Nashville: Speakeasy Secrets Roaring 20s Cocktail Crawl

If you’re looking to add a splash of glamor and a dash of history to your Nashville trip, this Speakeasy Secrets Roaring 20s Cocktail Crawl might just do the trick. While I haven’t taken this exact tour myself, I’ve reviewed plenty of experience descriptions and guest feedback, and it sounds like a lively, stylish way to explore Nashville’s secret side.

What really catches the eye is how it blends vintage cocktails with captivating stories of bootleggers, daring women, and jazz-age mischief. Plus, it’s hosted by a witty guide in Gatsby-era style, which promises a fun, immersive vibe.

One thing to keep in mind is that drinks are not included in the ticket price—an approach that allows you to pick your favorite cocktails or non-alcoholic drinks at each stop, making it flexible for different budgets and preferences.

This tour suits those who love nightlife, history buffs with a cheeky streak, or anyone celebrating a special occasion—think birthdays, bachelorette parties, or just a stylish night out.

Key Points

• Authentic Vintage Experience: The tour takes you through Nashville’s best hidden-gem bars that evoke the Prohibition era.
• Engaging Storytelling: Your host shares true tales of crime, scandal, and daring characters from the 1920s.
• Flexible Drink Options: You choose your drinks at each bar, paying separately—whether it’s a classic cocktail or sparkling water.
• Relaxed Pace: Less than a mile of walking over two hours, with plenty of time to sit, sip, and socialize.
• Photo-Ready Settings: Many venues are perfect for Gatsby glam photos or just fun party snaps.
• Ideal for Celebrations: Great for birthdays, bachelorettes, or anyone who loves a playful, history-infused night out.

You can check availability for your dates here:

What to Expect from the Nashville Speakeasy Secrets Cocktail Crawl

This experience promises more than just a bar hop. It’s a storytelling adventure, a history lesson, and a celebration of vintage style rolled into one. Starting outside a central Nashville hotel, your guide—a lively, Gatsby-flair-wearing host—sets the tone with quick introductions and a wink. You’ll get a brief overview of Nashville’s hidden nightlife before heading into your first venue.

The First Stop: A Stylish Cocktail Lounge

Your journey begins at an upscale, old-world style lounge that feels like stepping back into the 1920s. This venue is chosen for its authentic look and vibrant atmosphere. Here, you can order your first drink separately—whether it’s a vintage cocktail like a Bee’s Knees or something more modern—and listen to tales of smuggling, scandal, and coast-to-coast headlines involving notorious figures.

Guests often comment on the atmosphere here, noting that the venue’s decor and vibe do a good job of transporting you to the Prohibition era. “The storytelling was fantastic, and the setting was just perfect for a first sip,” one reviewer shared.

Downtown Stroll and Hidden Gems

After the first stop, you’ll stroll through downtown Nashville streets—stories and fun facts pepper the walk. This part of the tour is light and social, with plenty of banter and historical tidbits.

You’ll visit three more venues, each with its own character and charm. These are carefully selected for their Jazz Age aesthetic, craft drinks, and inviting atmospheres. Whether you’re raising a Sidecar or a Gin Rickey, you’ll find yourself in Insta-worthy spots that feel like they’re straight out of a 1920s movie.

The Second and Third Venue Highlights

Guests often mention these venues as the real highlight—hidden, character-filled spots where the history is palpable. True stories from that time—like daring flappers, clever bootleggers, or comical law enforcement encounters—are woven into the experience.

The venues are chosen for their character and craft, so expect a mix of cozy corners and lively bar areas. These spots allow plenty of time to sit, sip, and chat, with the guide usually sharing fun facts along the way. From some reviews: “It’s a great mix of history and fun, with a relaxed pace that never feels rushed.”

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The Grand Finale: A Toast in Style

The tour ends at a swanky final venue, where everyone raises a glass to toast the evening’s adventures. The group tends to be lively, often making new friends and sharing laughs.

The Experience in Detail

• It’s a walking tour, covering less than half a mile total, so comfortable shoes are a must.
• Duration is about 2 hours, making it a perfect evening activity.
• The group size is generally small, creating an intimate vibe.
• The pacing is relaxed, with ample time to sit and enjoy each venue.
• Drinks are pay-as-you-go, giving you flexibility to choose what suits you, whether cocktails, soda, or water.
• Dress in Gatsby glam or flapper style if you want to add to the fun—many guests do, and it makes for great photos.

What the Reviews Say

Guests have praised the value for money, noting that the tour feels like a well-paced, entertaining history lesson with plenty of laughs. One reviewer mentioned: “The guide’s stories kept us hooked, and the entire experience felt like a true Gatsby party.”

Others appreciated the variety of venues, describing them as hidden gems with character. A common theme was how the tour strikes a good balance between storytelling and socializing, and that the optional dress-up adds an extra layer of fun.

Who Will Love This?

This tour is a hit for history lovers, nightlife enthusiasts, and anyone wanting a unique way to see Nashville’s secret bars. It’s especially suited for celebrations and special nights out, but also works well for couples or groups of friends wanting to enjoy a lively, themed experience.

The Practicalities

• Cost & Value: At $54 per person, this isn’t a cheap night out, but considering four venues, storytelling, and the overall atmosphere, most guests find it quite reasonable. Remember, drinks are extra, so budget accordingly.
• Meeting Point & Timing: You’ll meet outside a downtown hotel—usually near the Courtyard by Marriott—dressed in your best Gatsby style or just your comfortable shoes.
• Accessibility & Limitations: The tour is wheelchair accessible and can accommodate most guests, but note that it involves walking less than a mile.
• Weather: Rain or shine—dress sharp, and bring an umbrella if needed.

Final Thoughts

The Nashville Speakeasy Secrets Roaring 20s Cocktail Crawl offers a delightful mix of history, glamour, and fun. It’s a chance to experience Nashville’s hidden nightlife while learning true tales of the Prohibition era. The relaxed pace, engaging storytelling, and beautiful venues make it a memorable night out.

This experience is best for those who enjoy a little history with their cocktails, love dressing up, or just want to explore Nashville’s secret side in style. Whether celebrating a special occasion or simply craving a different way to see the city, it’s a well-rounded option.

While not a traditional bar crawl with included drinks, the pay-as-you-go system gives you flexibility and control over your spending. If you’re a fan of vintage aesthetics, lively storytelling, and a touch of glamour, this tour could be just what you’re looking for.

FAQ

Is the tour suitable for non-drinkers?
Absolutely. Drinks are optional, and you can stick to water or soda. The focus is on the experience, stories, and atmosphere.

How long does the tour last?
It runs for about 2 hours, covering less than half a mile of walking, with plenty of time at each venue to relax and socialize.

Are the venues accessible?
Yes, the tour is wheelchair accessible, but it’s always good to confirm specific needs when booking.

What should I wear?
Dress comfortably for walking, but if you want to join in the fun, Gatsby glam or flapper flair is encouraged and makes for great photos!

Are drinks included in the ticket price?
No, drinks are paid for separately at each venue, allowing you to choose exactly what you want.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund, making it flexible for changing plans.

What if it rains?
The tour goes ahead in any weather—dress sharp and bring an umbrella if needed.

Whether you’re a history buff, a night owl, or just looking to do something unique in Nashville, this cocktail crawl combines fun, history, and style in a way that’s hard to beat. Cheers to a memorable night out!

You can check availability for your dates here: