Nashville Prohibition Vintage Cocktail Crawl

Explore the clandestine world of the 1920s with Nashville’s ORIGINAL Prohibition vintage cocktail crawl. Over two hours, visit four unique venues, from glamorous lounges to hidden hideaways, each serving authentic cocktails and sharing jaw-dropping true stories from the era. Your host will keep the energy high and the tales scandalous as you sip through this unforgettable experience. Perfect for bachelorettes, birthdays, couples, and history buffs, this tour puts a stylish spin on Nashville nightlife with an optional upgrade to a secret cigar lounge for the ultimate speakeasy finale.
● Discover four hidden bars with authentic 1920s cocktails
● Hear true Prohibition tales—no tourist-trap fluff
● Optional upgrade for access to an exclusive speakeasy cigar lounge
● Ideal for groups seeking a fun, stylish, one-of-a-kind night out

Meeting Point

170 4th Ave N

170 4th Ave N, Nashville, TN 37219, USA

Meet your host OUTSIDE the hotel — Look for someone with some Jazz-era flair — We're looking for you, too!
NOTE: Our 1:30 PM Tours, meet outside The Hotel Indigo/Countrypolitan (315 Union St)

HOT TIP: Arrive 20–30 minutes EARLY for pre-tour cocktails at exclusive “Gatsby Insider” pricing!

What's included:

• 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.

Not included:

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

What to expect:

Duration: 2 hours

Downtown Nashville

, , Nashville, 37219, Tennessee

THE MEN’S QUARTER
Nashville’s most notorious playground — where the booze poured freely, the dice and the patrons could both be loaded, and the cops on the beat knew the word on the street... and looked the other way!
SMOKEY ROW
Once a blurry-eyed haze of cigars, fallen souls, and back-room brawls — the air thick with mischief, moonshine, and whispers you didn’t dare repeat.

THE INTERSECTION OF “SIN & SALVATION”
Where the shadows of church steeples fell across gin joints and hooch houses, and bells mingled with the calls from “Cat Houses.” Proof this town’s halos and highballs have always shared the same streets.

Walk these streets with us and you’ll begin to FEEL the echoes of the time — and maybe even the seductive pull a little sin can have for the saintly.

30 minutes

Printer's Alley

Between 3rd Ave N & 4th Ave N, An alley from Union St to Commerce St, Nashville, 37201, Tennessee

Dare to duck into Nashville’s most notorious back alley!
Step into history (and maybe a little trouble) in the legendary Printer’s Alley — where the hooch flowed, the jazz jumped, and the coppers knew to mind their own business.

By day, it was a hub for printing presses and bible-binding. But by night? A Prohibition playground for gangsters, politicians, and high-rollers slipping past the law for bootleg whiskey and hot music.

Today, the shadows still hum with speakeasy-style bars, sultry blues clubs, and hidden nooks that keep its glamorous, slightly scandalous spirit alive.

Walk here with us, and feel why Nashville’s legendary past — and its coolest locals — still choose this strip for nights a little edgier (and more historic) than Honky Tonk Row.

30 minutes