Nashville: Speakeasy Secrets Roaring 20s Cocktail Crawl

If you’re looking for a way to experience Nashville beyond its well-trodden honky-tonks and country roots, the Speakeasy Secrets Roaring 20s Cocktail Crawl offers a clever, fun, and immersive adventure into the city’s secret side. This two-hour walking tour takes you through some of Nashville’s most charming, hidden-gem venues that evoke the jazz age and Prohibition-era mystique. Whether you’re into vintage cocktails, history, or just a good party, this tour has a lot to offer.

Two things we particularly love about this experience are the authentic atmosphere in carefully chosen venues and the engaging storytelling that makes history lively and fun. The guide’s witty, Gatsby-inspired style keeps things light and entertaining, turning a simple cocktail crawl into a memorable social event. A possible drawback might be that drinks are purchased separately, which could add up if you’re thirsty or want to try multiple cocktails. Still, this approach lets you pick exactly what suits your mood and budget.

This tour suits a variety of travelers—perfect for birthdays, bachelorette groups, couples on a date, or anyone seeking a playful, stylish taste of Nashville’s hidden nightlife. If you enjoy vintage flair, stories with a twist, and a lively, interactive atmosphere, you’ll find this tour both entertaining and rewarding.

Key Points

• Authentic 1920s vibe: Carefully selected venues recreate the glamour and secretive charm of the Prohibition era.
• Interactive storytelling: True crime, wild tales, and vintage slang keep the history engaging.
• Flexibility with drinks: Purchasing drinks separately allows you to choose your favorites and stay within your budget.
• Great for special occasions: Ideal for birthdays, bachelorettes, or a fun date night.
• Inclusive experience: Non-drinkers can still enjoy the social and historical components.
• A walking adventure: Less than a mile over two hours, with plenty of time to sit, sip, and soak in the atmosphere.

You can check availability for your dates here:

An In-Depth Look at the Experience

Starting Point and First Impressions

The tour begins outside a centrally located hotel in Downtown Nashville—most groups meet outside the Courtyard by Marriott at 170 4th Ave N. The host greets guests in sharp, Gatsby-inspired attire and with a wink, instantly setting a playful tone. You might get a quick sip of something before setting off—a small, welcoming gesture that hints at the relaxed, social vibe ahead.

The Venues: Hidden Gems with Character

Throughout the tour, you’ll visit four vintage-inspired venues, each with its own personality and aesthetic. One of the main highlights is that at least one of these venues is a restricted-access speakeasy, adding an element of exclusivity and adventure. These venues are handpicked for their authentic jazz-age decor, craft cocktails, and inviting atmospheres.

The description mentions a stylish cocktail lounge with an old-world feel where you’ll hear about infamous bootleggers and the wild side of the 1920s. The storytelling here is lively—one reviewer appreciated the “tales of smuggling, scandal, and coast-to-coast headlines” that make each stop more than just a drink spot.

Next stops might include hidden bars with eye-catching vintage decor, perfect for snapping some photos—think Gatsby glam or flapper flair. Here, you’ll sample classics like a Bees Knees or toast with a Sidecar, all while hearing stories of daring flappers, gutsy women, and clever bootleggers.

The Atmosphere and Pacing

The entire experience is designed to be relaxed and social. The walking is minimal—less than half a mile over two hours—giving plenty of time to sit and chat at each venue. You’ll share laughs, swap stories, and enjoy the ambiance without feeling rushed. The guide keeps things lively, using humor and vintage slang to bring the era to life.

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The Final Toast and Celebration

The tour wraps up at a swanky, elegant venue where everyone raises a glass together. It’s a fitting end to a lively journey through Nashville’s underground scene. The last round is less about drinking and more about celebrating the shared experience—an ideal way to conclude a memorable night.

Drinks and Additional Costs

Be aware that drinks are purchased separately at each venue. This approach is smart as it lets you choose what you want—whether a vintage cocktail, a modern twist, or sparkling water. The cost can add up if you’re tempted to indulge at every stop, but it also means you have control over your spending and drink choices.

