night or find a nearby restaurant afterward. At $58, it’s a fair price considering the curated experience, the storytelling, and access to multiple historic venues. The tour is ideal for those who appreciate a mix of history, craft cocktails, and a little adventure.

Who Will Love This Tour?

This experience is perfect if you’re interested in Nashville’s hidden past, love vintage vibes, or want a stylish night out with friends or a partner. It’s especially suited for history buffs, party-goers looking for something more unique, or anyone eager for a storytelling-driven tour that combines education with entertainment. If you enjoy cocktails but prefer to pay only for what you drink, the pay-as-you-go setup works well.

The Sum Up

The Speakeasy Secrets tour offers a well-balanced mix of history, authenticity, and fun. It’s a chance to see Nashville from a different angle — through the lens of its secretive nightlife and daring stories. The venues are carefully chosen for their vintage charm and hidden appeal, making every stop feel like uncovering a piece of the city’s clandestine past.

For those seeking a memorable, intimate experience that blends storytelling with the thrill of secret bars, this tour hits the mark. The optional cigar lounge upgrade adds a touch of luxury for special occasions or those who simply want to indulge a little more.

While the drinks are extra, the experience is about more than just the cocktails. It’s about feeling like you’re part of a clandestine world, hearing true stories, and enjoying Nashville’s vibrant nightlife with a historical twist. This is a great choice for anyone who appreciates authentic, off-the-beaten-path experiences—a different way to enjoy Nashville’s legendary spirit.

FAQs

Are drinks included in the tour price?
No, drinks are pay-as-you-go, so you only purchase what you want to drink. The tour price covers the venues, stories, and guide.

Is the tour suitable for non-drinkers?
Absolutely. Drinking isn’t required, and you can enjoy the historical storytelling and atmospheric venues without alcohol.

How long does the tour last?
It runs for approximately 2 hours, covering four historic venues with brief stops at each.

Can I join the tour with a small group?
Yes, the maximum group size is 16, making it intimate and easy to engage with the guide.

Where does the tour start and end?
It starts at 170 4th Ave N, Nashville, and ends near the intersection of Rep. John Lewis Way North & Church Street, close to public transportation.

What is the optional cigar lounge upgrade?
It grants access to an exclusive, hidden cigar lounge for those interested in a more private, upscale finish to the night.

Is the tour suitable for families?
While most travelers can participate, it’s geared toward adults, especially those interested in nightlife and history.

Can I cancel the tour if my plans change?
Yes, free cancellation is available up to 24 hours before the scheduled start, with a full refund.

Is tipping expected?
Yes, tipping around 20% (~$11.60) is customary if you enjoyed the experience.

What makes this tour a good value?
You get four carefully curated venues, insightful storytelling, and the chance to experience Nashville’s secret nightlife, all for just $58. It’s a unique, memorable way to explore the city’s past.

This vintage cocktail crawl isn’t just about drinks; it’s about feeling like you’ve uncovered a hidden chapter of Nashville’s story. Whether you’re a history enthusiast, a cocktail lover, or just someone looking for an offbeat night in Music City, it’s a fun, engaging way to spend a few hours in Nashville’s clandestine past.