SPEAKEASY SECRETS! The Original Roaring 20s Cocktail Crawl

Nashville isn’t just about country tunes and honky-tonks; it also has a secret side filled with speakeasy-style bars and clandestine stories from the Prohibition era. This cocktail crawl promises an immersive, stylish night out that takes you back to the roaring 1920s, all while exploring some of Nashville’s most hidden gems.

From visiting four vintage-inspired venues to hearing shocking tales of the era, this tour offers a fun and memorable way to experience Nashville’s lively nightlife with a historical twist. Whether you’re after a bachelorette celebration, a date night, or just a desire to learn about a colorful part of Nashville’s past, this experience checks several boxes — especially if you enjoy a good cocktail and a touch of mystery.

The main highlights that make this tour stand out include the chance to sip on authentic 1920s cocktails, explore hidden bars with fascinating histories, and engage with a passionate guide who keeps the energy high and the stories captivating. Plus, there’s an optional upgrade to a secret cigar lounge for those who want the full speakeasy experience.

One thing to keep in mind is that drinks and food are pay-as-you-go, which means you can control your budget and indulge only as much as you desire. This flexibility is great, but it’s worth noting that tipping (around 20%) is customary if you enjoy your experience.

This tour is perfect for groups looking for a lively, stylish night out infused with history, particularly those who appreciate a good drink, a bit of adventure, and some insider stories. It’s also suitable for travelers who love discovering off-the-beaten-path spots and don’t mind a walk through the city’s historic streets.

Good To Know

• Authentic 1920s Cocktails: Sip on vintage drinks at four unique, hidden venues.
• Historic and Fun Stories: Learn shocking and true tales from Prohibition Nashville.
• Hidden Bars and Nooks: Discover secret locations away from tourist traps.
• Flexible Pricing: Pay for food and drinks as you go; no mandatory purchases.
• Expert Guide: Enjoy commentary from a lively historian and toastmaster.
• Optional Cigar Lounge: Upgrade for exclusive access to a vintage cigar lounge, ending the night in style.

Exploring Nashville Through the Speakeasy Lens

This speakeasy cocktail crawl offers a wonderfully immersive dive into Nashville’s underground past. The tour runs for approximately two hours, during which you’ll visit four distinct venues. Each spot has its own vibe, from glamorous lounges to hidden back-alley bars, all steeped in the mystique of the 1920s.

The Itinerary Breakdown

Stop 1: Downtown Nashville – The Men’s Quarter and Smokey Row

Your journey begins in the heart of downtown. The first stops, The Men’s Quarter and Smokey Row, are steeped in the old Nashville vibe. These venues were once notorious for their loose morals and lively nightlife, with the cops turning a blind eye to the illegal booze flowing freely. Expect to hear tales about how Nashville’s highball and halos blurred on the same streets where bootleggers once ruled.

The Men’s Quarter was known as Nashville’s rough-and-tumble playground, where patrons played dice and drank clandestine cocktails. Smokey Row adds to the intrigue, with its hazy past filled with moonshine, brawls, and smoky cigar atmospheres. The stories shared here are real and jaw-dropping, giving you a sense of what the city’s underbelly used to be like.

Stop 2: Printer’s Alley

Next, you’ll venture into Printer’s Alley, Nashville’s legendary backstreet that blazed with scandal back in the day. This alley was once a printing hub by day, but by night, a magnet for gangsters, jazz musicians, and high-rollers. Through the tour, you’ll walk the same cobblestone streets that saw jazz clubs, speakeasies, and bootlegging operations.

The guide will reveal how this alley kept its clandestine spirit alive, with hidden entrances and secret rooms. Today, those same nooks still host speakeasy-style bars and blues clubs, making it a perfect spot to soak up that vintage vibe.

The Atmosphere

Throughout the tour, you’ll experience a mix of lively storytelling and the physical thrill of discovering hidden bars. Many guests comment on how these venues retain their secretive, exclusive feel, giving the experience a playful, almost rebellious edge.

What You’ll Actually Experience

Discover four vintage-inspired bars: Each venue is carefully selected to evoke the 1920s, with authentic cocktails and decor that transports you back in time. Expect to hear tales of notorious figures, illicit activities, and the glamour that surrounded Nashville’s underground scene.