Why This Tour Adds Value

The combination of guided storytelling, exclusive venues, and the chance to dress up makes this tour more than just a bar crawl. It’s an interactive journey into Nashville’s lively past, with a modern-day twist. For those who appreciate history with a sense of humor and a stylish setting, it offers a genuinely fun way to spend an evening.

What Past Guests Say

Multiple reviews praise the blend of humor, storytelling, and authentic decor. One guest described it as “a traveling soirée, a history adventure, and a Gatsby-inspired toast to mischief and glam,” which captures the essence well. Others appreciated the flexibility—”drinks are optional, and you get to enjoy exactly what you’re in the mood for.” The inclusive vibe means that even non-drinkers can participate fully in the fun and stories.

Practical Details

• Price: $54 per person for the two-hour experience, excluding drinks.
• Duration: 2 hours, walking less than a mile.
• Meeting Point: Outside a downtown hotel—most often the Courtyard by Marriott.
• Accessibility: Wheelchair accessible.
• Dress Code: Casual, but dressy or in Gatsby glam for fun.
• Age Requirement: 21+ with valid ID.
• Reservations: Can be made with flexible payment options—reserve now, pay later.
• Cancellation: Full refund available if canceled 24 hours in advance.

Final Thoughts

The Nashville Speakeasy Secrets Roaring 20s Cocktail Crawl offers an engaging blend of history, style, and social fun. It’s a chance to step into the glamour of the Jazz Age while discovering some of Nashville’s best kept secrets. The tour provides a relaxed pace, authentic venues, and entertaining storytelling that makes it a worthwhile experience for those looking for a stylish night out.

For travelers who love vintage aesthetics, storytelling, and a touch of mischief, this tour will hit the right notes. It’s particularly suited for groups celebrating a special occasion, history buffs with a sense of humor, or anyone curious about Nashville’s secret nightlife past. If you want to experience Nashville’s lively, hidden side in a lively and stylish way, this tour deserves a spot on your list.

Is this tour suitable for non-drinkers?
Yes, drinks are optional and pay-as-you-go, so non-drinkers can simply enjoy the stories, atmosphere, and social aspect without purchasing alcohol.

How long does the tour last?
The experience lasts about 2 hours, covering less than half a mile of walking, with plenty of time to sit, sip, and enjoy each venue.

Are the venues accessible for wheelchair users?
Yes, the tour is wheelchair accessible, making it inclusive for a wider range of travelers.

What should I wear?
Casual attire works fine, but dressing in Gatsby glam or flapper style is encouraged for fun photos and to really get into the spirit.

Is this tour suitable for children?
No, the tour is only for guests aged 21 and over, as alcohol is involved.

What is included in the price?
The ticket covers the guide, storytelling, visits to four venues, and access to at least one restricted speakeasy. Drinks are not included but can be purchased separately.

Where do we meet?
Most groups meet outside the Courtyard by Marriott at 170 4th Ave N. The meeting point might vary slightly for specific tour editions.

Can I cancel if my plans change?
Yes, full refunds are available if you cancel at least 24 hours before the tour.

What if it rains?
The tour goes rain or shine. Be sure to dress appropriately for the weather, as walking outside is involved.

What’s the best way to book?
Reservations can be made with “reserve now, pay later” options, giving you flexibility in planning your trip.

Is it a large group?
The group size depends on demand, but the experience is designed to be engaging and intimate enough for lively group interaction.

This tour offers a lively, authentic look into Nashville’s secretive, glamorous past—perfect for those who want to add a dash of history and style to their visit. Whether you’re a history buff, a cocktail lover, or just in search of a unique night out, the Speakeasy Secrets Roaring 20s Cocktail Crawl provides an entertaining, memorable experience.

You can check availability for your dates here: More Great Tours Nearby