Exploring Nashville’s nightlife often means country tunes and honky-tonks, but this tour offers a different side—one filled with vintage style, secret doors, and stories of the Prohibition era. The Speakeasy Secrets Roaring 20s Cocktail Crawl is designed for those who want to step back into the Jazz Age, enjoy crafted cocktails, and hear true crime tales from America’s secretive Prohibition days.
What we love about this experience is how it combines history with fun—you’re not just sipping drinks; you’re experiencing an era. The host’s witty storytelling makes the past come alive, and the hidden venues add an exclusive feel. Plus, the flexibility to choose your drinks and the optional Gatsby glam shots make it feel personalized. However, keep in mind that this is a walking tour, so comfortable shoes are a must.
This tour is perfect for history buffs, date night couples, bachelorette parties, or anyone looking for a stylish, spirited way to discover Nashville beyond the usual. If you enjoy stories, cocktails, and a touch of glamour, you’ll find plenty to love here.
- Key Points
- Introduction: A Stylish Step Back in Time
- The Itinerary: A Night of Vintage Style and True Tales
- First Stop: An Elegant Cocktail Lounge with Old-World Charm
- Walking Through Downtown: Quirky Facts and Hidden Stories
- Second and Third Stops: Hidden Gems with Character
- Grand Finale: Toast in Gatsby Glam
- What to Expect: An Authentic, Fun Night Out
- The Cost and Value: Paying for What You Love
- Practical Tips for Participants
- Who Will Love This Tour?
- Final Thoughts: Is It Worth It?
- FAQ
- Final Words
- Our Top Picks in Nashville
- More Tour Reviews in Nashville
- Not for you? Here's more things to do in Nashville we have recnetly reviewed
Key Points
- Authentic 1920s Atmosphere: Visit four carefully selected Prohibition-inspired venues with unique jazz-era decor.
- Engaging Storytelling: Learn true crime and wild tales from the Prohibition days, all delivered with humor and flair.
- Flexible Drink Options: While cocktails are purchased separately, you get to choose what suits your mood—classic, modern, or non-alcoholic.
- Walking Experience: Cover less than half a mile over two hours, with comfortable pacing and plenty of time at each stop.
- Photo Opportunities: Capture stylish moments in Gatsby glam or in the ambiance of secretive speakeasies.
- Inclusive Vibe: Everyone is welcome, whether you’re a cocktail connoisseur or just curious about the era.
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Introduction: A Stylish Step Back in Time
This Roaring 20s cocktail crawl in Nashville promises a lively, immersive experience for anyone intrigued by the jazz age, bootleggers, and speakeasy secrets. While I haven’t taken this particular tour myself, the glowing reviews and detailed descriptions suggest it’s a well-crafted way to combine history, nightlife, and a touch of glamour.
Two standout features immediately catch the eye. First, the chance to sip vintage cocktails in some of Nashville’s most hidden gem bars genuinely intrigues us. These venues, chosen for their jazz-age aesthetic and craft drinks, help set the scene for a night of fun and storytelling. Second, the witty host adds an element of entertainment—delivering tales of smuggling, scandal, and daring bootleggers with humor and flair, making history feel fresh and lively.
One possible drawback is the cost of drinks, which aren’t included in the ticket price. While this gives you the freedom to pick what you want, it does mean budgeting an extra $10-$15 per stop. Also, since it’s a walking tour, those with mobility issues or uncomfortable shoes might find the pace a little brisk, especially if they want to linger at each venue.
This experience suits anyone who loves history with a bit of mischief, enjoys dressed-up fun, or just wants a memorable night out with friends or a partner. It’s a lively way to see a different side of Nashville—one that whispers of the past, not shouts.
You can also read our reviews of more tours and experiences in Nashville.
The Itinerary: A Night of Vintage Style and True Tales
The tour kicks off outside a centrally located downtown hotel, where your dressed-to-impress guide greets you with a wink and a nod to the Gatsby era. This initial meet-and-greet sets a playful tone, and from there, the adventure begins.
First Stop: An Elegant Cocktail Lounge with Old-World Charm
Your journey begins at a stylish bar that oozes vintage flair, reminiscent of a 1920s jazz club. The decor might include dim lighting, leather booths, and art deco accents, transporting you back in time. Here, you might order your first cocktail—perhaps a Bees Knees or a Sidecar—which you purchase separately. The host shares tales of smuggling, scandal, and colorful characters who made headlines coast to coast during Prohibition.
What makes this stop stand out is the authentic atmosphere and the chance to get comfortable before the stories and drinks start flowing. Several guests have mentioned how “the host’s storytelling is engaging and hilarious,” turning what could be a simple bar visit into an interactive history lesson.
Walking Through Downtown: Quirky Facts and Hidden Stories
Between stops, you’ll stroll through Nashville’s lively streets, hearing quirky fun facts and tales of secret speakeasies that once operated in alleyways and basements. This part of the tour adds context and color, giving you a sense of the city’s clandestine past. It’s a chance to stretch your legs and catch your breath before the next venue.
More Great Tours NearbySecond and Third Stops: Hidden Gems with Character
These venues are true surprises—places that have kept their vintage charm and craft cocktail menus intact. One might be a cozy hideaway with vintage posters and jazz recordings softly playing, while another could be a lively spot with a modern twist on classic drinks. Guests have raved about their classic cocktails, noting how well they taste and how well they fit the era’s vibe.
True crime stories and wild tales often accompany these visits, with descriptions of daring bootleggers, daring flappers, and law enforcement shenanigans. One reviewer summed it up: “The stories made the drinks taste even better—they added a layer of mischief and fun to the experience.”
