SPEAKEASY SECRETS: The Original Roaring ’20s Cocktail Crawl
Overview
Available languages
2 hours
Mobile ticket
Explore the clandestine world of the 1920s with Nashville’s ORIGINAL Prohibition vintage cocktail crawl. Over two hours, visit four unique venues, from glamorous lounges to hidden hideaways, each serving authentic cocktails and sharing jaw-dropping true stories from the era. Your host will keep the energy high and the tales scandalous as you sip through this unforgettable experience. Perfect for bachelorettes, birthdays, couples, and history buffs, this tour puts a stylish spin on Nashville nightlife with an optional upgrade to a secret cigar lounge for the ultimate speakeasy finale.
● Discover four hidden bars with authentic 1920s cocktails
● Hear true Prohibition tales—no tourist-trap fluff
● Optional upgrade for access to an exclusive speakeasy cigar lounge
● Ideal for groups seeking a fun, stylish, one-of-a-kind night out
Additional Info
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.
What‘s Included
Stroll sin-soaked streets & hear shocking-but-true tales.
Join a Jazz Age–steeped guide: historian, toastmaster, ringleader!
Snap Insta-worthy shots in hidden nooks & glam spots.
Unlock “Gatsby Insider” discounts at our exclusive vintage venues.
Discover 4 hidden-gem, Prohibition-inspired bars & lounges.
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!
What To Expect
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.
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.
Options
The Original Prohibition Cocktail Crawl: Speakeasy Secrets!
Gold Key Experience VIP Upgrad
Exclusive Bonus Speakeasy Stop: Unlock access to a hidden speakeasy cigar lounge—underworld vibes, hush-hush cocktails, and a night you’ll never forget.
Duration: 40 minutes
Cocktails, Food, even Cigars!: Enjoy vintage craft cocktails, food, even cigars, if your interested. Pay as you go so you can enjoy things just your way!
Reviews
8 reviews
Total reviews and rating from Viator & Tripadvisor
Great story teller!
chicol608,
Nov 3, 2025
- Review from Tripadvisor
5.00Drew was a great story teller! Effortlessly spun the tales with flair, suspense and engaged the group. Drew also was very helpful in answering questions about where to find the best Blues in the city and other questions. Thanks Drew, highly recommend you!
Best experience ever!
K6952FWlh,
Oct 30, 2025
- Review from Tripadvisor
5.00Drew was not only extremely knowledgeable on the history of Nashville but he is a very talented story teller as well. We thoroughly enjoyed our experience. Thank you so much Drew! I will be back 😊
Fun experience!
Christin S,
Oct 26, 2025
- Review from Viator
5.00Drew was amazing! This was such a fun experience. Definitely recommend! We went to various bars that weren’t super busy but held so much information.
One of the best
M4889BUbrandonm,
Oct 24, 2025
- Review from Tripadvisor
5.00Drew was a great tour guide! We had so much fun on this tour and would highly recommend for anyone wanting to do something different but also enjoy some cocktails.
A fun night out in Nashville!
Rebeccavc75,
Oct 20, 2025
- Review from Tripadvisor
5.00Drew was a wonderful tour guide! He was very knowledgeable, and took us to some really fun spots. He got to know us, and tailored our trip to best reflect our interests. I would highly recommend booking a tour with Drew as your guide!!
Unexpected delightful experience we will treasure!!!!
Fred F,
Oct 18, 2025
- Review from Viator
5.00Dean was a wealth of experience and so full of energy. My son and I would never be able to see the hidden gems of Nashville night life. He made it a memorable experience and we will do it again. Also, we now can visit those hidden spots next time we are in town.
10/10
G2531HLjeffa,
Oct 13, 2025
- Review from Tripadvisor
5.00Drew was amazing! He had so much knowledge! He took us to so many fun places that we were always nervous to try and told great stories about them and their history. I can’t recommend this tour enough.
Speakeasy with Drew
alaynasmith31,
Oct 11, 2025
- Review from Tripadvisor
5.00Drew was an awesome tour guide! We learned so much Nashville history and went to some amazing places! Just when I thought the city couldn’t get more interesting and fun, Drew certainly delivered a fabulous time! Thanks so much
From $48.00
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Operated by Local Tastes of Nashville