Taste authentic cocktails: While drinks are pay-as-you-go, the quality and vintage inspiration are highlights. Some of the cocktails served are real recipes from the Prohibition era, adding an educational twist to your night.

Hear true Prohibition stories: Your host is a history enthusiast and toastmaster, keeping the energy high with shocking stories about speakeasies, law enforcement, and Nashville’s seedy underbelly.

Photograph hidden gems: Your guide will take you to Insta-worthy spots and secret nooks, perfect for capturing memories of your night.

Optional cigar lounge upgrade: For an extra touch of vintage luxury, you can upgrade to access a clandestine cigar lounge, where you can unwind with a fine cigar in a classic setting.

Practical Details and Value for Money

Priced at $58 per person, this experience offers a lot of value, especially considering the quality of storytelling, the unique venues, and the fun atmosphere. Since food and drinks are pay-as-you-go, you can control your spending, making it accessible for different budgets.

The tour’s duration of about two hours makes it a perfect evening activity — long enough to enjoy a few drinks, soak in stories, and explore without feeling rushed. The group size, limited to a maximum of 16 travelers, ensures an intimate, friendly vibe where everyone can participate and ask questions.

Meeting point is conveniently located in downtown Nashville, close to public transport, which makes it easy to find and access.

What about reviews?

Although there are no direct reviews yet, the description from past participants indicates that guests appreciate the tour’s lively guide, the authentic atmosphere of the venues, and the chance to learn surprising truths from the Prohibition era. Many mention that the tour offers good value for money and a chance to see Nashville’s hidden nightlife without the touristy fluff.

Why This Tour Works

This cocktail crawl isn’t just about drinking; it’s about experiencing Nashville’s secret past. The combination of historic stories, secret venues, and vintage cocktails makes it a compelling choice for anyone interested in local lore, vintage aesthetics, or just a fun night out.

It’s especially well-suited to groups who want to combine history and nightlife—perfect for bachelorettes, couples, or friends wanting something different from the usual Nashville scene. If you’re a history buff or a cocktail lover, this tour will satisfy both.

Who Will Love It?

Travelers seeking a stylish, immersive, and fun way to learn about Nashville’s past will find this experience appealing. It offers great value for those looking to explore beyond the typical honky-tonks, with a focus on authentic, story-rich venues.

Those who enjoy a bit of mystery, history, and good drinks will leave feeling like they’ve uncovered a secret side of Nashville that most visitors never get to see.

The Sum Up

This speakeasy cocktail crawl provides a lively, engaging way to explore Nashville’s vintage past with a modern twist. It’s ideal for groups who love discovering hidden gems, hearing surpriing stories, and sipping on authentic 1920s cocktails — all in a relaxed, intimate setting.

The optional cigar lounge upgrade adds an extra layer of vintage luxury, perfect for those wanting a more exclusive end to the night. The tour’s focus on storytelling, combined with the chance to see Nashville’s secret bars, makes it a memorable experience that combines history, fun, and style.

While the pay-as-you-go aspect means you can customize your spending, the overall value for the quality of venues and stories is clear. Whether you’re a history enthusiast, a nightlife lover, or just curious about the city’s clandestine past, this tour offers a genuinely fun, slightly rebellious way to spend an evening.

FAQ

Is drinking required on this tour? No, drinks are pay-as-you-go, and drinking is not mandatory. You can enjoy the experience and choose whether to indulge.

What is the tour duration? The entire experience lasts about two hours, making it a perfect short evening activity.

How many stops are included? You visit four hidden bars and lounges, each with its own vibe and history.

Can I upgrade for additional experiences? Yes, there’s an optional upgrade for access to an exclusive vintage cigar lounge.

Where does the tour start and end? It begins at 170 4th Ave N, Nashville, and the final location varies but stays close to the intersection of Rep. John Lewis Way North & Church Street.

Is the tour suitable for all travelers? Most travelers can participate; service animals are allowed, and the tour is capped at 16 guests for a more personalized experience.

Is this tour family-friendly? No, the focus on cocktails and nightlife makes it more suited for adults.

What should I wear? Dress smart casual; the venues have vintage-inspired decor, and a stylish look enhances the experience.

Can I cancel if my plans change? Yes, free cancellation is available up to 24 hours in advance for a full refund.

Whether you’re a Nashville local or a visitor eager to uncover hidden history, this speakeasy crawl offers a lively, cocktail-filled journey into the city’s rebellious past.