Bootleg & Barrels: A Tennessee Whiskey Tasting Experience

Uncover Nashville’s Hidden Whiskey History in a 2-Hour Tour for $38

Bootleg & Barrels: A Tennessee Whiskey Tasting Experience offers a unique look into Nashville’s lively and illicit past, all while enjoying curated whiskey tastings. For just $38 per person, this 2-hour adventure takes participants through the shadowy days of Prohibition, combining history, storytelling, and spirits in some of Nashville’s most iconic and secretive drinking spots.

This brand new tour is perfect for whiskey enthusiasts eager to explore Tennessee’s legendary distilling heritage or anyone fascinated by the gangster, moonshiner, and music legend stories connected to Nashville’s past. The tour departs from the Standard Proof Whiskey Company and features an expert guide trained in whiskey tasting, ensuring a knowledgeable and engaging experience. While alcohol is not included in the price, attendees can purchase drinks at each bar, making this tour a flexible and fun way to enjoy Nashville’s nightlife.

You can check availability for your dates here:

Key Points

• Price and Duration: Only $38, lasting 2 hours, offers a deep dive into Nashville’s whiskey and Prohibition era.
• Expert Guidance: Guides are trained in whiskey tasting and storytelling, adding richness to each stop.
• Exclusive Access: Visit some of Nashville’s most iconic and hidden tasting rooms.
• Unique Stories: Learn about gangsters, moonshiners, and scandals from Nashville’s past, tied closely to the city’s liquor trade.
• Walk and Taste: The tour includes walking through historic bars and speakeasies, with curated pours of Tennessee’s finest spirits.
• Age Restriction: Participants must be 21+; alcohol tasting is optional.

Starting Point and Meeting Details at Standard Proof Whiskey Company

The tour begins at the Standard Proof Whiskey Company’s lobby, where all participants meet. This central location provides a convenient starting point for Nashville’s lively downtown scene. The meeting process is straightforward, and guides are ready to start the narrative straight away.

Since the tour is rain or shine, travelers should bring an umbrella if weather conditions require. The walking aspect means comfortable shoes are recommended, but the focus remains on enjoying Nashville’s whiskey ambiance and storytelling, not strenuous activity.

Exploring Nashville’s Dark Prohibition Past

Bootleg & Barrels offers more than just tastings; it’s a journey back to Nashville’s outlaw days. The tour highlights the city’s secret speakeasies and underground distillers who dodged revenue agents during Prohibition. Participants learn about scandals, betrayals, and political corruption that shaped Nashville’s liquor scene.

This adventure blends history with true crime tales, bringing to life the murderous dark past of Nashville’s liquor trade. Tour guides weave stories of gangsters, moonshiners, and music legends who played roles in Nashville’s underground alcohol trade, making each step both informative and entertaining.

Stops at Nashville’s Most Iconic and Hidden Tasting Rooms

Participants visit several bar stops, each with a distinct atmosphere and curated whiskey pours. These locations include famous bars as well as hidden speakeasies that played a part in the city’s illicit drinking during Prohibition. Each stop provides a chance to sample Tennessee’s best spirits and hear stories that connect the location to Nashville’s fin de siècle bootlegging era.

Standard Proof Whiskey Company is not just the starting point but also a highlight, offering a flight tasting of spirits that is often praised, although some reviews note the eight half-ounce shots can be quite a bit to start with. The stops are carefully selected to balance historic significance with quality tasting experiences.

More Great Tours Nearby

The Guide: Knowledgeable and Entertaining Storytellers

The tour’s success hinges on guides trained in whiskey tasting and storytelling. They serve as the storytellers, providing historical context, true crime tales, and Southern folklore that animate each stop. Review comments praise guides for being entertaining and well-informed, making the journey both educational and engaging.

Their ability to answer questions and share insider stories adds to the tour’s appeal. The guides’ personalities and depth of knowledge make the experience feel personalized and authentic.

Tasting Opportunities and Alcohol Purchase Options

While the tour price covers the walking experience and stories, alcohol tasting is not included in the cost. Attendees can purchase drinks at each bar, with options for exclusive deals on drinks available through the tour. The standard bars offer curated pours of Tennessee whiskey, moonshine, and other spirits from Nashville’s distilling tradition.

