Bootleg & Barrels: A Tennessee Whiskey Tasting Experience

If you’re headed to Nashville and craving a taste of its rebellious past, then Bootleg & Barrels offers a lively, informative look into Tennessee’s clandestine whiskey scene. This tour promises more than just a sip; it’s a window into the gritty, scandalous world of Prohibition, complete with stories of gangsters, moonshiners, and the city’s secret bars. It’s a chance to walk in the footsteps of outlaws and music legends alike, all while sampling some of the state’s finest spirits.

What makes this tour stand out? First, the knowledgeable guides who weave history and storytelling seamlessly, making each stop both educational and entertaining. Second, the exclusive access to some of Nashville’s best hidden tasting rooms — places many visitors wouldn’t stumble upon on their own. That said, the price of $38 per person is quite reasonable considering the depth of storytelling and the curated experience, but keep in mind that alcoholic beverages are purchased separately at each bar.

This experience is ideal for whiskey lovers, history buffs, or anyone curious about the colorful tales of Nashville’s Prohibition era. If you enjoy a good story paired with a splash of local spirits, this tour will keep you engaged. However, those looking for a more traditional, sit-down tasting might find the walking pace a bit brisk.

Key Points

• Expert Guides: Well-trained in whiskey tasting and storytelling, bringing history vividly to life.
• Hidden Gems: Access to Nashville’s best secret bars and historic tasting rooms.
• Themed Experience: Combines true crime, folklore, and Prohibition stories with spirits.
• Flexible Options: Walk-and-taste tour lasting 2 hours, usually in the afternoon or evening.
• Value for Money: At $38, it’s a cost-effective way to explore Nashville’s whiskey scene.
• Age Restriction: Must be 21+ to purchase alcohol, but tasting is optional.

You can check availability for your dates here:

A Practical Overview of the Experience

When considering a tour like Bootleg & Barrels, the details matter. This is a 2-hour guided walking journey starting in the lobby of the Standard Proof Whiskey Company. The meeting point is convenient, and the tour is designed to be rain or shine, so pack an umbrella if the weather looks uncertain. The tour leans heavily on storytelling — your guide, trained in whiskey tasting, will share tales of the outlaws, political corruption, betrayals, and brawls that once defined Nashville’s illicit liquor trade.

The tour isn’t just about drinking; it’s about understanding the culture behind the spirits. Each stop offers a curated pour of Tennessee’s finest, with the opportunity to purchase drinks at bars where the prices are set by each hotel. While tasting is not included in the tour price, you might find the overall experience worthwhile considering the exclusive access to historic bars and insightful stories.

One guest commented, “Our tour was a lot of fun as it was just my husband and me… we had a personalized tour with our guide,” highlighting the intimate, flexible nature of this experience. Another noted, “The guide was knowledgeable and entertaining,” confirming that the storytelling quality is a highlight.

The Itinerary and Its Highlights

The tour begins at the Standard Proof Whiskey Company, where you’ll meet your guide. From there, the journey takes you through some of Nashville’s most iconic and hidden bars with a Prohibition theme. You’ll learn about underground distillers dodging revenuers, the powerful families controlling Nashville’s liquor trade, and the notorious stories that have become local legends.

Each bar has its own character — some are historic establishments that have survived since bootlegging days, others are modern speakeasies inspired by the era. The curated pours are typically Tennessee whiskeys, giving you a taste of the state’s renowned spirits. The storytelling approach means that every sip is accompanied by colorful tales, making the experience both flavorful and educational.

The review from one traveler mentions the flight tasting at Standard Proof Whiskey Company was excellent but notes that “eight half-ounce shots was a bit too much to start with,” which suggests pacing is important. The tour is designed to be manageable, but pace yourself if you plan to sample several drinks.

Why This Tour Could Be Your Nashville Must-Do

This experience is perfect for those who want a more nuanced understanding of Nashville’s history through the lens of its whiskey trade. It’s especially suited for visitors who appreciate storytelling combined with a tasting rather than just a standard bar crawl. The mix of true crime, folklore, and alcohol makes it engaging, if somewhat niche.

Since the tour is walk-focused, comfortable shoes are a must. The two-hour duration is just right — long enough to immerse yourself without feeling rushed. The cost of $38 is quite reasonable for what’s included — access to exclusive bars, expert narration, and a glimpse into Nashville’s secret history.

But it’s worth noting that drinking is optional. If you prefer not to purchase alcohol or aren’t of age, the stories alone make this a worthwhile cultural experience. Plus, the flexibility to cancel up to 24 hours in advance adds peace of mind if your plans change.

Who Should Sign Up?

This tour best suits adventurous spirits, history buffs, or whiskey enthusiasts looking to add a bit of rebellious glamor to their Nashville trip. It’s also a good choice for small groups or couples wanting a personalized, intimate experience. If you’re keen on learning about Nashville’s Prohibition era in a fun, informal setting, this tour will hit the mark.

For those seeking a traditional tasting or family-friendly activities, this may not be ideal, as alcohol consumption is restricted to those 21 and over and tasting is not included in the tour price.

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The Sum Up

Bootleg & Barrels offers a lively, detailed introduction to Nashville’s hidden whiskey scene and its colorful past. The blend of expert storytelling, exclusive bar access, and curated drinks makes it a standout experience for anyone curious about the city’s rebellious spirit. The tour’s affordability, combined with its engaging guides, provides excellent value for those interested in history, spirits, or both.

This experience is especially perfect if you enjoy small-group, personalized tours with authentic storytelling. Whether you’re a whiskey connoisseur or just love a good story with your drink, you’ll likely find this tour both fun and enlightening.

For travelers who want more than a typical bar crawl — who are eager to connect Nashville’s past with its present — Bootleg & Barrels is a great choice that balances education and entertainment in a relaxed, approachable setting.

Frequently Asked Questions

Is this tour suitable for children or those under 21?
No, all participants must be 21 or over to purchase alcohol. Tasting is optional, but proof of age is required.

How long does the tour last?
The tour lasts approximately 2 hours, usually scheduled in the afternoon or evening.

Are alcoholic beverages included in the tour price?
No, tasting is not included. You can purchase drinks at each bar, and the prices are set by the bars themselves.

Where does the tour start?
The meeting point is in the lobby of the Standard Proof Whiskey Company.

Can I cancel the tour if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund.

Is there a dress code?
Yes, dress appropriately for a higher-end, Prohibition-inspired bar experience — no cut-offs or flip-flops.

What should I bring?
Bring government-issued ID, an umbrella if necessary, and gratuity for your guide if you wish to tip.

In all, Bootleg & Barrels offers a well-balanced look at Nashville’s clandestine past, perfect for lovers of spirits and stories alike. It’s an authentic, fun way to explore the city beyond the usual tourist spots, making it a good addition to any Nashville itinerary.

You can check availability for your dates here: