Nashville’s 1st Prohibition Cocktail Crawl: Secrets & Scandals

Nashville, US
100% of travellers recommend this
Excellent (49 reviews)
Self-guided

Included

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    Stroll sin-soaked streets & hear shocking-but-true tales.
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    Discover local venues with occasional tour-only specials.
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    Other
    Join a Jazz Age–steeped guide, toastmaster & ringleader!
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    Other
    Snap Insta-worthy shots in hidden nooks & glam spots.
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    Discover 4 bootlegger-worthy venues!

Excluded

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    Drinks & food – Pay as you go and ONLY buy what you want! Drinking is not required!
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    Gratuities
    Tips – Usual 20% (~$11.60) IF you have the fun we hope you do!

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!

Meeting point

170 4th Ave N, Nashville, TN 37219 , United States

End point

End Point

Final locations can vary but will be close to this intersection.

Meeting point

Nashville, TN , United States

End point

What to expect

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.

Duration 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.

Duration 30 minutes

The experience can be subject to change due to bad weather or unforseen circumstances. We always endeavour to give you the best possible experience.

Additional Information

  • Additional information
    All areas and surfaces are wheelchair accessible
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    Infants and small children can ride in a pram or stroller
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    Not recommended for pregnant travelers
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    Public transportation options are available nearby
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    Service animals allowed
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    Suitable for all physical fitness levels
  • Additional information
    Transportation options are wheelchair accessible
  • Additional information
    Wheelchair accessible
Provided by Local Tastes of Nashville

What our experts say

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    Arrive early for pre-tour cocktails
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    Check out nearby Pinewood Social for bites
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    Consider a visit to the Johnny Cash Museum
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    Dress stylishly to match the vibe
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    Bring cash for drinks and tips!

More About this Experience

Introduction

Step into the vibrant past with SPEAKEASY SECRETS! The Original Roaring ’20s Cocktail Crawl, where Nashville’s hidden history comes alive in the most exhilarating way. Over the course of two thrilling hours, participants will embark on a journey through four unique venues, each exuding the charm and elegance of the 1920s. The crawl isn’t just about cocktails; it's a sensory experience that immerses you in the stories and scandals of the Prohibition era. Accompanied by a spirited guide who doubles as a historian and entertainer, guests will sip on authentic vintage cocktails while learning jaw-dropping tales that echo through the streets of Nashville. This isn’t your average night out; it's a stylish adventure that captures the essence of a bygone era, perfect for those seeking a taste of history mixed with contemporary nightlife. Get ready to uncover the secrets of the city, one cocktail at a time.

What to expect?

When you join the SPEAKEASY SECRETS! cocktail crawl, expect a whirlwind of fun, history, and delightful drinks. As you navigate through four hidden gems, you'll discover not just the delectable flavors of expertly crafted cocktails, but also the captivating stories behind them. Each venue has its own unique ambiance, blending sophistication with a touch of the illicit charm that defined the 1920s. Guests will sip on drinks that are as rich in flavor as they are in history, while engaging with a knowledgeable guide who brings the past to life with every story shared. This tour is designed to keep the energy high and the laughter flowing, making it a perfect outing for bachelorettes, birthdays, couples, and history enthusiasts alike. And for those looking to elevate their experience, there’s an optional upgrade to a secret cigar lounge, adding an extra layer of luxury to your evening.

Who is this for?

SPEAKEASY SECRETS! The Original Roaring ’20s Cocktail Crawl is crafted for anyone who craves a unique and immersive night out. Whether you're a local looking to rediscover Nashville's vibrant nightlife or a visitor eager to explore hidden treasures, this tour is inclusive of all cocktail enthusiasts and history buffs alike. It's an ideal experience for groups—be it friends celebrating a special occasion, couples seeking a romantic adventure, or solo travelers wanting to meet new people in a lively environment. The tour is designed to be accessible and enjoyable for all, with wheelchair-friendly options and suitable for various fitness levels. So, whether you’re a seasoned cocktail connoisseur or just looking for a fun night out with a twist, this crawl welcomes everyone to indulge in the allure of the 1920s.

Why book this?

Booking the SPEAKEASY SECRETS! cocktail crawl means stepping into an unforgettable experience that beautifully intertwines history, culture, and nightlife. Unlike typical bar tours, this one promises authenticity, taking you to venues that are steeped in the rich lore of the Prohibition era. The engaging storytelling from your guide transforms each cocktail into a narrative, letting you savor not just the flavors but the history behind them. Plus, the option to access an exclusive cigar lounge elevates your evening to a true speakeasy experience, making it a perfect choice for those seeking something unique and upscale. So, why settle for a standard night out when you can immerse yourself in the captivating tales of yesteryear while sipping on expertly crafted cocktails? This is a chance to create lasting memories in a vibrant and enchanting setting that resonates with the spirit of the Roaring ’20s.

Good to know

Before joining the SPEAKEASY SECRETS! cocktail crawl, it's helpful to know a few things to enhance your experience. The tour meets outside a convenient downtown location, and it's suggested to arrive a bit early to enjoy pre-tour cocktails at exclusive “Gatsby Insider” pricing. While the tour is wheelchair accessible, it’s important to note that it may not be recommended for pregnant travelers. Guests should come prepared to pay for their drinks and food as they go, allowing for flexibility in what you choose to indulge in. The vibrant atmosphere is designed to accommodate all ages, but participants should be aware that drinking is not mandatory—enjoy the experience at your own pace. With the perfect blend of fun, history, and delightful libations, this cocktail crawl promises an evening you won’t soon forget.

Reviews

Those who have embarked on the SPEAKEASY SECRETS! cocktail crawl rave about the experience, noting how it effortlessly combines entertainment with historical depth. Guests have shared enthusiastic feedback about the knowledgeable guides, who bring the stories of the Prohibition era to life with wit and charisma. Many have highlighted the uniqueness of each venue, describing them as hidden treasures that added to the thrill of the night. Participants have particularly enjoyed the opportunity to try authentic cocktails that transport them back in time, while also relishing the chance to mingle with fellow adventurers. The optional cigar lounge has been a hit, with many expressing that it truly rounds off the experience in style. Overall, reviews reflect a profound satisfaction, with many saying this tour is a must-do when exploring Nashville's nightlife, creating cherished memories filled with laughter and history.

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