A golf cart tour with serious whiskey vibes. This one strings together three tasting rooms plus a speakeasy-style finish for a side of Nashville that’s more story than skyline. I like the mix of flavor-focused stops and neighborhood context, and I also like that your guide builds in lots of time for questions.

Two hours is short, though, so it rewards people who enjoy conversation and don’t need a long sit-down. One watch-out: there have been reported cases where plans shifted close to start time and the whiskey tasting didn’t happen the way people expected, so it’s smart to confirm day-of details.

Why This Tour Works for Whiskey Lovers

• Three tastings in one night: You visit multiple premium rooms, keeping your $34.95 ticket focused on access rather than alcohol cost.
• Speakeasy energy, not just bars: The story arc moves from Printer’s Alley’s old-school trouble to a cigar-bar inspired stop that ties into Tennessee whiskey lore.
• Good question time: With dedicated stops, you’re not stuck on mute while the group moves on.
• Business casual keeps it from feeling chaotic: The dress code can be a hassle, but it also tends to keep the vibe orderly.
• Small-group feel inside a max-100 tour: Even though the cap is high, the experience is designed around structured stops rather than a free-for-all.

Bootleg and Barrels in Nashville: A Golf Cart Night That Blends Whiskey and Street Stories

Nashville can feel like two cities at once. There’s the music-scene shine, and then there are the older blocks where bootleggers and speakeasies once quietly did business. This tour leans into that second side, using a golf cart to move efficiently and then handing you the street-level details where they matter.

At the core, you’re doing a whiskey tasting route with an explanation layer. The guide isn’t just pointing at buildings; you get context for what you’re seeing and why those places mattered to Tennessee whiskey’s wider story. It’s a fun format if you like learning while you socialize, not if you prefer a quiet, self-paced tasting.

You’ll also be part of an active group experience. The tour is built around people who want to talk—about flavors, about history, about what to order next—so the vibe works best when you’re game to chat.

Price and Value: What $34.95 Covers (and What It Doesn’t)

The ticket price is $34.95 per person for about two hours. That number is a good value if you look at it as paying for access to tasting rooms and guided storytelling—not for drinks.

Here’s the practical breakdown:

• The stops include tastings at three premium locations.
• Alcoholic beverages and tastings are not included in the ticket price. You’ll buy drinks separately at each location.
• You should plan for an extra amount for your pours, especially if you want to taste more than one option.

This matters because whiskey tastings can get expensive fast if everyone in your group orders multiple flights. If you keep it simple—one tasting flight per room, maybe one extra drink—you’ll likely feel good about the spend. If you try to “complete everything” at every stop, your total will rise quickly.

The tour also doesn’t include gratuity for your guide. If you enjoy the story delivery and explanation (and most people do), build a tip into your budget.

The Route You’ll Follow: Standard Proof to The Ariston

This experience runs as a chain of four stops, starting at Standard Proof Whiskey Co. and ending at The Ariston. In between, you’ll cover both tasting rooms and Nashville’s Printer’s Alley area, which was known for speakeasies and gaming houses.

You get set time at each location—about 30 minutes per stop—so you don’t lose the night to long lines or wandering. The format is ideal for visitors who want a full experience without it turning into a full evening commitment.

Stop 1: Standard Proof Whiskey Co. (In Order to Start Strong)

Your first tasting room is Standard Proof Whiskey Co., where you’ll sample infused whiskies. The standout here is variety: you’re not only tasting standard profiles, you’re trying flavors described as unlike any whiskey you’ve had before.

Why it’s a smart opener:

• You get a baseline for what the rest of the night will taste like.
• Infused styles make it easier for non-experts to discuss what they enjoy, even if they’re new to whiskey.

Possible drawback to keep in mind: if you’re the kind of taster who likes traditional, straight whiskey only, the infused focus might feel limiting. You can still find what you enjoy, but your expectations should match the concept of the first stop.

Stop 2: Nashville Barrel Company Distillery (Built for Quality Since 2018)

Next up is Nashville Barrel Company Distillery. This place was founded in 2018 by a small group of friends with a mission to offer the best whiskey and share their love for quality spirits.

What you’ll get from this stop:

• Another structured tasting experience in a distillery setting.
• A chance to compare how different production approaches translate into flavor.

Why this stop matters on a tour like this: tasting rooms feel similar until you notice the differences. Two rooms back to back help your palate learn fast. It also makes the next phase—walking and story—feel less random, because you’re already in “whiskey mode.”

Drawback: since alcohol isn’t included, your taste experience depends partly on what you choose to buy for your tastings. If you only sample one thing here, you’ll get less comparison value.

Stop 3: Printer’s Alley (Where the Stories Get Dark)

Then you shift from tasting rooms to a street tour through Printer’s Alley. This is where you slow down a little, look at the space, and hear about the darker side of Nashville—speakeasies and gaming houses in an era when bootlegging and backroom deals were part of the nightlife.

This stop is valuable because it anchors the whiskey theme in place. It’s one thing to taste spirits; it’s another to understand why people sought out hidden drinking spots in the first place. If you enjoy true crime-style storytelling or just like learning what happened behind the scenes, this is where you’ll feel the most “Nashville-specific” payoff.

Possible consideration: Printer’s Alley is story-forward, not a museum-style stop with lots of standing time. You’re likely to do some walking along the way, so it helps if you’re comfortable moving for short stretches.

Stop 4: The Ariston Speakeasy-Inspired Cigar Bar (Tennessee Whiskey Comes Full Circle)

Your final stop is The Ariston, a speakeasy-inspired cigar bar. This is where you tie back into Tennessee whiskey history with a fun end-of-night atmosphere.