Grand Finale: Toast in Gatsby Glam
The night wraps up at a stylish, perhaps more upscale, venue where everyone gathers for a final toast. It’s a perfect ending to a lively evening—raising glasses with new friends and sharing stories of the night. Guests often comment on how “the entire experience feels like a scene out of a movie,” and many enjoy the last photos taken in full Gatsby attire or in the chic ambiance.
What to Expect: An Authentic, Fun Night Out
This isn’t just a bar crawl—it’s a storytelling journey that blends history, humor, and cocktails. The entire route covers less than a mile, making it manageable for most, with plenty of stops to sit, sip, and socialize.
Pacing is relaxed, which means you’re encouraged to enjoy each venue without feeling rushed. The host’s lively narration, interactive trivia, and photo opportunities make for a fun, memorable night. Plus, everyone is welcome, regardless of their drinking preferences—whether you’re giggling with a soda or savoring a vintage cocktail.
The dress code is flexible—but dressing up in Gatsby glam or flapper style adds to the fun and makes for great photos. Remember, attire is optional but encouraged for that extra touch of authenticity.
The Cost and Value: Paying for What You Love
The $54 ticket price covers the guided tour, storytelling, and access to four distinctive venues, including at least one restricted-access speakeasy. The cost of drinks is separate, allowing you to choose your preferred beverages and stay within your budget.
Many reviews highlight the good value for money: the experience, atmosphere, and stories are worth the price, especially considering the unique venues and lively guide. Guests often mention how the tour feels exclusive without being overly expensive, especially since you can control your drink spending.
The tour is also flexible—you can skip drinks if you prefer, and the guide is friendly about accommodating non-alcoholic options. The tour’s length (two hours) makes it a perfect, manageable nighttime activity—enough to get a real taste of the era without feeling like a marathon.
Practical Tips for Participants
Bring comfortable shoes for walking, and dress in weather-appropriate clothing since the tour is outdoors between stops. Having ID on hand is essential for purchasing alcohol, and cash or card is accepted at venues.
Because the tour operates rain or shine, it’s wise to check the weather forecast and dress accordingly. The tour is suitable for most ages 21 and up, but it’s not recommended for children or those with mobility constraints.
While the tour is lively, it’s designed to be inclusive and fun for everyone—whether you’re a history buff, a cocktail lover, or just looking for a stylish night out.
Who Will Love This Tour?
This experience is ideal for those interested in American history and Prohibition stories, but also for anyone wanting a stylish, social evening. If you enjoy dressing up and taking photos, the optional Gatsby glam adds a lot of photo-friendly fun. It’s great for birthdays, bachelorette parties, or romantic date nights.
It’s also a good pick for nightlife enthusiasts who want to experience Nashville’s hidden side, especially those tired of the usual country scene. The mix of storytelling, craft cocktails, and lively venues makes for a well-rounded, engaging evening.
Final Thoughts: Is It Worth It?
In our view, this Roaring 20s Cocktail Crawl offers a fantastic way to see Nashville through a different lens. The combination of authentic venues, engaging host, and lively stories provides real value for the price. You’re not just drinking; you’re stepping into a storybook of speakeasies, bootleggers, and jazz musicians.
The tour’s relaxed pacing, the flexibility to choose your drinks, and the friendly, knowledgeable guide make it a memorable, enjoyable experience. It’s perfect for those who love history, nightlife, and a bit of glamour—or simply want to add some sparkle to their Nashville visit.
If you’re looking for a fun, sophisticated, and slightly mischievous night out, this tour is a great pick. It’s an easy way to indulge your curiosity, enjoy some excellent cocktails, and walk away with plenty of stories—and perhaps some photos—to share.
FAQ
Are drinks included in the ticket price?
No, drinks are purchased separately at each venue. This allows you to choose your favorites and stay within your budget.
How long does the tour last?
The tour is approximately two hours long, covering less than half a mile of walking with plenty of stops to sit, sip, and socialize.
Do I need to dress up?
Dressing in Gatsby glam or flapper style is optional but encouraged for added fun and great photo opportunities.
Is the tour suitable for non-drinkers?
Yes, non-alcoholic options like soda or water are welcome, and the focus is on the experience and stories, not just cocktails.
Where does the tour meet?
Most days, outside the Courtyard by Marriott at 170 4th Ave N. For the 1:30 PM edition, outside Hotel Indigo / The Countrypolitan at 315 Union St.
Is the tour wheelchair accessible?
Yes, the tour is wheelchair accessible, but check with the provider for any specific needs.
What should I bring?
Comfortable shoes, weather-appropriate clothing, and ID are recommended. Bring cash or card for drinks and tips.
What if it rains?
The tour runs rain or shine, so dress accordingly. Some venues may be indoor or covered, ensuring you stay dry.
Nashville: Speakeasy Secrets Roaring 20s Cocktail Crawl
“It was brilliant! Dean was a great guide and very knowledgeable. What's more, it ended up being just me that had booked onto it… he gave me the o…”
Final Words
If you enjoy stories from the past, craft cocktails, and a sense of exclusivity, this tour delivers a delightful mix. It’s an evening designed to entertain, educate, and transport you to Nashville’s secretive, glamorous days. Whether you’re celebrating a special occasion or just looking to experience the city in style, the Speakeasy Secrets Roaring 20s Cocktail Crawl is a smart, fun choice. With lively storytelling, hidden venues, and good company, it’s a memorable way to get a taste of the Jazz Age—without leaving Music City.
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