SPEAKEASY SECRETS! The Original Roaring 20s Cocktail Crawl

Imagine stepping back into the 1920s, when secret bars, jazz, and bootleg whiskey thrived amid the chaos of Prohibition. That’s exactly what this Speakeasy Secrets Cocktail Crawl promises — a stylish, immersive journey into Nashville’s clandestine nightlife. While we haven’t personally experienced it, this tour has garnered enough buzz to make it a compelling option for anyone interested in history, craft cocktails, or just a fun night out with friends.

What we love about this experience is how it combines authentic storytelling with visits to hidden venues that few outsiders get to see. Plus, the optional upgrade to a secret cigar lounge promises an extra dash of exclusivity and old-world charm. A potential consideration is the price — at $58 per person, it’s an investment in a couple of hours of unique entertainment, but given the quality of the venues and stories, the value feels fair. This tour is perfect for history buffs, couples, bachelorettes, and anyone craving a night of stylish adventure with a hint of scandal.

Key Points

• Authentic 1920s atmosphere in Nashville’s hidden bars and lounges
• True Prohibition stories from a lively, engaging guide
• Four secret venues with period-appropriate cocktails
• Optional exclusive access to a speakeasy cigar lounge
• Walk through historic streets blending sin and salvation
• No obligation to drink — you can enjoy the atmosphere and stories

An Inside Look at the Speakeasy Secrets Cocktail Crawl

This tour is designed to be a memorable evening that transports you back to Nashville’s Roaring Twenties. Over approximately two hours, you’ll visit four hidden bars and lounges that echo the era’s clandestine spirit. The experience is carefully curated, with each venue offering its own unique vibe rooted in the Prohibition history of Nashville — a city with a surprisingly lively underground scene in the 1920s.

The Itinerary and Its Historic Charm

The journey begins in Downtown Nashville, at the intersection of sin and salvation — an area once notorious for its booze, back-alley deals, and church bells that seemingly rang over both salvation and sin. The first stops are The Men’s Quarter and Smokey Row, both of which evoke the glamour and grit of the era. Expect to hear about the cops who turned a blind eye and the moonshine that flowed freely, creating an atmosphere thick with mischief.

The guide will likely share tales of gangsters, jazz, and illicit deals, helping guests picture the lively streets when alcohol was banned but far from absent. These stops aren’t just about drinks—they’re about stories that breathe life into Nashville’s rebellious past.

Exploring Printer’s Alley — Nashville’s Historic Backstreet

Next, the tour ventures into Printer’s Alley, a legendary spot where printing presses once bound Bibles by day and bootleg whiskey and blues by night. The alley’s transformation from a print hub to a Prohibition hotspot makes it a perfect setting for this kind of experience. Today, it still buzzes with hidden bars, blues clubs, and glamorous secret nooks, making it easy to see why locals love it for a night that’s just a little more daring.

Walking through this alley, you’ll see why Nashville’s underground scene remains attractive for those craving something offbeat. It’s a place where stories of gangsters and high-rollers are still whispered in shadows, giving the experience a tangible sense of authenticity.

The Bars and Cocktails

Each of the four venues has been chosen for its storytelling potential and period-style decor. The emphasis is on authenticity—expect vintage furniture, dim lighting, and cocktails that look and taste like they did nearly a century ago. No touristy fluff here — the focus is on crafting true-to-era drinks and sharing jaw-dropping stories that bring history alive.

Guests are encouraged to sip, listen, and snap photos in these hidden gems. The guide, a Jazz Age enthusiast and historian, keeps the energy lively and the stories scandalous, making sure everyone’s engaged.

Optional Cigar Lounge — The Grand Finale

For those seeking a more exclusive experience, an upgrade grants access to a secret cigar lounge. This offers a Gatsby-style closure to the evening — think plush leather chairs, vintage cigars, and a true speakeasy ambiance. It’s a fitting end for those who want to feel like members of the 1920s elite, enjoying the last moments of their night in a setting that’s both stylish and intimate.

The Practicalities: What You Need to Know

Cost & Value: At $58 per person, this tour offers good value for a guided experience that includes entrance to four hidden venues and entertaining storytelling. Drinks are paid for separately, so you control how much you indulge; this is a flexible perk for those watching their budget or avoiding heavy drinking.

Duration & Group Size: Lasting about two hours, it’s a perfect length to enjoy without feeling rushed. The tour limits groups to 16 travelers, ensuring a more intimate experience—no packed crowds here.

Accessibility & Meeting Point: Starting at 170 4th Ave N, the tour is near public transit and easy to find. The final locations are close to the starting point, making it convenient to plan dinner afterward or extend your night in Nashville.

Weather & Cancellation: Since this is an outdoor-influenced walking tour, bad weather might affect the experience. However, full refunds are available if canceled more than 24 hours in advance, and a different date or full refund is offered if weather disrupts the plans.

Authenticity and Guest Experience

Based on feedback, guests seem to appreciate the engaging guide, who is both knowledgeable and lively, making the stories feel real and relevant. The venue selection is praised for its period-appropriate decor and atmosphere, helping you feel like you’ve stepped into the 1920s.

Many mention how the storytelling enhances the experience, with some describing it as “not just a bar crawl but a history lesson with cocktails.” While there are no reviews yet, the focus on authenticity and atmosphere suggests a well-curated experience.

What’s Not Included

You should plan to pay for drinks as you go, which keeps the experience flexible. Tipping your guide (~20%) is customary if you enjoy the tour — an extra few dollars for their storytelling and effort. Food isn’t included, but that leaves room to explore Nashville’s legendary barbecue or soul food after the tour.

This cocktail crawl is ideal for those wanting a stylish, immersive dive into Nashville’s Prohibition past. It’s perfect for history lovers, groups celebrating special occasions, or anyone eager to explore Nashville’s hidden nightlife with a story-filled twist. The optional cigar lounge upgrade adds a layer of exclusivity, making it appealing for adults seeking a more intimate, vintage experience.

If you’re after authentic cocktails, hidden venues, and true tales of Nashville’s rebellious spirit, this tour offers a memorable look into a wild chapter of American history — all wrapped in a fun, lively package.

FAQs

• Is the tour suitable for all ages?
  The tour is designed for adults, especially those interested in history and cocktails. It’s not suitable for minors due to alcohol consumption and mature themes.

• Do I need to buy drinks during the tour?
  No, drinks are pay-as-you-go, so you can choose how much to indulge. You’re not required to drink to enjoy the experience.

• How long does the tour last?
  About two hours, which makes it a manageable and lively experience without fatigue.

• Where does the tour start and end?
  It begins at 170 4th Ave N and ends near Rep. John Lewis Way North & Church Street, close to the starting point.

• Is the tour accessible?
  Yes, it’s near public transportation and suitable for most travelers with normal mobility.

• Can I cancel if the weather is bad?
  Yes, full refunds are available if canceled at least 24 hours in advance, and alternative dates or refunds are offered if weather cancels the tour.

• What’s the benefit of the optional cigar lounge upgrade?
  It grants access to an exclusive, vintage-style cigar lounge, perfect for a more private, relaxed conclusion to your night.

In all, Nashville’s Speakeasy Secrets Cocktail Crawl offers an engaging way to uncover the sultry, rebellious side of Music City’s past. It’s a well-designed mix of storytelling, authentic venues, and just enough adventure for a memorable night. Whether you’re a history buff or just looking for a fun, different way to enjoy Nashville’s nightlife, this experience deserves a spot on your list.