• 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.
• Unlock “Gatsby Insider” discounts at our exclusive vintage 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

Delve into the secretive realm of the 1920s with Nashville’s ORIGINAL Prohibition vintage cocktail tour. Over the course of two hours, explore four distinct venues, ranging from opulent lounges to concealed retreats, each offering genuine cocktails and sharing astonishing true stories from the period. The host will maintain a lively atmosphere and share scandalous tales as participants enjoy this memorable adventure. Ideal for bachelorettes, birthdays, couples, and history enthusiasts, this tour adds a chic twist to Nashville’s nightlife with an optional upgrade to a hidden cigar lounge for the ultimate speakeasy conclusion.

● Explore four secret bars with genuine 1920s cocktails
● Listen to true Prohibition stories—no tourist-trap nonsense
● Optional upgrade for entry to an exclusive speakeasy cigar lounge
● Perfect for groups looking for a fun, stylish, unique night out

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