X
Family Fun
I must say this tour was Awesome! Dean is the man! Very knowledgeable and funny. I highly recommend this tour, me and my family had such a blast.
Operator response
We're so glad to hear that! Thanks for bringing in your group.
Nashville’s 1st Prohibition Cocktail Crawl: Secrets & Scandals
+10 photos
At a glance
- Duration
- 2h 15min
- Price from
- $48 / person
- Rating
- 4.9 / 5 · 41 reviews
- Languages
- EN
- Group
- Small group, up to 14
- Cancellation
- Free cancellation
- Meeting point
- 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!
- Confirmation
- Instant
Prices checked on Sep 11, 2026Things to do in Nashville
Description
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. 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!
Tour Options
Itinerary
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.
Highlights
Stroll sin-soaked streets & hear shocking-but-true tales.
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!
What's included
Included
Stroll sin-soaked streets & hear shocking-but-true tales.
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!
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!
Traveller Ratings
4.9
41 reviews
Important Information
- 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
Frequently asked questions
How long does this tour take?
Nashville’s 1st Prohibition Cocktail Crawl: Secrets & Scandals lasts about 2h 15min. The itinerary has 2 stops.
How much does this tour cost?
Prices start at $48 per person for this Nashville experience, booked through Viator with the price shown before checkout. There are 2 booking options, so the final price depends on the option you choose.
Can I cancel this tour for free?
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
Where does the tour start?
The meeting point is 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!. Hotel pickup is not part of this experience.
What languages is this tour offered in?
The experience is available in EN.
Is this a private or a group tour?
It is a small-group experience with a maximum of 14 participants.
Is the tour suitable for children?
Infants and small children can ride in a pram or stroller
Is the tour wheelchair accessible?
Wheelchair accessible Transportation options are wheelchair accessible All areas and surfaces are wheelchair accessible
Reviews(41)
C
Nashville
Drew was awesome and we had a great time!! Highly recommended tour with this young man
Operator response
We appreciate you!
J
Great time on this tour!
Three of my friends and I went on this tour with Jeff, it was excellent! All the information he shared in the fun facts was very much appreciated, he made it really interesting and engaging and provided great recommendations to us. But absolutely recommend for a group looking to do something different and have fun.
Operator response
It was a pleasure to have your group on the tour! Thanks so much for the comments.
B
Best guided tour of our vacation!
Drew was awesome, a blast to have as a guide and very knowledgeable. Would definitely book again.
Operator response
We'd love to see you again! We appreciate the comments.
S
great experience
drew was a great tour guide! he was funny and knowledgeable would highly recommend this tour!
Operator response
Thank you--we really appreciate the comments! So glad you joined us.
B
Perfect
Drew was an incredible tour guide and kept the crowd super entertained a very personable human!
Operator response
Drew loves to share Nashville. Thank you so much for joining our tour. We appreciate you!
1
Drew made this tour a blast!
Our guide Drew was funny, knowledgeable, and kept the group moving at a pace that felt intentional but never rushed. The tour struck a great balance between history and walking, with plenty of dedicated time to just hang out with our group at each stop. The bars we visited felt more upscale and local than the typical Broadway spots, which was a nice change of pace from the usual Nashville bar crawl. Highly recommend this one if you want something with a bit more character than the standard tourist route!
Operator response
Thanks so much for these comments! We aim to provide a unique experience of Nashville. Come back to see us!
Z
Highly reccommend
Thanks for a great tour. Great stories and education
Operator response
We appreciate you! Thanks for joining us.
A
Unforgettable Excursion with Drew!
If you are visiting Nashville, you absolutely have to book this experience. Our guide, Drew, was incredible—as a local, his knowledge of the city’s history was top-notch, and he took us to several hidden gems we never would have discovered on our own. Beyond the awesome sights, the dynamic of the group was fantastic. We were paired with people from all over the country and became fast friends, which made hanging out for the afternoon even better. It was an unforgettable excursion and the perfect start to our vacation!
Operator response
Thanks for these comments--it was great having you on the tour!
S
Absolutely loved our tour...
Absolutely loved our tour with Drew. He was great! Very engaging and knowledgable. Highly recommend!
Operator response
Thanks for the recommendation! We're so glad you joined us.
Compare similar tours in Nashville
| Tour | Duration | Rating | Price | |
|---|---|---|---|---|
| Nashville’s 1st Prohibition Cocktail Crawl: Secrets & Scandals | 2h 15min | 4.9 (41) | $48 | |
 Nashville's Wildest Honky Tonk Public Party Bus (21+) | 1h 45min | 4.9 (1,374) | $25 | View |
 Nashville to Jack Daniel's Distillery Bus Tour + Whiskey Tastings | 7 hours | 4.8 (1,979) | $140 | View |
 Grand Ole Opry House Guided Backstage Tour in Nashville | 1 hour | 4.7 (2,608) | $40 | View |
 Downtown Nashville Public Party Tractor 21+ Only | 1h 30min | 4.7 (2,739) | $25 | View |
 Grand Ole Opry Show Admission Ticket | 2h–2h 30min | 4.7 (2,734) | $62 | View |
 Best of Nashville City Sightseeing Tour on Double Decker Bus | 1 hour | 4.6 (2,937) | $35 | View |