• Downtown Nashville - THE MEN’S QUARTER
  Nashville’s infamous playground — where drinks flowed abundantly, dice and patrons were often loaded, and the streetwise officers turned a blind eye to the happenings!

SMOKEY ROW
Once a foggy haze of cigars, lost souls, and secretive scuffles — the air was thick with mischief, moonshine, and whispers best left unspoken.

THE INTERSECTION OF “SIN & SALVATION”
Where church steeple shadows fell over gin joints and speakeasies, and bells mingled with calls from “Cat Houses.” This town has always seen halos and highballs share the same streets.

Join us on these streets and you’ll start to FEEL the echoes of the past — and perhaps even the alluring temptation a little sin can have for the virtuous.

• Printer’s Alley - Dare to venture into Nashville’s most infamous back alley!

Step into history (and perhaps a bit of mischief) in the iconic Printer’s Alley — where the liquor flowed, the jazz thrived, and the police knew to look the other way.

By day, it was a center for printing presses and bible-binding. But by night? A Prohibition haven for gangsters, politicians, and high-rollers evading the law for bootleg whiskey and lively music.

Today, the shadows still resonate with speakeasy-style bars, sultry blues clubs, and hidden corners that maintain its glamorous, slightly scandalous spirit.

Join us here, and discover why Nashville’s storied past — and its coolest locals — still favor this strip for nights a bit more daring (and historic) than Honky Tonk Row.

• Stroll sin-soaked streets & hear shocking-but-true tales.
• Join a Jazz Age–steeped guide: historian, toastmaster, ringleader!
• Snap Insta-worthy shots in hidden nooks & glam spots.
• Enjoy insider specials at select partner venues.
• Discover 4 hidden-gem, Prohibition-inspired bars & lounges.

• Drinks & food – Pay as you go and ONLY buy what you want! Drinking is not required!
• Gratuities

Nashville’s ORIGINAL Prohibition cocktail tour delves into jazz-era venues, hidden bars, and fascinating true stories from a colorful past. With small groups, local guides, and pay-as-you-go drinks, the experience remains enjoyable and adaptable.

In about two hours, participants will explore four handpicked locations in downtown Nashville, each chosen for its Jazz Age ambiance and ties to Prohibition. Expect a blend of insider, era-themed spots and select speakeasy-style locations.

Revel in the captivating history as you sip and stroll. Discover true stories of daring flappers, ingenious bootleggers, surprising enforcers, and the clever tactics that kept the drinks flowing.

Drinks are chosen by you and paid as you go, ensuring you remain in control. Groups are kept small, the walking distance is less than a mile, and the pace is leisurely. Perfect for bachelorettes, birthdays, couples, and curious travelers seeking a unique experience with style and depth.

For a full refund, cancel at least 24 hours before the scheduled departure time.