Nashville: Speakeasy Secrets Roaring 20s Cocktail Crawl

Taking a step back into the jazz-filled, gin-soaked days of the 1920s, the Speakeasy Secrets Roaring 20s Cocktail Crawl in Nashville promises an evening of vintage drinks, lively stories, and endless Gatsby glamour. This tour isn’t just about sipping cocktails—it’s a playful journey into the secret, sometimes scandalous, life of the Prohibition era in Music City. Whether you’re celebrating a birthday, planning a bachelorette bash, or just love a good story with your drink, this experience offers a mixture of fun, history, and style.

What makes this crawl particularly appealing are three standout features: the chance to visit hidden gem bars with authentic 1920s decor, engaging storytelling from a witty host, and the flexibility to choose your own drinks. Plus, it offers a lively social atmosphere that feels more like a glamorous party than a typical guided tour. The only potential downside? The tour is just two hours long, so those looking for a deep dive into history might find it a bit light. Still, it’s perfect for anyone who craves a taste of Nashville’s secret side, combined with good laughs and great photos.

This tour is best suited for cocktail enthusiasts, history lovers, and anyone wanting a stylish night out with friends, a partner, or even solo. If dressed in Gatsby glam or flapper-style, you’ll blend right into the scene, making it a memorable and photo-worthy outing.

Good To Know

• Authentic Speakeasy Atmosphere: Hidden bars with jazz-age decor and secret doors.
• Engaging Storytelling: True tales of bootleggers, daring women, and Prohibition chaos.
• Flexible Drink Options: Pay for cocktails separately, allowing personal choice and budget control.
• Social & Fun: Group activities, trivia, and a celebratory final toast.
• Short & Sweet: 2-hour walking tour covering four unique venues.
• All-Inclusive Experience: No food included, but plenty of room for your own snacks and drinks.

You can check if your dates are available here:

Discovering Nashville’s Roaring 20s Spirit

This tour offers more than just a walk around town—it’s a lively, interactive experience that combines history, humor, and high spirits. Starting outside a central Nashville hotel, you’re greeted by a host dressed in vintage flair, setting the tone for an evening of mischief and glamor. The guided storytelling is lively, filled with true crime and scandalous anecdotes that keep everyone entertained and eager for the next stop.

The Itinerary: What You’ll Actually Do

Your journey begins outside a Downtown Nashville hotel—most likely the Courtyard by Marriott or Hotel Indigo—where your host, with a quick wink and a witty intro, kicks off the evening. The first venue is a stylish cocktail lounge with an old-world appeal, where you get your first taste of vintage cocktails (ordering separately). Here, the stories of smuggling, scandal, and notorious figures come alive, with your guide sharing colorful tales that set the mood.

As you stroll through Nashville’s lively streets, you’ll visit a total of four venues, each chosen for their distinctive Jazz Age vibe. The venues vary from secret speakeasy-style bars to craft cocktail joints, all with character and a touch of glamour. Expect to sip classics like Bees Knees or raise a toast with a Sidecar in Instagram-worthy settings. The emphasis is on fun and authentic ambiance, with each stop providing a chance to snap photos, share laughs, and learn about the wild side of the 1920s.

The Final Toast

The tour culminates at a swanky, glamorous spot where everyone raises a glass to the roaring past and newfound friends. The last venue often features a celebration element, with the best-dressed guest awarded (just for fun). Since drinks are paid separately, you’re free to choose your favorite vintage cocktail or just enjoy sparkling water if you prefer.

The Walking & Pacing

The total walk is less than half a mile, making it accessible for most guests. The pace is relaxed, with plenty of time at each bar to sit, sip, and soak in the environment. The overall experience feels like a social gathering—there’s no rushing, and the lively storytelling keeps the energy high. If you’re not into alcohol, don’t worry—you’re still very much part of the fun, with options to enjoy non-alcoholic drinks.

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What’s Included & What’s Not

The ticket price of $54 covers the guide, storytelling, access to four venues, and a chance to participate in trivia and themed photo sessions. Drinks, snacks, and additional purchases are paid for separately, giving you control over how much you spend and what you drink. This pay-as-you-go system is smart, allowing everyone to indulge according to preference and budget.

The tour also features access to at least one restricted-access speakeasy, adding an element of exclusivity and adventure. Plus, the guide, often named with a flair, makes the experience lively, engaging, and full of personality.

The Experience from a Reviewer’s Perspective

One aspect that stood out from multiple reviews is how well the tour balances entertainment with education. The guide’s storytelling is lively, with enthusiasts sharing true tales of bootleggers, daring women, and sometimes outright absurd moments from the Prohibition era. A guest noted, “The stories made the drinks taste even better,” highlighting how the narrative adds flavor to the evening.

Guests also appreciate the flexibility of drink choices, with many mentioning how they enjoyed a variety of cocktails, from classic gin fizzes to modern twists. The opportunity to take photos in glamorous surroundings makes for lasting memories, especially when dressed up in Gatsby or flapper attire—something many visitors find fun and photo-worthy.

The social aspect is another high point: group trivia, mingling, and the final toast create a lively, inclusive atmosphere. Reviewers mention that the relaxed pacing and generous sitting time at each bar prevent the experience from feeling rushed. Plus, the experience is suitable for wide age groups, with some noting it’s best for those 21 and over, but accessible to any who enjoy a good story and a stylish night out.

Venue Selection & Atmosphere

Each venue is carefully picked for its authentic or vintage vibe. Some guests specifically mentioned a “hidden gem” bar with an old-world feel, while others enjoyed the modern yet themed cocktails in picturesque settings. The variety ensures every stop feels special, with an emphasis on craftsmanship and ambiance.

Tips & Practicalities

Guests recommend wearing Gatsby glam or flapper-style costumes if you want to fully embrace the theme, though it’s optional. Comfortable shoes are essential for walking between venues. The tour runs rain or shine, so dressing weather-appropriate is always wise.

Since drinks are paid for separately, bringing cash or a card is necessary. The two-hour duration makes it manageable for most, but those with mobility concerns should note the walk is under a mile in total.

Who Should Sign Up

This experience is ideal for history buffs with a sense of humor, nightlife lovers, and anyone eager to dress up and step into the 1920s for a couple of hours. It’s especially fun for birthday parties, bachelorette groups, or couples seeking a classy, social night out. Non-drinkers are welcome too, enjoying the environment and stories without alcohol.

In summary, this tour offers a well-balanced look at Nashville’s hidden speakeasy scene with plenty of entertainment, stunning photo ops, and engaging storytelling—all in a lively group setting. It’s a memorable way to experience Nashville’s nightlife with a vintage twist, perfect for those who love a good story, a stylish setting, and a little mischief.

The Sum Up

The Nashville Speakeasy Secrets Roaring 20s Cocktail Crawl stands out as a lively, stylish way to explore the city’s hidden bars while learning about its lively Prohibition past. The balance of storytelling, authentic venues, and social fun makes it an excellent choice for anyone wanting a unique, memorable night out that mixes history with glamour.

If you appreciate good value, enjoy dressing up, or simply love a good cocktail and story, this tour offers a playful, engaging experience. The two-hour format is perfect for a relaxed evening, and the pay-as-you-go drinks mean you can customize your experience without feeling pressured.

Overall, it’s a fantastic way to see Nashville’s secret side, meet new friends, and toast to the roaring days of the 1920s in style. Whether you’re a history lover, a nightlife enthusiast, or just looking for a fun night out, this experience delivers a memorable night full of laughs, vintage charm, and stories that’ll keep you talking long after the last toast.

FAQ

Is this tour suitable for non-drinkers?
Absolutely. You can enjoy the storytelling, photos, and social atmosphere without ordering alcohol. The tour is about fun, history, and style, not just drinks.

How much should I expect to pay for drinks?
Drinks are paid separately from the ticket price, allowing you to choose your favorites, whether a vintage cocktail or sparkling water. Carry cash or card for purchases.

What should I wear?
While costumes like Gatsby glam or flapper outfits are optional and encouraged for photos, comfortable shoes are essential for walking between venues. Dress weather-appropriate.

Is the tour accessible for people with mobility issues?
The walk is less than half a mile in total, making it manageable for most, but those with mobility concerns should consider the walking involved.

Can I join if I’m under 21?
No. You need to be 21 or older to participate, as alcohol is involved. A valid ID is required to join.

What happens if it rains?
The tour runs rain or shine, but it’s advisable to dress accordingly. Venues may have indoor space to keep you dry and comfortable.

How large is the group?
The tour typically operates with a minimum of four guests, and group sizes can vary, keeping the experience intimate and lively.

You can check if your dates are available here: