Nashville: Speakeasy Secrets Roaring 20s Cocktail Crawl

Nashville: Speakeasy Secrets Roaring 20s Cocktail Crawl offers a lively journey into the jazz-age spirit right in downtown Nashville. For just $54 per person, you’ll spend around two hours exploring four specially selected venues, each with its unique character and vintage vibe. Led by a witty, Gatsby-inspired host, this tour promises stories of bootleggers, daring women, and wild Prohibition antics, all while sipping classic cocktails or mocktails of your choosing.

What we really loved about this experience is how flexible it is — you get to select your drinks (from vintage cocktails to sparkling waters), and there’s plenty of time to enjoy each stop without feeling rushed. Secondly, the tour’s storytelling approach makes history come alive, blending true crime tales and slang of the era with the glamor of Gatsby-era style.

A potential consideration? The tour covers less than half a mile on foot, so pack comfortable shoes and be prepared for a leisurely walk, especially if rain is in the forecast. It’s best suited for those who enjoy history, nightlife, or dressing up in period costumes. If you’re celebrating a birthday, bachelorette party, or looking for a fun date night, this is a memorable way to experience Nashville’s secret side.

Key Points

• Authentic Experience: A fun mix of history, comedy, and nightlife, with lively storytelling from a charismatic guide.
• Flexible Drinking: Guests choose their own drinks, making it easy to stay within your budget or preferences.
• Hidden Venues: Access to four prohibition-inspired bars, including at least one restricted-access speakeasy.
• Glamorous Vibe: Dress in Gatsby or flapper attire for added fun and memorable photos.
• Short & Social: Two-hour walking tour with plenty of time to chat, laugh, and sip.
• Ideal for Celebrations: Perfect for birthdays, bachelorette parties, stylish dates, or anyone curious about Nashville’s secret nightlife.

You can check availability for your dates here:

An In-Depth Look at the Nashville Speakeasy Secrets Cocktail Crawl

What is the Experience Really Like?

This tour is much more than just a bar crawl. It’s a lively blend of history, humor, and high spirits delivered through the lens of the 1920s. You start outside a centrally located downtown hotel, typically the Courtyard by Marriott, where your guide — dressed in sharp, period-appropriate attire — greets you with a wink. From that moment, you’re transported into the jazz age.

Your guide, whose storytelling is described as witty and engaging, sets the tone with brief historical context, funny anecdotes, and tales of the era’s scandalous characters. As you walk from venue to venue, you’ll learn about the wild world of bootleggers, daring women, and crooked cops, all while soaking in the aesthetic of each hidden gem.

The Venues and Their Unique Charm

The tour visits four distinct venues, each selected for their authentic 1920s flair and character. The first stop is a stylish cocktail lounge, where the atmosphere feels like stepping into a vintage film. Here, you’ll order your first drink — a vintage cocktail or non-alcoholic option, as drinks are paid for separately — and listen to tales of smuggling and scandal.

Two other venues follow, both boasting incredible decor and craft drinks. You might find yourself raising a Bees Knees or a Sidecar, perfect for Instagram moments and authentic sipping. Each venue’s vibe varies but always centers around that cocktail and jazz era theme.

The final stop is a swanky, upscale venue where a grand toast marks the end of your adventure. The guide will encourage you to snap photos, share laughs, and toast to the roaring twenties.

The Food, Drinks, and Pricing

Instead of including drinks in the ticket price, the tour adopts a smart approach — you order what you want, when you want, and pay separately. This allows you to customize your experience, whether you prefer a fancy vintage cocktail or a sparkling water. This flexibility means you won’t feel pressured into buying drinks you don’t want, making it good value for money.

While no food is included, the focus remains on the vintage cocktails and the stories. Plus, if you’re not drinking alcohol, you’re still very much part of the fun — the spirit of the event is about celebration, storytelling, and camaraderie.

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How Comfortable Is It?

The entire experience involves walking less than half a mile over two hours, with plenty of stops to sit, sip, and chat. The pace is social, unhurried, and designed for maximum enjoyment. The tour is wheelchair accessible, which is a nice touch for inclusivity.

Who Would Enjoy This?

