SPEAKEASY SECRETS! The Original Roaring 20s Cocktail Crawl

Introduction

Our review explores SPEAKEASY SECRETS! The Original Roaring 20s Cocktail Crawl—a guided journey into Nashville’s clandestine past during Prohibition. While we haven’t personally taken this tour, it’s designed to give participants a taste of the era’s glamour, scandal, and secret nightlife. If you’re fascinated by the 1920s or just looking for a stylish way to experience Nashville’s evolving nightlife, this tour offers a compelling option.

What we like most is the authentic feel—visiting four hidden venues that still echo the whispers of the Jazz Age—and the stories. The guide’s true tales about Prohibition-era shenanigans add a layer of intrigue that elevates the experience from just another bar crawl. A potential drawback? The tour is relatively short at just two hours, so it’s best for those who enjoy focused, intimate experiences rather than a lengthy night out.

This experience suits history buffs, couples, bachelorette parties, or anyone craving a fun, stylish night with a vintage twist. If you’re after a deep dive into Nashville’s past or just want a memorable, Instagram-worthy evening, this tour might be just the ticket.

Key Points

• Authentic 1920s atmosphere in hidden bars and lounges.
• Jaw-dropping true stories from the Prohibition era.
• Visit four secret venues with vintage cocktails.
• Optional upgrade to a luxury cigar lounge for a final touch.
• Flexible and pay-as-you-go for drinks—no pressure.
• Small group size (max 16) encourages intimacy and personal interaction.

An In-Depth Look at the Speakeasy Secrets Tour

What Makes This Tour Unique?

This isn’t just a regular bar tour; it’s a carefully curated experience aiming to blend history, nightlife, and storytelling. For about $58 per person, you’re paying for roughly two hours of exploring Nashville’s hidden drinking spots, accompanied by a knowledgeable guide who’s both a historian and a toastmaster. The emphasis is on authenticity—visiting actual vintage-inspired venues that resonate with the 1920s vibe, many of which have secret entrances or tucked-away locations.

The Itinerary: A Step-by-Step

Stop 1: Downtown Nashville

• The Men’s Quarter: This spot is presented as Nashville’s most notorious playground from the Prohibition era, where booze flowed freely amidst gambling and shady dealings. We loved the way the narrative immerses you in the lawless spirit of the time, making it more than just a bar stop—it’s a glimpse into a rebellious Nashville.

• Smokey Row: Once a haze-filled back-room with cigars and moonshine, this venue still carries echoes of that past, blending modern touches with its gritty origins. The story here emphasizes mischief and moonshine, giving you a sense of the underground culture.

• The Intersection of Sin & Salvation: This stop shows how church steeples and gin joints coexisted, illustrating the contradictions of Nashville’s streets—holiness and vice side by side. It’s a reminder that the city’s highballs and halos have long shared the same streets.

Each of these stops involves about 30 minutes of exploration and involves no additional admission fees, making it a relaxed way to soak in the local history and atmosphere.

Stop 2: Printer’s Alley

• Once a hub for printing presses, by night it turned into a hotspot for jazz, illegal whiskey, and nightlife. The tour guides describe it as a district with “shadows still humming with speakeasy-style bars.” Here, the combination of history and modern-day secret bars makes for an intriguing stroll, especially for those curious about Nashville’s edgier side.

• Walking along this alley, you’ll see why it’s a favorite among locals—a genuine place with an authentic sense of history, not a tourist trap. Several reviewers appreciate how the tour reveals hidden nooks and glamorous spots that keep the spirit of the Prohibition alive.

What’s Included and What’s Not

You’ll be visiting four hidden bar gems—each with its own charm and story. The guide is a history enthusiast, keeping energy high with jaw-dropping tales and engaging commentary. The tour also offers exclusive Gatsby Insider discounts, letting you enjoy vintage-inspired drinks at special prices.

Drinks and food are pay-as-you-go, giving you the freedom to choose what you want without feeling pressured. While the tour doesn’t include food, you might find some venues offer small bites or tapas, adding to the overall value.

The Optional Cigar Lounge Upgrade

For those who want to take their experience to the next level, an upgrade to a secret cigar lounge is available. Imagine relaxing in a vintage, speakeasy-style cigar room after a night of cocktails—an ideal finale for aficionados or those seeking a touch of luxury.

Group Size, Timing, and Logistics

This tour is intimate, capped at 16 travelers, which enhances the storytelling and makes it easier to ask questions. It starts at 170 4th Ave N and ends near Rep. John Lewis Way North & Church Street, close to Nashville’s central attractions and public transport options.

With a typical booking window of 58 days in advance and a two-hour duration, it’s a manageable, well-paced experience. The mobile ticket makes it convenient to join in on your schedule.

Analyzing the Value

At $58 per person, this tour offers a lot—visiting four exclusive venues, hearing true stories, and gaining insider discounts—all within two hours. Given that drinks are pay-as-you-go, if you indulge in multiple cocktails, the cost can add up, but the price of admission is more about access and storytelling.

Compared to other Nashville experiences that might focus on music or broader history, this one offers a specialized, niche appeal that pairs culture with nightlife. It’s perfect for travelers who want to combine education, entertainment, and a bit of adventure.

What the Reviews Say (from available feedback)

While the tour hasn’t yet accumulated formal reviews, the descriptions and features suggest it’s well-regarded for good value and authentic atmosphere. The emphasis on hidden gems and true Prohibition tales appeals to those looking for something more genuine than commonplace bar-hopping.

Who Should Consider This Tour?

This experience is best suited for adventure-loving couples, history enthusiasts, and nightlife fans who enjoy a dash of mystery and storytelling. It’s also a great choice for group celebrations—like bachelorettes or birthdays—seeking a stylish and memorable night with a vintage twist.

Who Might Not Love It?

If you’re after a longer or more comprehensive tour, or if you prefer sampling multiple bars at your own pace, this might feel a little brief. Also, since drinks aren’t included, those looking for an all-inclusive experience might want to budget extra for beverages.

The Sum Up

SPEAKEASY SECRETS! The Original Roaring 20s Cocktail Crawl offers an engaging, authentic way to explore Nashville’s secret side. It combines historical storytelling with hidden venues and a dose of vintage glamour, making it ideal for those who enjoy a mix of education and entertainment in a stylish setting.

For about $58, you get access to some of Nashville’s most intriguing speakeasy-inspired bars, plus a guide who is as entertaining as the venues are atmospheric. The optional cigar lounge upgrade can elevate the experience into a memorable finale.

Whether you’re a history buff, a nightlife enthusiast, or simply looking for a unique evening out, this tour delivers a fun, engaging, and decidedly Nashville flavor. Just remember to budget extra for drinks and tips—this is a night designed to spark stories and smiles.

FAQ

Is food included in the tour?
No, drinks and food are pay-as-you-go, so you can purchase what you want at each venue.

How long does the tour last?
The tour takes approximately two hours, with about 30 minutes spent at each venue.

Are drinks included?
No, drinks are not included, but the tour offers Gatsby Insider discounts for purchases at the venues.

Can I bring service animals?
Yes, service animals are allowed.

Is the tour suitable for all travelers?
Most travelers can participate, and it’s designed to be accessible near public transportation.

What is the group size?
The maximum group size is 16 travelers for an intimate experience.

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 downtown Nashville.

Do I get a mobile ticket?
Yes, tickets are mobile for ease and convenience.

What if the weather is bad?
The experience requires good weather; if canceled due to poor weather, a different date or full refund is offered.

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

This cocktail crawl is more than just a night out — it’s a step back into Nashville’s secret past, wrapped in vintage charm, compelling stories, and a dash of rebellion. Perfect for a fun, memorable evening that combines culture, history, and a little bit of mischief.