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108jenellepOctober 2026 • TripAdvisor
So much fun
We had such an incredible time!! Dean was amazing, funny, knowledgeable, and so much fun. Would absolutely recommend this tour (and Dean particularly!) to everyone!
Nashville’s 1st Prohibition Cocktail Crawl: Secrets & Scandals
4.8
51
Reviews
Recommended by 96% travellers
96% of guests rated this experience 4 stars or higher
4.8 (51)
Recommended by 96% travellers
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4.8
51
Reviews
Recommended by 96% travellers
96% of guests rated this experience 4 stars or higher
4.8 (51)
Recommended by 96% travellers
Earliest Date Available: November 6, 2026This experience is in high demand. Book now to lock in the next available date.
Free CancellationCancel for free up to 1 day before your experience
Food for HappinessFor every guest in your booking, we donate 10 meals to children around the world
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4.8
•51 reviews US$50.94 per guest
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Earliest Date Available: November 6, 2026This experience is in high demand. Book now to lock in the next available date.
Free CancellationCancel for free up to 1 day before your experience
Food for HappinessFor every guest in your booking, we donate 10 meals to children around the world
Why book with byFood?Japan's #1 food travel platform
Japan's #1 food travel platformTrusted by 50,000+ travelers worldwideCurated by food lovers, for food loversFeatured in CNN, Forbes & NYT
Description
Good to Know
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!
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!
Drinks & food – Pay as you go and ONLY buy what you want! Drinking is not required!
Gratuities
Tips – Usual 20% (~$11.60) IF you have the fun we hope you do!
1
30 minutes · Admission Ticket Free
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.
THE MEN’S QUARTER Nashville’s most notorious playground — where the booze poured freely, the dice an…
2
30 minutes · Admission Ticket Free
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.
Dare to duck into Nashville’s most notorious back alley! Step into history (and maybe a little troub…
Meeting Point
170 4th Ave N, 4th Avenue North, Davidson County Tennessee, United States, US, 37219
Open in Google MapsMeet 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!
End Point
Rep. John Lewis Way North & Church Street, Davidson County Tennessee, United States, US, 37219
Open in Google MapsFinal locations can vary but will be close to this intersection.
Free cancellation
Cancel up to 1 day before for a full refund.
No refund within 1 day of the experience or no-shows.
4.8
51 reviews
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+29 photos51 reviews
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kathrynz210October 2026 • TripAdvisor
Prohibition Cocktail Tour
Drew and Ashley were great tour/hosts! I really enjoyed learning about prohibition in Nashville. They were very knowledgeable and kind!
V
Response from ViatorOctober 26, 2026
Thanks for joining us! Nashville has some crazy history. We hope to see you again.
M
mckennab866October 2026 • TripAdvisor
Best tour guide
We had a blast! Dean was a great host!
V
Response from ViatorOctober 14, 2026
We're so glad you had a good time! Thanks for the shout-out to Dean.
R
R2242LNheatherlOctober 2026 • TripAdvisor
Perfect night out
This was one of the best things we did on our trip. Very informative, fun and so awesome to check out the different places. Drew was amazing and we had an incredible time!
V
Response from ViatorOctober 12, 2026
Wow, nice to read this! It was a pleasure to share Nashville with you.
K
katarinas2019October 2026 • TripAdvisor
FREAKING AWESOME TOUR!!
Absolutely 💯 awesome!! My sister and I had a wonderful time!! The stories about bars and history were freaking awesome!! We appreciate you Drew!! More than you know!! Thank you for a wonderful tour!!
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Response from ViatorOctober 12, 2026
We'll let Drew know! So great to have you all on the tour. We appreciate you, too!
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