Bootleg & Barrels: A Tennessee Whiskey Tasting Experience

Thinking about adding a whiskey-themed adventure to your Nashville trip? This Bootleg & Barrels tour promises a lively, insider look at Tennessee’s clandestine past, with plenty of stories and curated tastings along the way. It’s a fresh take on the typical bar crawl—more immersive, more storytelling, and tailored for those curious about the gritty history that shaped the city’s reputation for both music and moonshine.

What really caught our eye is how this tour combines expert-led storytelling with visits to some of Nashville’s hidden and iconic tasting rooms. Plus, the focus on the Prohibition era gives it a sense of adventure and mystery that’s perfect for history buffs and whiskey lovers alike. On the flip side, the tour’s 2-hour duration means it’s quick but packed, and it’s mainly focused on the experience of the stories and drinks, not just the drinks themselves.

This experience works well if you’re interested in local history, love learning about spirits, or just want a different kind of night out. It’s also quite good for those who appreciate guided insights from knowledgeable storytellers—and you’ll definitely want to be comfortable walking and standing in some historic bars. If you’re after a laid-back, casual tasting that’s more about the tales than the drinks, this might be just right.

Key Points

Expert Guides: Guides are trained in whiskey tasting and storytelling, adding depth and personality to the experience.
Historical Focus: It’s not just about drinking; it’s about Nashville’s secret past during Prohibition, gangsters, and bootlegging.
Unique Venues: You’ll visit some of Nashville’s best and most hidden whiskey tasting spots, making this a bit of a local’s secret.
Cost-Effective: At $38, the price offers good value for a 2-hour guided experience with storytelling—drinks are extra.
Age Restrictions: Only those 21+ can consume alcohol, but the tour itself is accessible to anyone interested in the history.
Flexible Booking: You can reserve now and pay later, with full cancellation allowed up to 24 hours in advance.
Personalized Experiences: Some reviews mention private or small group tours, which can make for a more intimate and flexible outing.
Weather-Ready: Tours are rain or shine, so dress appropriately and bring an umbrella if needed.

You can check availability for your dates here:

What to Expect from the Tour

The Bootleg & Barrels tour kicks off at the Standard Proof Whiskey Company, where you’ll meet your guide and begin your journey into Nashville’s bootlegging and speakeasy past. Over the next two hours, expect a walking tour through some of the city’s most iconic and hidden bars, each with its own story and atmosphere.

Your guide will share stories of gangsters, moonshiners, and corrupt officials who operated under the cover of darkness during Prohibition. These tales aren’t just told—they’re brought to life with vivid storytelling that ties into the city’s cultural fabric, including its legendary music scene.

Throughout the tour, you’ll enjoy curated pours of Tennessee spirits. While tasting isn’t included in the ticket price, you have the option to purchase drinks at each venue, and a special deal on all-inclusive drink packages might be available. Some reviewers mention that the tasting portion at Standard Proof Whiskey Company was excellent—though, for some, the eight half-ounce shots at once could be a lot to start with, so pace yourself.

You’ll get a chance to peek into the hidden bars and learn about their significance, as well as hear about Nashville’s dark, scandalous past—from political corruption to infamous brawls. The stories are engaging enough to keep your attention, whether you’re a true crime fanatic or just want to hear about Nashville’s rough-and-tumble history.

The Venues and Stops

While the exact stops may vary, you can expect visits to some of Nashville’s most celebrated and secretive whiskey spots. These places are chosen for their historic ambiance and connection to the era of Prohibition, giving you a real sense of what it was like to drink in those days.

The first stop usually sets the tone, offering an underground or speakeasy vibe. Each subsequent bar offers a different perspective—whether it’s a hidden gem or a well-known tavern with a storied past. The tour’s emphasis on storytelling over pure tasting means you’ll be encouraged to soak in the atmosphere and history as much as the drinks.

The Guides and Their Stories

One of the standout features, according to reviews, is the knowledge and entertainment value of the guides. Travelers have raved about guides who are not only well-versed in whiskey but also in delivering captivating stories. They help make the past feel immediate, connecting you to Nashville’s outlaw legends and scandalous past.

A reviewer from Canada mentioned, “We had the opportunity of having a tour just for us. We were able to ask our questions and get all the info we wanted,” highlighting the personalized touch some groups can enjoy. Others appreciated how guides blended history, crime stories, and local lore into a lively narrative.

Pricing and Value

At $38 per person, this tour offers a cost-effective way to explore Nashville’s whiskey history without feeling rushed. Considering the guide’s expertise and the exclusive access to hidden venues, it’s an affordable way to add depth to your night.

Keep in mind, the alcoholic beverages are not included in the price, but the opportunity to purchase drinks at each bar means you can tailor your experience to your preferences. The special deals on drinks can make it more economical if you decide to indulge. Some reviewers felt the tasting flights at the final stop were worth it, especially when combined with the storytelling.

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Who Should Consider This Tour?

This experience is ideal for whiskey lovers eager to learn about Tennessee’s distilling past, history buffs interested in Prohibition-era stories, or anyone wanting a more intimate, guided night out in Nashville. It’s also suited for travelers who enjoy small group experiences and are comfortable walking and standing in bars for a couple of hours.

Since the tour is 21+, it’s not suitable for children or those looking for family-friendly activities. But if you’re someone who appreciates good storytelling, historical context, and a taste of Nashville’s secret past, this tour will fit the bill nicely.

The Sum Up

Bootleg & Barrels offers a fascinating peek into Nashville’s clandestine past, blending history, storytelling, and whiskey in a way that’s engaging and memorable. The knowledgeable guides elevate the experience, making the stories vivid and real, which adds a lot of value—especially for those who enjoy learning while they sip.

The tour’s focus on hidden bars and Prohibition-era tales makes it perfect for travelers craving something different from the usual city tour. It’s especially suited for those who appreciate small group settings and want to deepen their understanding of Nashville’s gritty side.

While it’s not a full-blown tasting experience by itself, the options for purchasing drinks and the specially curated venues make it a worthwhile night out. The price point is reasonable, and the reservation flexibility adds peace of mind. If history and spirits are your thing, this could be a highlight of your Nashville trip.

FAQ

Is this tour suitable for people under 21?
No, only those 21 and over can consume alcohol, but the tour itself is open to all ages interested in the history.

What’s included in the tour?
You get a guided walking tour with a knowledgeable guide trained in whiskey tasting and storytelling. Drinks are not included but can be purchased separately.

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

How long is the tour?
It lasts approximately 2 hours, making it a great short excursion that packs in a lot of history and atmosphere.

Do I need to book in advance?
Yes, it’s recommended to reserve ahead, especially since you can choose to pay later and cancel if needed.

Where do we meet?
The meeting point is in the lobby of the Standard Proof Whiskey Company.

Is the tour rain or shine?
Yes, the experience runs in all weather, so dress appropriately and bring an umbrella if rain is forecasted.

What should I bring?
Bring government-issued ID to prove your age, and dress in smart casual attire suitable for high-end bars. An umbrella is also wise.

Would this be a good experience for solo travelers?
Absolutely. The guided nature and small group size make it easy to engage and meet fellow enthusiasts.

Whether you’re a serious whiskey enthusiast or just curious about Nashville’s bolder side, Bootleg & Barrels offers a unique, story-driven night that’s likely to leave you both educated and entertained.

You can check availability for your dates here: