Nashville: Speakeasy Secrets Roaring 20s Cocktail Crawl

Nashville’s Speakeasy Secrets Roaring 20s Cocktail Crawl offers a lively glimpse into the Jazz Age, all for $54 per person. This 2-hour tour takes place in Downtown Nashville, where you visit four distinct venues inspired by the Prohibition era, all with a Gatsby flair. Led by a witty guide with a Roaring ’20s style, the experience combines history, humor, and stylish drinks for a memorable night out. The tour is perfect for birthday crews, bachelorettes, date nights, or anyone eager to explore Nashville’s hidden nightlife with a dash of vintage glamour.

One notable feature is that drinks are purchased separately, allowing guests to choose their favorites—from vintage cocktails like a Sidecar or Bee’s Knees to non-alcoholic options. This flexible approach helps each visitor enjoy exactly what they want at their own pace. The tour’s focus on authentic stories of bootleggers, daring women, and Prohibition chaos makes it as much a history lesson as a party. The only potential consideration is the walking distance—less than a mile—but comfortable shoes are recommended.

Key Points

• Price and Duration: $54 per person for 2 hours exploring Nashville’s best hidden bars.
• Authentic Prohibition Vibe: Four Prohibition-inspired venues with Jazz Age aesthetics.
• Engaging Storytelling: True stories of bootlegging, scandals, and bold women are shared throughout.
• Flexible Drinks Options: Guests purchase their own cocktails or drinks, choosing from vintage favorites or non-alcoholic drinks.
• Glamorous Atmosphere: Optional Gatsby glam attire enhances the experience, with photo opportunities in stylish settings.
• Accessible and Flexible: Meeting outside the Downtown hotel with wheelchair access; cancelations available up to 24 hours in advance.

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Starting Point and Meeting Details in Downtown Nashville

The tour begins outside a centrally located hotel, typically at the Courtyard by Marriott on 4th Ave N, or at Hotel Indigo for the Suns Up, Bottoms Up edition. The guide dressed in Gatsby-style attire greets visitors with a wink, setting a lively tone. Guests should look for someone in Roaring ’20s flair, making the meeting spot easy to find. Since the tour involves walking less than half a mile, comfortable shoes and weather-appropriate clothes are advised. The group size is flexible, but a minimum of four guests is needed to operate the tour.

Inside the First Stop: A Vintage Cocktail Lounge

The tour kicks off at a stylish cocktail lounge that exudes old-world charm, with an ambiance reminiscent of the 1920s. Visitors are encouraged to order their first drink (sold separately) and settle into the vintage vibe. The guide shares stories of smuggling scandals and notorious figures from the era, setting an engaging tone. This initial stop helps guests relax into the prohibition-era mood and prepare for the next stops.

Exploring Downtown Streets Between Venues

After the first venue, the group strolls along downtown Nashville streets, where the guide offers quirky facts and secret histories. These brief walks between stops provide a chance to absorb the lively atmosphere while hearing stories about cops, flappers, and bootleggers. The pace is social and relaxed, allowing plenty of time for photos and mingling. This walk-through highlights Nashville’s hidden nightlife and secrets that echo the Jazz Age.

Discovering the Hidden Gems: Venues with Character

The tour visits three additional venues, each chosen for their authentic 1920s aesthetic and craft drinks. These hidden bars are known for their unique character and craftsmanship. Guests might sip a Bees Knees, raise a Sidecar toast, or enjoy a modern twist on a classic. Each venue features inviting atmospheres that transport visitors back in time, with swanky decor and private nooks perfect for photo ops. The guide shares true crime tales and fun facts about Nashville’s shadowy past.

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The Grand Finale: Toast in a Swanky Venue

The tour culminates in a luxurious, sophisticated venue where everyone raises a final Gatsby-style toast. This celebratory moment allows participants to capture memorable photos and enjoy the spirited stories shared throughout the night. The final stop emphasizes friendship, fun, and vintage glamor, making it an ideal ending to a lively evening.

The Drinking Experience: Flexibility and Fun

Since drinks are purchased separately, visitors can indulge in vintage cocktails, non-alcoholic drinks, or sparkling water—whatever suits their mood. This system ensures that each guest enjoys exactly what they prefer without being tied to pre-paid packages. The focus remains on storytelling, atmosphere, and socializing, with cocktail recommendations provided at each venue. Photo opportunities abound, especially at the stylish venues where vintage Gatsby glam is encouraged.

Style and Dress Code: Gatsby Glam Optional but Recommended

While costumes are not required, guests are encouraged to come dressed in Gatsby glam or flapper flair. Dressing up adds to the photo fun and immerses everyone further into the Jazz Age theme. This optional dress code enhances the visual appeal and makes for great photos. The tour embraces fun and fancy dress, but comfort remains key, especially for walking.

Accessibility and Practical Tips

The tour is wheelchair accessible and operates rain or shine. Guests should bring comfortable shoes, weather-appropriate clothing, and ID (must be 21+). The walking distance is short, about half a mile, making this experience suitable for most physically capable travelers. Since the venues may vary slightly depending on the day, flexibility is built into the schedule.

Who Will Love This Tour?

This Roaring 20s Cocktail Crawl appeals strongly to history buffs, cocktail lovers, and nightlife enthusiasts. It’s a perfect activity for bachelorette parties, birthdays, or stylish dates, especially for those interested in vintage fashion or Gatsby glamour. The storytelling aspect makes it engaging even for those unfamiliar with the era, and fun trivia adds an interactive element. The cost is reasonable, considering the high-quality venues and unique stories shared along the way.

Final Thoughts on the Nashville Speakeasy Secrets Cocktail Crawl

This tour offers a unique blend of history, style, and social fun in Nashville’s hidden nightlife. The expert guide, authentic venues, and flexible drink options make it a value-rich experience. While walking is involved, the relaxed pace and plenty of sitting make it comfortable for most participants. The Gatsby glam dress code adds a playful touch, and the true crime stories keep the experience engaging.

Perfect for those wanting a fun, stylish night out filled with cocktails and stories. This experience is especially suited for those who love vintage aesthetics or want to explore Nashville’s less obvious side. It’s a lighthearted, lively way to enjoy the city’s nightlife with a nostalgic twist.

Frequently Asked Questions

Is there an age restriction for this tour?
Yes, guests must be 21+ to participate, and ID is required.

Are drinks included in the ticket price?
No, drinks are purchased separately at each venue.

How long does the tour last?
The tour lasts approximately 2 hours.

Where does the tour start?
It begins outside a Downtown Nashville hotel, typically the Courtyard by Marriott or Hotel Indigo, depending on the session.

Is the tour accessible for wheelchair users?
Yes, the tour is wheelchair accessible.

What should I wear?
Comfortable shoes are recommended, and dress in Gatsby glam or flapper style is optional but encouraged for photos.

Can I cancel if my plans change?
Yes, full refunds are available if canceled up to 24 hours in advance.

What is the pace of the tour?
It involves less than half a mile of walking, with plenty of time to sit, sip, and enjoy at each venue.

Are snacks or food included?
No, food or snacks are not included but are available for purchase separately if desired.

Will the venues vary?
Yes, venues may differ slightly depending on the day and group size, but all follow the Prohibition-inspired theme.

What is the best way to prepare?
Bring cash or card for drinks, dress in vintage style if you like, and wear comfortable shoes for walking.

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