Bootleg & Barrels: A Tennessee Whiskey Tasting Experience

Nashville isn’t just about country music; it has a gritty, smoky side steeped in Prohibition-era intrigue, moonshine legends, and secret speakeasies. The Bootleg & Barrels tour offers a chance to explore this shadowy part of Tennessee’s history while sampling some of the state’s finest whiskeys. If you’re a fan of good stories, great spirits, or both, this tour might just hit the spot.

What we love about this experience is the expert guidance—the tour is led by knowledgeable storytellers who are trained in whiskey tasting, making it both educational and entertaining. Plus, the exclusive access to some of Nashville’s best hidden tasting rooms elevates the experience beyond your average bar crawl. On the flip side, it’s a walking tour that involves some weather exposure and is best suited for those comfortable with a bit of physical activity.

This tour is perfect for whiskey enthusiasts, history buffs, or anyone curious about Nashville’s colorful past during Prohibition. It’s a smart choice for those looking for an authentic, intimate taste of the city’s secretive side, combined with the chance to sip top-quality Tennessee spirits.

Expert Guides: Knowledgeable storytellers trained in whiskey tasting bring the history to life.
Unique Access: Visit some of Nashville’s most iconic and hidden tasting rooms.
Historical Stories: Learn about Prohibition, moonshiners, and Nashville’s dark past in a lively manner.
Authentic Experience: A balanced mix of true crime tales, folklore, and spirits.
Value for Money: For $38, you get a two-hour, immersive journey with personalized storytelling.
Age Restrictions: Only 21+ to consume alcohol, but the tour itself is suitable for all curious history lovers.

Introduction to the Tour

We haven’t taken the tour ourselves, but the reviews and descriptions paint a compelling picture. This brand new experience presents itself as a spirited walk through Nashville’s underground alcohol scene and its notorious history. For those who enjoy delving into local lore with a glass in hand, this tour ticks all the boxes.

Two things stand out: the expert guidance that makes the stories come alive, and the exclusive access to historic and secretive bars. These are rare opportunities that add a sense of intimacy and authenticity. The only consideration might be the walking aspect—be prepared for some weather, and dress accordingly for a more refined bar setting.

If you’re someone who loves a good story, appreciates quality spirits, or simply wants an unusual lens on Nashville, this tour is ideal. It’s especially suited for travelers who enjoy small group experiences and a good mix of history and tasting.

You can check availability for your dates here:

What’s Included—And What’s Not

At $38 per person, this tour offers a well-priced 2-hour journey. Your ticket includes a walking tour with a knowledgeable guide who’s trained in whiskey tasting and storytelling—think of it as a lively history lecture with a spirited twist.

However, the alcoholic beverages are not included in the ticket price. You’ll have the option to purchase drinks at each bar, which are set by the venues themselves. This allows for some flexibility depending on your budget and preferences. The tour emphasizes an immersive experience rather than just a tasting, so expect plenty of engaging stories along the way.

Gratuity for the guide isn’t included, so it’s courteous to tip if you enjoyed the experience.

Itinerary and Highlights

The tour starts in the lobby of the Standard Proof Whiskey Company, a fitting starting point given its focus on Tennessee spirits. From there, the journey takes you through some of Nashville’s most iconic and hidden tasting rooms. Each stop offers curated pours and stories that paint vivid pictures of the black market whiskey trade, political corruption, and gangsters involved in Nashville’s liquor scene during Prohibition.

Expect to hear about underground distillers who dodged revenuers, powerful families controlling Nashville’s booze trade, and the murder and betrayal that often accompanied these illicit dealings. One reviewer appreciated the personalized nature of the tour, noting, “We had the opportunity of having a tour just for us,” which allowed questions and informal conversations to flourish.

The last stop, the Standard Proof Whiskey Company, offers a flight tasting—a selection of half-ounce pours that, according to one reviewer, was excellent but a bit much to start with. This part of the tour also leaves room for enjoying some beverages at your own pace, making the experience both educational and relaxed.

Authenticity and Atmosphere

The stories told during the tour are lively and detailed, blending true crime, folklore, and alcoholic history. The guides do a strong job of balancing fact with entertainment, ensuring you leave with a greater appreciation for Tennessee’s whiskey and its colorful past.

There’s an undeniable charm in exploring Nashville’s secret bars and hidden corners—these places often retain an air of nostalgia and rebellion. The tour’s focus on Prohibition-era legends and scandals makes it feel like stepping into a gangster movie, with plenty of local flavor.

Value and Practicalities

At $38, this tour offers substantial value for an experience that combines history, storytelling, and spirits. The chance to hear local legends from an expert guide** transforms a simple bar crawl into a memorable journey. Plus, given the reviews praising the guides’ knowledge, you’re likely to leave with more than just a buzz—you’ll walk away with stories to tell.

It’s a walking tour, so comfortable shoes and weather-appropriate clothing are advised. The tour usually lasts about two hours in the afternoon or evening, making it a perfect mid- or early-evening activity.

Who Will Love This Tour?

This experience is best suited for history enthusiasts, true crime fans, and spirits connoisseurs alike. It’s ideal for travelers who appreciate small-group, personalized experiences and enjoy learning in an informal setting. It also suits those curious about Nashville beyond the country music scene, particularly the darker, rebellious side of its past.

If you’re looking for a casual, engaging activity that combines storytelling with a taste of local spirits, this tour won’t disappoint. However, it’s not suitable for anyone under 21 or those looking for a laid-back, non-physical experience.

Bootleg & Barrels offers a lively, authentic glimpse into Nashville’s prohibition-era chaos. With expert guides, exclusive access to hidden bars, and compelling stories of gangsters, betrayal, and moonshine, the tour stands out as a unique way to experience Nashville’s more clandestine side. It’s a smart choice for curious travelers wanting a mix of history, culture, and spirits without the fluff.

The value is high for the price, especially considering the personalized stories and the chance to explore some of Nashville’s clandestine drinking spots. Whether you’re a whiskey lover or a history buff, this tour is a fun, informative, and spirited addition to your Nashville itinerary.

Overall, if you’re after an engaging, authentic look at Nashville’s shadowy past and enjoy a good story with your drink, Bootleg & Barrels is well worth your time. Just remember to dress sharp and come thirsty.

Is alcohol included in the tour price?
No, the tour price of $38 does not include alcoholic beverages. You can purchase drinks at each bar, with prices set by the venues.

Are there age restrictions?
Yes, all participants must be 21 or over to consume alcohol, though the tour itself is open to anyone interested in the stories.

What should I bring?
Bring government-issued ID to prove your age, an umbrella in case of rain, and gratuity for your guide if you enjoyed the experience.

How long is the tour?
The tour lasts approximately 2 hours and is typically offered in the afternoon or evening.

Where does the tour start?
It begins in the lobby of the Standard Proof Whiskey Company.

Is this a walking tour?
Yes, expect to walk between tasting rooms in Nashville’s lively bar scene. Comfortable shoes are recommended.

Can I cancel?
Yes, you can cancel up to 24 hours in advance for a full refund.

Is the tour suitable for non-drinkers?
Absolutely—non-drinkers can enjoy the storytelling and historical aspects; just remember that tasting is optional.

You can check availability for your dates here: More Great Tours Nearby