Why the ending works:

• Speakeasy style fits the bootleg concept of the tour.
• It’s a natural place to linger and decide what you’d want to order if you were coming back on your own.

This last stop also functions as a “last tasting chance,” so it can be a smart moment to try something you didn’t choose earlier. Since you’ll likely be more confident about your preferences by then, you can spend more intentionally.

Timing, Meeting Point, and How to Keep the Night Smooth

The tour is about two hours total, with each stop around 30 minutes. That tight structure is great for people with a packed itinerary. It also means you’ll feel the day’s pacing—arrive ready to move when the group does.

You start at:

• Standard Proof Whiskey Co.

219 Rep. John Lewis Way N, Nashville, TN 37219

You end at:

• The Ariston

508 Church St, Nashville, TN 37219

The tour also notes that it’s near public transportation, which is a plus if you don’t want to deal with parking in the middle of downtown. The ticket is mobile, and confirmation happens at booking time.

One practical tip: keep your plans flexible around timing changes. There’s been at least one reported situation where the schedule was adjusted later than expected, and the tasting portion didn’t match what people originally booked. You can’t prevent a change, but you can reduce stress by checking the day-of instructions carefully and staying ready to adapt.

Dress Code and ID Rules: The Stuff That Can Actually Derail Your Night

If you want the tour to run smoothly, follow the rules exactly. The event requires guests to wear business casual attire. Athletic gear and cargo shorts are not allowed.

The specifics:

• Men must wear a collared shirt and closed-toe shoes.
• You must show government ID proving you’re 21+. The policy is strict: no exceptions and no refunds.
• The guide reserves the right to turn someone away if they seem too “spirited” or not dress to code. No refunds.

This is one of those rare cases where “boring details” are actually worth taking seriously. If you show up in sneakers that don’t meet your definition of closed-toe, or you treat business casual like you’re still on vacation, you risk losing the night entirely.

So pack light, but pack right. If you’re staying in Nashville for nightlife, this dress code is easy to meet with a collared shirt, simple pants, and clean shoes.

Getting What You Want: Social Whiskey Fun vs. Traditional Tastings

This tour is designed for people who enjoy both conversation and structure. It’s a good match if you like:

• Asking questions during tastings
• Learning the stories behind places
• Meeting other whiskey lovers who are curious about flavors

It may not be perfect if you want a quiet, long-form guided tasting with deep technical instruction. The stops are timed, and you’ll be moving, so this is more “experience with tastings” than “education class.”

It’s also a good idea to think about what you mean by tasting. Since alcohol isn’t included, you’ll get the best results by deciding what to purchase at each stop. If you want maximum variety, consider one tasting flight plus one comparison drink. If you want to keep costs down, choose fewer pours and ask what’s most popular.

Alcohol Costs and Pace: Plan Your Spending and Your Tolerance

Even though the tasting rooms are part of the experience, your drinking spend is separate. That means your personal budget will decide how many tastings you actually do.

The upside of this setup is control:

• You can taste more if you’re feeling adventurous.
• You can keep it simple if you’re watching alcohol costs or your pace.

The pace is also worth noting. With multiple stops and a street story stop, you’re likely to feel the night move faster than a typical bar visit. If you’re sensitive to alcohol, eat beforehand and go slow at the first tasting room. That first stop can set the tone quickly.

Also, remember the guide can turn people away if the group’s vibe gets too rowdy. If you’re the designated driver or you’re just keeping it chill, that’s okay. Just stay within the tour’s spirit and dress expectations.

Who This Tour Suits Best (and Who Might Skip It)

This tour fits best if you want a guided whiskey outing that also shows you Nashville’s older night-life geography. It’s especially good for first-timers who feel like they’ve only seen one version of the city.

You’ll probably love it if:

• You’re interested in speakeasy stories and bootlegging-era atmosphere
• You want social time with other whiskey fans
• You like short, structured experiences with a strong theme

You might want to think twice if:

• Your main goal is traditional, straight whiskey only
• You need a fully flexible plan that can handle last-minute changes without stress
• You dislike downtown walking or moving between multiple stops

Should You Book Bootleg and Barrels: Tennessee Whiskey Tasting Golf Cart Tour?

If you want whiskey tastings plus story-driven Nashville, this is an easy yes. The price is reasonable for access and guidance, and the four-stop structure keeps the night focused. I’d book it with one condition: be ready to confirm the day’s details and respect the dress code and 21+ ID rules, because those are non-negotiables that can affect your outcome more than anything else.

If you’re traveling with friends who want a fun shared night, this also offers a strong payoff because you’ll spend time talking, comparing tastes, and hearing what those streets used to mean.

FAQ

How much does Bootleg and Barrels cost?

The tour costs $34.95 per person.

How long is the tour?

The duration is about 2 hours.

What’s included in the ticket price?

You’ll visit three premium tasting rooms with a guided experience led by a whiskey tasting expert. Alcoholic beverages and tastings are not included and are sold separately at each location.

Do I need to be 21 or older?

Yes. A government ID is required to prove you’re 21+. There are no exceptions.

What’s the dress code?

Business casual is required. Men must wear a collared shirt and closed-toe shoes. Athletic gear and cargo shorts are not allowed.

Where does the tour start and end?

It starts at Standard Proof Whiskey Co., 219 Rep. John Lewis Way N, Nashville, TN 37219, and ends at The Ariston, 508 Church St, Nashville, TN 37219.

Is alcohol included in the tasting?

No. Alcohol and tastings are sold separately at each location. Alcohol is not included in the ticket price.

You Might Also Enjoy

Clan Tour of Northern Whisky DistilleriesIrish Whiskey Museum: Whiskey Blending ExperienceWhistler Distillery Tour & Tasting ExperienceTopper’s Rhum Distillery Tour in St Maarten