About this experience
Nashville’s Original Prohibition Cocktail Crawl explores downtown’s jazz-era nightlife, hidden-gem bars, and true stories from a sin-soaked past. Small groups and pay-as-you-go drinks keep it flexible, fun, and full of Gatsby-era mischief.
Please note: this is a Prohibition-themed cocktail crawl, NOT a speakeasy-only tour. Nashville does not have enough true speakeasies near each other to create a walkable route. Instead, we visit a curated mix of historic, hidden-gem, and era-inspired venues for history, cocktails, and lots of laughter.
In two hours, your 5-star host leads you to four downtown venues with stories of bootleggers, corruption, and clever workarounds that kept the spirits flowing.
Drinks are optional and à la carte; some venues may offer specials or preferred pricing, but discounts are not guaranteed at every stop. The walk is under a mile and relaxed—ideal for groups, couples, bachelorettes, and curious travelers who like cocktails with crazy-but-true history!
At a glance
- Duration: 2 hr 15 min
What is included
- Stroll sin-soaked streets & hear shocking-but-true tales.
- Discover local venues with occasional tour-only specials.
- Join a Jazz Age–steeped guide, toastmaster & ringleader!
- Snap Insta-worthy shots in hidden nooks & glam spots.
- Discover 4 bootlegger-worthy venues!
Not included
- Drinks & food – Pay as you go and ONLY buy what you want! Drinking is not required!
- Tips – Usual 20% (~$11.60) IF you have the fun we hope you do!
Itinerary and highlights
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.
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.
Meeting and pickup information
- 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!
Languages and tickets
- English — Guide
- Mobile Only
Tour operator
- Local Tastes of Nashville
Accessibility and practical details
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Not recommended for pregnant travelers
- Suitable for all physical fitness levels
Cancellation policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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