This experience appeals most to history buffs, nightlife lovers, and groups celebrating special occasions like birthdays or bachelorette parties. It’s also great for stylish couples or friends who like dressing up in Gatsby or flapper outfits and taking fun photos. The tour’s relaxed yet lively vibe makes it suitable for those seeking a lighthearted, memorable night out in Nashville.

A Closer Look at the Itinerary

Meeting Point & First Impressions

The tour begins outside a well-located downtown hotel, usually the Courtyard by Marriott. You’ll spot the guide by their distinctive 1920s flair, ready with a wink and a smile. The initial meet-and-greet offers a quick overview of what’s to come — a good way to settle in and get excited.

Venue 1: A Stylish Cocktail Lounge

Here, the mood is set with vintage decor, perhaps with dim lighting, leather chairs, and jazz softly playing in the background. This first stop is where you’ll order your initial drink, and the guide weaves stories of 1920s smuggling, scandals, and daring dames. One reviewer commented, “We loved the way our guide made history so lively and funny, not just dry facts.”

Venue 2 & 3: Hidden Gems

The next two venues are carefully chosen for their authentic atmosphere and craft cocktails. You might raise a Sidecar in a cozy, intimate bar or enjoy a Bee’s Knees in a spot with art deco decor. The tour’s emphasis on storytelling means you’ll often hear about true crime tales, daring flappers, and police antics, all adding flavor to the experience.

A guest from a review summed it up: “It’s like stepping into a different world — glamorous, mischievous, and full of stories you won’t hear anywhere else.”

Final Venue & Toast

The last stop usually feels like a club or lounge with a luxe feel, where everyone raises a glass to conclude the night. The guide encourages photos, and many guests say their favorite part was this grand finale, “a perfect end with good drinks, big laughs, and some great photos.”

The Value Proposition

At $54, this tour offers excellent value considering it includes access to four venues, engaging storytelling, and a chance to dress up and embrace a different era. The pay-as-you-go drink system allows you flexibility — you can indulge more or less depending on your budget and mood.

The experience’s focus on authentic stories and ambiance makes it stand out from typical bar crawls. It’s not about chasing drinks but about savoring the moment, the history, and the camaraderie. Plus, with optional costume suggestions, you can really lean into the Gatsby theme for memorable photos.

Who Should Book This?

This tour is ideal for history fans who love tales of crime and scandal, nightlife enthusiasts eager for a glamor-filled evening, and groups celebrating special occasions. It’s also perfect if you enjoy dressing up and taking photos, making it a fun, social, and slightly glamorous way to experience Nashville after dark. If you’re looking for an immersive, authentic, and entertaining night of vintage cocktails and stories, this is a solid choice.

FAQs

• Is the tour suitable for non-drinkers? Yes, drinks are optional. You can enjoy water or soda, and still be part of the fun and storytelling.
• How long does the tour last? It’s approximately two hours, covering less than half a mile on foot.
• Are the venues accessible? Yes, the tour is wheelchair accessible.
• Do I need to dress up? It’s optional, but many guests enjoy Gatsby or flapper outfits for photos.
• What is included in the ticket price? The ticket covers a guide, storytelling, access to four venues, and fun group activities. Drinks are paid separately.
• Can I cancel? Yes, you can cancel up to 24 hours in advance for a full refund.
• Where does the tour start? Outside a centrally located downtown hotel, typically the Courtyard by Marriott.
• What is the minimum group size? At least four guests are needed for the tour to operate.
• Is this tour suitable for children? No, it’s 21+ due to alcohol consumption.
• Can I bring large bags or strollers? No, large bags, strollers, or pets (except assistance animals) are not allowed.

In Closing

The Nashville Speakeasy Secrets Roaring 20s Cocktail Crawl offers a balanced mix of history, fun, and vintage glamor. It’s a chance to step back into an era of jazz, gin, and rebellion without leaving downtown Nashville. Whether you’re celebrating, seeking a unique night out, or simply a lover of stories and cocktails, this tour delivers a memorable experience. It’s especially suited for those who appreciate a relaxed pace, engaging tales, and a bit of Gatsby-style flair in their evenings. Dress up, sip your favorite drink, and enjoy Nashville’s best-kept secret — a night of mischief, music, and marvelous stories.

You can check availability for your dates here: