Infants and small children can ride in a pram or stroller
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Service animals allowed
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Public transportation options are available nearby
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Transportation options are wheelchair accessible
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All areas and surfaces are wheelchair accessible
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Not recommended for pregnant travelers
Cancellation policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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For a full refund, you must cancel at least 24 hours before the experience’s start time.
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Cut-off times are based on the experience’s local time.
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If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
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This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
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Any changes made less than 24 hours before the experience’s start time will not be accepted.
Become our Lokal Curator
Are you ready to turn your hobbies into a business?
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 host leads you to four downtown venues with stories of bootleggers, corruption, and clever workarounds that kept the spirits flowing.
Discover local venues with occasional tour-only specials.
Join a Jazz Age–steeped guide: historian, toastmaster, ringleader!
Snap Insta-worthy shots in hidden nooks & glam spots.
Discover 4 bootlegger-worthy venues!
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!
Meeting Points
Departure
170 4th Ave N
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!
Return
Rep. John Lewis Way North & Church Street
Final locations can vary but will be close to this intersection.
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 host leads you to four downtown venues with stories of bootleggers, corruption, and clever workarounds that kept the spirits flowing.
Discover local venues with occasional tour-only specials.
Join a Jazz Age–steeped guide: historian, toastmaster, ringleader!
Snap Insta-worthy shots in hidden nooks & glam spots.
Discover 4 bootlegger-worthy venues!
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!
Meeting Points
Departure
170 4th Ave N
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!
Return
Rep. John Lewis Way North & Church Street
Final locations can vary but will be close to this intersection.
Itinerary
1
Downtown Nashville
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
2
Printer's Alley
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.
