A Closer Look at Bootleg & Barrels: A Tennessee Whiskey Tasting Experience
If you’re heading to Nashville and love a good story with your sip of whiskey, Bootleg & Barrels offers a fun, authentic journey through Tennessee’s clandestine past. For just $38 per person, this 2-hour walking tour takes you deep into Nashville’s Prohibition-era underworld, revealing the tales of gangsters, moonshiners, and the city’s hidden spirits scene. Led by knowledgeable guides trained in whiskey tasting, you’ll visit some of Nashville’s most iconic and secretive bars, enjoying curated pours of Tennessee’s finest.
What we especially appreciate about this experience is the blend of storytelling and tasting—it’s not just a drink experience but a lively history lesson, delivered with humor and flair. The fact that it’s a small-group tour means you can ask all your burning questions and get personalized attention, making it a more meaningful dive into Nashville’s boozy past. Plus, the tour’s focus on true crime and Southern folklore makes it appealing even if you’re not a whiskey aficionado but love stories of scandal and rebellion.
The main consideration is that alcohol consumption is optional, and you should be prepared to purchase drinks at each bar if you choose to indulge. Also, since the experience involves some walking through Nashville’s streets, comfortable shoes are recommended. This tour is best suited for adults over 21 who enjoy a mix of history, storytelling, and a good drink—or just a good story to go with their drink.
If you’re curious about Nashville’s hidden past, love small-group experiences, or want to combine history with a little tipple, this tour will suit you well.
You can check availability for your dates here:Key Points
- Authentic Nashville history: Focuses on Prohibition-era stories, gangsters, and moonshiners.
- Expert guides: Knowledgeable, engaging storytellers trained in whiskey tasting.
- Small-group intimacy: Personalized experience, perfect for questions and interaction.
- Visit iconic and hidden bars: Includes secret speakeasies and historic tasting rooms.
- Curated tastings: Enjoy Tennessee spirits, with options to purchase your own drinks.
- Flexible cancellation: Cancel up to 24 hours in advance for a full refund.
A Detailed Look at the Bootleg & Barrels Experience
What is the Tour All About?
Bootleg & Barrels isn’t just about tasting whiskey; it’s a curated walk through Nashville’s shadowy past, evoking the days when outlaws and lawmen clashed in smoky back rooms. Your guide, whose expertise is rooted in both whiskey and local lore, leads you through a series of historically significant and secretive bars, each with its own story to tell. These establishments range from famous old haunts to hidden speakeasies that once served as hubs for illegal distilling and bootlegging.
This experience is designed to give you a sense of Nashville’s gritty underbelly, with stories of murder, betrayal, and political corruption woven seamlessly into the narrative. The tour runs roughly two hours, typically in the afternoon or evening, making it a perfect way to kick off or wind down your day.
The Itinerary Breakdown
Meeting Point is at the Standard Proof Whiskey Company lobby, where you’ll gather your group and meet your guide—an individual who combines a knack for storytelling with professional whiskey tasting skills. From here, the tour wends its way through Nashvilles’s historic streets, visiting several bars and tasting rooms.
Each stop offers a curated pour of Tennessee spirits, with the guide sharing stories behind each distillery or bar. You might learn about underground distillers who evaded revenuers, or hear about powerful families controlling Nashville’s liquor trade during Prohibition. The narrative often includes true crime tales and local folklore, making the experience as much about storytelling as about the drinks.
More Great Tours NearbyWhat to Expect at Each Stop
- Historical context: The guide shares vivid stories about Nashville’s dark past, including scandals and gangsters operating in the shadows.
- Authentic bars: Expect to visit both well-known and secretive venues, some of which might be off the typical tourist path.
- Tasting experiences: You’ll sample curated pours—the specific spirits aren’t detailed but include some of Tennessee’s finest. You’re welcome to purchase additional drinks at each bar.
- Interactive storytelling: The guide encourages questions, adding humor and details that bring history alive.
Authenticity and Value
Reviews highlight how knowledgeable guides make all the difference. One traveler from Canada shared, “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,” emphasizing the personalized nature of the experience.
Another review praised the entertaining storytelling, noting that the guide was “the best guide ever,” which suggests that personality and expertise are key ingredients here. The small size of the tour means you get more personalized attention and a more relaxed atmosphere.
The Drinking Element
While tasting is not included in the price, you’re given the opportunity to purchase drinks at each venue, often with special deals or discounts. The Standard Proof Whiskey Company stop was particularly well-reviewed, with one guest describing the experience as “excellent,” although they felt that eight half-ounce shots might have been a bit much to start with, especially for those not used to sipping spirits.
Who Will Love This Tour?
This experience is perfect for history buffs, true crime fans, and whiskey lovers alike. The stories of gangsters and speakeasies appeal to those interested in Nashville’s less-glamorous past, while the curated tastings and engaging guides make it appealing for anyone wanting a more personalized and authentic bar-hopping experience. It’s also a fantastic choice for couples or small groups wanting a fun, intimate, and educational experience.
Why This Tour Offers Great Value
At just $38, this tour provides more than just a few drinks; it’s an insightful journey into the city’s hidden past. The combination of expert storytelling and curated tastings means you’re paying for access and knowledge more than just alcohol. Plus, with free cancellation up to 24 hours beforehand, it offers flexibility if your plans change.
Practical Tips
- Dress smart casual—bars are upscale and Prohibition-inspired, so avoid distressed or beachwear.
- Bring ID proving you’re 21 or older.
- Feel free to purchase additional drinks at each bar; the tour is about stories and spirits.
- Wear comfortable shoes—Nashville’s streets are best explored on foot.
- Consider tiping your guide if you enjoy the experience—guides often go above and beyond.
Final Thoughts
Bootleg & Barrels offers a unique blend of history, storytelling, and spirits in Nashville. It’s especially ideal for those who enjoy small-group experiences with knowledgeable guides and a focus on local lore and true crime. The tour’s charm lies in its ability to make history come alive with humor and authenticity—all with a glass in hand.
If you’re looking for a fun, educational, and slightly mischievous way to spend an evening in Nashville, this tour will fit the bill, particularly if you appreciate authentic venues and stories that aren’t part of the standard tourist fare.
FAQs
- Is this tour suitable for non-drinkers?
Yes. Drinking is optional, and you can enjoy the stories without purchasing alcohol. - Do I need to make a reservation?
Yes, it’s best to reserve in advance, especially during busy seasons. - What should I wear?
Dress smart casual; avoid distressed clothing or flip-flops as bars are upscale and Prohibition-themed. - Can I purchase more drinks during the tour?
Absolutely. Each bar sells drinks where you can decide how much to indulge. - Is the tour wheelchair accessible?
The provided information doesn’t specify, but since it involves walking through streets, it’s best to contact the provider for specific accessibility questions. - What is the meeting point?
In the lobby of the Standard Proof Whiskey Company. - How long does the tour last?
About 2 hours. - Is gratuity included?
No. It’s customary to tip guides if you’re happy with the experience. - What is the minimum age to participate?
Participants must be 21 or over.
To sum it up, Bootleg & Barrels provides an engaging, authentic look into Nashville’s bootlegging past with a lively group, expert guides, and compelling stories. It’s a fantastic choice whether you’re a whiskey enthusiast or just love a good tale of rebellion. Expect a fun, informative, and spirited experience that’s as memorable as it is educational.
You can check availability for your dates here: