Nashville Prohibition Cocktail Crawl: 4 Venues, Jazz-Era Tales

Walk four downtown venues and hear the true stories behind Nashville's Prohibition-era sin and scandals

Nashville's 1st Prohibition Cocktail Crawl is a two-hour guided walk through downtown's jazz-era nightlife, visiting four historic and hidden-gem bars with stories of bootleggers, corruption, and clever workarounds. A 5-star host leads small groups under a mile through the Men's Quarter, Smokey Row, and Printer's Alley, where the hooch flowed and the law looked the other way. Drinks are optional and à la carte at each stop.

Step-by-step itinerary

Explore Nashville's Prohibition-era nightlife

• Visit The Men’s Quarter
• Walk through Smokey Row
• See the Intersection of Sin & Salvation
• Explore Printer’s Alley

The experience

Two hours and under a mile of walking take you through downtown Nashville's most notorious Prohibition playground. Your guide leads small groups to four venues (a mix of historic bars, hidden gems, and era-inspired spots) each one a window into the bootleggers, corrupt cops, and high-rollers who kept the spirits flowing when the law said they shouldn't. The Men's Quarter, Smokey Row, and the intersection where church steeples cast shadows across gin joints set the stage for stories that are crazy but true.

Printer's Alley is the heart of it: by day a printing hub, by night a Prohibition playground where gangsters and politicians slipped past the law for bootleg whiskey and hot jazz. Today it still hums with speakeasy-style bars and sultry blues clubs. Your guide (a 5-star host and toastmaster) steers you through the shadows, the history, and the mischief, with time to snap photos in the glam and hidden nooks that made this strip legendary. Some venues may offer tour-only specials, though discounts aren't guaranteed everywhere.

Drinks are entirely optional and you buy only what you want at each stop. Drinking is not required to enjoy the crawl. The walk is relaxed and designed for groups, couples, bachelorettes, and anyone curious about cocktails paired with actual history. All areas and surfaces are wheelchair accessible, and public transportation options are nearby.

What’s included

• Stroll sin-soaked streets and hear shocking-but-true tales of bootleggers and corruption.
• discover four bootlegger-worthy venues with occasional tour-only specials.
• join a Jazz Age–steeped guide, toastmaster and ringleader.
• snap Instagram-worthy shots in hidden nooks and glam spots.

Information

Lasts 2h 15m, runs Thursday to Saturday at 16:00, from US$ 48 per person, with a live guide in English, in groups of up to 12 and with free cancellation up to 24 h before.

Days and timesThursday to SaturdayDeparts at 16:00Another day? ›

GroupUp to 12

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends at a different place from where it starts.

Book up to1h before

AgesAdult (21 and older) · Under 21: can't be booked

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated 2 days ago

Good to know

Low physical effortWheelchair accessibleAccessible transportStroller-friendlyPets welcomePublic transport nearbyNot recommended during pregnancy

Operated by Local Tastes of Nashville

Is this one for you?Small groups keep the energy intimate and the guide's stories close. The pay-as-you-go drinks mean you control what you spend and whether you drink at all, making it work for anyone curious about Prohibition history, whether or not they're a cocktail person.

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What is Printer's Alley and why does the tour spend time there?

Printer's Alley was Nashville's Prohibition playground: a daytime printing hub that transformed by night into a speakeasy strip where gangsters, politicians, and high-rollers bought bootleg whiskey and heard live jazz while the law looked the other way. Today it still houses speakeasy-style bars and blues clubs that keep its scandalous spirit alive, making it the centerpiece of the crawl's history.

How many stops does the tour visit and what kind of venues are they?

The crawl visits four downtown venues: a curated mix of historic bars, hidden gems, and era-inspired spots. They're chosen for their connection to Nashville's bootlegger past and their role in the city's jazz-age nightlife, not because they're all true speakeasies: Nashville doesn't have enough authentic speakeasies within walking distance to create a single route.

Do I have to drink alcohol on this crawl?

No. Drinks are optional and pay-as-you-go. You buy only what you want at each stop. Drinking is not required to enjoy the tour or the history.

What is the minimum age for this tour?

The minimum age is 21, since the crawl visits bars and alcohol is available at each venue.

How far do you walk and how long does the whole thing take?

The walk covers under a mile and the tour lasts two hours, making it relaxed and manageable for most fitness levels. The pace is designed to let you absorb the stories and the atmosphere of each venue without rushing.