Nashville: Speakeasy Secrets Roaring 20s Cocktail Crawl

If you’re looking for a way to experience Nashville beyond its country music roots, the Speakeasy Secrets Roaring 20s Cocktail Crawl offers a lively, immersive trip back to the Jazz Age. This two-hour adventure isn’t just a bar-hopping tour; it combines history, humor, and style—plus a little sip of the past—into a memorable evening. Whether you’re celebrating a special birthday, planning a girls’ night out, or just love a good story with your cocktail, this tour has a lot to offer.

What makes this experience particularly appealing is its authentic vintage vibe and the chance to sample classic 1920s cocktails in hidden, stylish venues. We also appreciate the witty guiding style, which makes the tour feel more like a private party than a tourist trap. That said, it’s worth noting that drinks are purchased separately, which means you can choose your favorite tipple—whether it’s a gin sidecar or just sparkling water—at each stop. This flexibility allows you to manage your budget and personal preferences.

One possible consideration is that the tour involves walking between venues—covering just under half a mile—so comfortable shoes are recommended. Also, since the tour is all about the 1920s, dressing in Gatsby glam or flapper flair isn’t required but definitely adds to the fun and photo opportunities. This experience suits travelers who enjoy good stories, lively atmospheres, and the chance to feel like they’ve stepped into a vintage movie.

Key Points

• Authentic atmosphere: Experience Nashville’s hidden speakeasies with Jazz Age style and decor.
• Storytelling: Enjoy fascinating tales of bootleggers, daring women, and Prohibition-era madness.
• Flexible drinking: Purchase drinks separately, allowing full control over your choices and budget.
• Interactive fun: Participate in trivia, group photos, and a celebration for the best outfit.
• Walking pace: A relaxed tour covering less than a mile over two hours, with plenty of time to sit, sip, and socialize.
• Suitable for various occasions: Perfect for birthdays, bachelorette parties, date nights, or history buffs.

You can check availability for your dates here:

Exploring the Tour Itinerary in Detail

Starting Point and First Impressions
The tour kicks off outside a centrally located hotel in Downtown Nashville, most often the Courtyard by Marriott or Hotel Indigo, depending on the scheduled session. Here, the guide, dressed in sharp 1920s-inspired attire, greets guests with a wink and a quick overview of what’s to come. It’s a lively start, setting the tone for a night filled with stories, laughs, and a sense of adventure.

Venue 1: Vintage Cocktail Lounge with a Twist
Your first stop is a stylish bar that evokes the glamour of the Roaring Twenties. Expect dark woods, velvet seats, and a cozy ambiance. Here, you’ll be encouraged to order your first cocktail—though drinks are bought separately—and the guide might share tales of smuggling, scandal, and notorious figures from the era. The setting feels intimate and exclusive, perfect for getting into the mood.

Walking Through Downtown Nashville
Between venues, your guide will share quirky facts and secret histories about Nashville’s nightlife, bootlegging, and the big personalities that made the 1920s so memorable. This is a chance to stretch your legs, chat with fellow travelers, and soak in the city’s little-known stories.

Venue 2 & 3: Hidden Gems with Character
Next, you’ll visit two more boutique venues, each chosen for their authentic decor and craft cocktails. These locations are often Insta-worthy, with vintage-inspired signage, jazzy lighting, and an air of mystery. You might raise a Bees Knees or a Sidecar toast here, with the guide narrating tales of daring flappers, clever cops, and bootleggers who knew how to throw a party.

The Final Toast
Your night concludes at a swanky venue where everyone raises a last glass in a celebratory mood. Whether you prefer a classic cocktail or a non-alcoholic option, this last stop feels like the perfect curtain call—an elegant finish to your time-traveling journey.

What to Expect From the Experience

Duration and Pace
This is a two-hour walking experience, typically held in the afternoon or evening. You’ll cover less than a mile, with time to relax and enjoy each venue without feeling rushed. The guide keeps the energy lively but friendly, ensuring everyone has a chance to ask questions or snap photos.

Group Size and Atmosphere
While the tour may vary depending on the day, it typically hosts a small, intimate group, fostering conversation and camaraderie. The guide’s witty, Gatsby-era persona makes storytelling engaging, and the group dynamic adds to the fun.