Reviewers note that the flight tasting at Standard Proof Whiskey Company is a highlight, but eight half-ounce shots can be quite a lot to start the evening. Drink options are adult and optional, respecting the 21+ age restriction.

Walking through Nashville’s Outlaw and Music Legends

The tour connects Nashville’s whiskey history with the musical culture that made the city famous. Stories involve Music City’s legendary families, moonshiners, and outlaw musicians who played roles in the city’s prohibition-era underworld. The combination of true crime, musical history, and spirits makes this experience appealing to a broad audience.

Participants walk through historic neighborhoods and hidden bars, gaining insight into how Nashville’s music and liquor scenes intersected during times of prohibition and beyond.

Practical Tips: Dress and Preparing for the Tour

Dress code emphasizes smart casual attire suitable for Prohibition-inspired bars—no ripped jeans, flip-flops, or beachwear. Men should wear collared shirts, and all should bring a government-issued ID proving they are 21 or over. Since the tour involves walking rain or shine, an umbrella is recommended.

Attendees should bring gratuity for the guide if they wish to show appreciation, as tips are not included. The tour is accessible for most, but physical mobility should be considered as it involves walking between stops.

Flexibility and Cancellation Policies

Booking the tour allows for flexibility—full refunds are available if canceled up to 24 hours in advance. The pay later option offers the flexibility to reserve without immediate payment, ideal for uncertain schedules. Since the tour operates mainly in the afternoon and evening, travelers can choose a time that suits their plans.

Comparing to Other Nashville Experiences

While there are many Nashville tours such as hop-on-hop-off trolleys or music show tickets, Bootleg & Barrels stands out for its focus on whiskey history and Prohibition stories. It offers a more intimate, story-driven experience with exclusive access to hidden bars and curated tastings.

This tour is particularly appealing to history buffs, spirits enthusiasts, and anyone interested in the darker stories of Nashville’s past. Its affordable price point makes it accessible without sacrificing depth or entertainment value.

Who Will Most Appreciate This Tour?

Whiskey lovers will enjoy the expert guide and the curated pours. History enthusiasts find the stories of Nashville’s bootlegging and crime captivating. The tour suits adults over 21 who are comfortable walking outdoors in various weather and want a combination of storytelling, history, and spirits. It may not be ideal for those seeking a large group or party environment since the experience is more personalized and narrative-driven.

Final Thoughts on Bootleg & Barrels

Bootleg & Barrels offers an engaging way to experience Nashville beyond the usual sights. For $38, the 2-hour guided walk provides a rich blend of history, true crime, and whiskey tasting in a setting that emphasizes storytelling and authenticity.

This tour’s highlight is its ability to combine Nashville’s outlaw past with its vibrant spirits scene. It’s an ideal choice for adults looking for a fun, educational, and flavorful experience that dives into the city’s darker and tastier side.

Frequently Asked Questions

Is the whiskey tasting included in the tour price?
No, tasting is not included but can be purchased at each location. There are special deals available if you choose to buy drinks during the tour.

What is the duration of the tour?
The tour lasts approximately 2 hours.

Where does the tour start?
It starts at the Standard Proof Whiskey Company lobby.

What should I wear?
Dress smart casual, suitable for Prohibition-inspired bars—no ripped or distressed jeans, flip-flops, or beachwear. Men should wear collared shirts.

Are children allowed?
No, the tour is for guests aged 21 and over due to alcohol consumption.

Can I cancel the tour?
Yes, full refunds are available if canceled more than 24 hours before the scheduled start.

Is alcohol optional?
Yes, drinking is optional. Participants can enjoy the stories and ambiance without purchasing drinks.

What makes this tour different from other Nashville experiences?
It combines history, crime stories, and spirits into a personalized walking tour that visits hidden bars and iconic locations.

Are guides knowledgeable?
Yes, guides are trained in whiskey tasting and storytelling, praised for their entertaining and informative approach.

Is the tour accessible?
The tour involves walking outdoors, so comfortable shoes are recommended, and mobility should be considered.

Can I book and pay later?
Yes, the reserve & pay later option allows you to book now and pay nothing until closer to the date.

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