Cost and Value
The ticket price of $54 per person covers the guided tour, storytelling, access to at least one restricted speakeasy, and themed trivia. Drinks, however, are purchased separately, which many find to be a smart move—giving you the freedom to choose what you want and stay within your budget. When you factor in the exclusive venues, entertaining stories, and the photo opportunities, many consider this a good value for such a unique experience.

Dress and Photo Opportunities
Guests are encouraged to dress in Gatsby glam or flapper flair—though it’s optional, it adds to the fun and makes for memorable photos. The venues are designed for great photo ops, with vintage decor perfect for capturing the spirit of the 1920s.

Authentic Stories and Unique Venues

The tours are praised for their true crime tales and authentic history—not faked or sanitized stories. Guests have remarked on the entertaining narrative style, blending humor with historical facts, which makes learning about Prohibition’s chaos surprisingly fun. For example, one reviewer noted, “The guide’s stories about daring bootleggers and gutsy women made the era come alive.”

The venues themselves often carry a hidden or exclusive feel, with some access to restricted speakeasies, giving you a true taste of the clandestine nightlife during Prohibition. The decor, the ambiance, and the clever history make each stop a mini adventure in itself.

The Value of the Experience

At $54, this tour offers a solid value for an evening of entertainment, history, and socializing. You’re paying for the guide’s storytelling, the ambiance of four carefully selected venues, and the chance to dress up and feel part of a roaring party. Since drinks are pay-as-you-go, you can control how much you spend, whether you want a fancy cocktail or just enjoy the atmosphere with sparkling water.

Reviewers often mention the fun of the interactive trivia and the photo opportunities, which add extra layers of enjoyment. For many, this experience is a highlight of their Nashville trip—an authentic, lively, and memorable way to get a peek into the city’s secret past.

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Who Will Love This Tour?

This experience is ideal for history lovers with a sense of humor, nightlife enthusiasts, and anyone who enjoys dressing up for fun photos. It’s perfect for bachelorette parties, birthdays, or couples seeking a stylish, relaxed evening. Also, if you’re interested in authentic stories of crime, bootlegging, and daring women, the tales shared here will fascinate.

People who appreciate good value—since the tour offers a lively, story-filled experience without a hefty price tag—will find this a worthwhile addition to their Nashville visit. And if you love a themed, immersive event that combines history with social fun, this tour ticks all the boxes.

FAQs

Are drinks included in the ticket price?
No, drinks are not included and are purchased separately at each venue. This gives you freedom to choose what you want and how much to spend.

Is the tour suitable for non-drinkers?
Absolutely. The focus is on the stories, the atmosphere, and the fun. You can enjoy water or any non-alcoholic beverage and still be part of the party.

How much walking is involved?
The tour covers less than half a mile on foot, so comfortable shoes are advised. The pace is relaxed, with plenty of time to sit, sip, and socialize.

What should I wear?
Dressing in Gatsby glam or flapper flair is optional but highly encouraged if you want to add to the fun and take memorable photos.

Can I join if I’m under 21?
No, you must be 21 or older to participate, and valid ID is required.

How long is the tour?
The experience lasts approximately two hours, typically in the afternoon or evening.

Is the tour wheelchair accessible?
Yes, the tour is wheelchair accessible, making it available to a wider range of guests.

Final Thoughts

The Nashville Speakeasy Secrets Roaring 20s Cocktail Crawl offers more than just a night out; it’s a chance to step into a different era without leaving the city. Its blend of authentic stories, vintage decor, and lively guides keeps it engaging and fun. The flexibility to buy your own drinks makes it adaptable to different budgets and preferences, ensuring everyone can enjoy the spirit of the 1920s.

Whether you’re a history buff, a party lover, or someone who just wants to experience Nashville’s hidden side, this tour delivers a memorable mix of storytelling, style, and socializing. It’s a smart choice for a relaxed, entertaining evening that adds a splash of glamour to your visit.

In short, this experience is perfect for those who love a good story, a fine cocktail, and dressing up for a night out. It’s a lively, authentic, and uniquely Nashville way to celebrate the city’s vibrant nightlife and secret past.

You can check availability for your dates here: