Nashville: Prohibition Cocktail Crawl – Speakeasy Scandals

Nashville’s Prohibition Cocktail Crawl pairs a short downtown walk with stories of bootleggers, flappers, and the schemes that kept liquor flowing. The draw is as much the storytelling as the drinks: you visit four Prohibition-inspired venues, including at least one hidden speakeasy, but not every stop is a speakeasy.

I like two things about the format: the guide brings the era to life with true stories and vintage slang, and the route is easy to manage, covering about half a mile to one mile at a relaxed pace. One thing to weigh: the $44 price does not include drinks or food, and the venues are not all secret bars.

The essentials

• Four venues, one short route: Expect a two-hour downtown walk with stops in and around Printers Alley.
• A story-led crawl: Hear tales of Prohibition-era crime, bold women, unexpected enforcers, and the tricks used to keep spirits moving.
• At least one hidden speakeasy: The other venues take inspiration from the period, but may not be speakeasies.
• Drinks are pay-as-you-go: The $44 tour price covers the guide and hosted experience, not cocktails, wine, beer, or snacks.
• Dress-up is optional: Gatsby-era outfits make for fun photos, but curiosity is all you need.
• Plan for an easy walk: The route covers about 0.5 to 1 mile, with several stops along the way.

What this Nashville crawl is really about

This is not a race to sample as many drinks as possible. It is a guided night out built around the stories and style of Prohibition, with bars as the setting and cocktails as an optional extra. You move through downtown Nashville at an easy pace, pausing at four venues while your host supplies the history, local context, themed trivia, and a bit of Roaring ’20s attitude.

That distinction matters when you decide if the tour fits. If you want a list of famous bars and a drink included at every stop, this is not that. If you like a hosted evening that gives you a reason to look past the menu and notice a venue’s character, the format makes more sense.

The operator describes the stops as Prohibition-inspired, not all authentic speakeasies. At least one is a hidden speakeasy, while other bars are chosen for their vintage feel or their stories. One recent participant found that distinction disappointing at one stop, even though that venue had an interesting tale. Keep your expectations flexible: the crawl is about the period’s mood and history, not a promise that every door leads to a secret bar.

From 4th Avenue to Printers Alley

Most departures meet outside the Courtyard by Marriott at 170 4th Ave N. Look for a host wearing some Roaring ’20s flair. The 1:30 PM Sun’s Up, Bottoms Up edition meets outside Hotel Indigo / The Countrypolitan at 315 Union St instead, so check your departure details before heading over.

The tour ends at 8 4th Ave N, a short walk from the usual meeting point. The route covers about half a mile to one mile in total, with stretches of five to ten minutes between some stops. It is a manageable outing for most people who are comfortable walking, and the frequent pauses keep it from feeling like a march.

Your first stop is a downtown venue, where the group spends about 15 minutes. The menu may include cocktails, beer, wine, spirits, or local snacks, and there may be tastings or a photo opportunity. The exact offerings are not guaranteed, and purchases are separate from the tour price. Think of this opening stop as a chance to settle in, meet the group, and get the first layer of Prohibition-era context.

After a short walk, the group reaches Printers Alley for a roughly 25-minute stop. This is one of the route’s main story settings. The alley gives the crawl a fitting backdrop for tales of illicit liquor and the people who found ways around the law. You may choose a cocktail, but you can also take in the place and listen without ordering a drink.

The next downtown stop lasts about 30 minutes. It may offer another chance for a drink, a tasting, shopping, or photographs. Because venues can vary by day and group size, do not pin your plans on a specific bar or a particular tasting. The guide’s stories and the stop’s atmosphere are the reliable parts; the exact menu and venue can change.

A final short walk leads back to Printers Alley for the last 30-minute visit. At least one stop on the tour is a hidden speakeasy, and this is the kind of setting that gives the evening its secret-door appeal. The tour includes a guided visit and time to enjoy the venue, but it does not promise that every location will be a speakeasy. If that distinction matters to you, treat the crawl as a mix of themed bars and one concealed stop, rather than a tour of four secret clubs.

The route and stop lengths add up to about two hours. The host can keep the history moving while leaving room to pause, take photos, and enjoy a drink at your own pace.

The stories are the main event

The most consistently praised part of this crawl is the guiding. Drew and Dean have led recent tours, with visitors describing them as strong storytellers who make the history entertaining as well as informative. Those names are useful reference points, not a guarantee of who will lead your departure.

Expect stories about bootleggers, flappers, law enforcement, and the odd workarounds that helped liquor survive Prohibition. The tour also includes vintage slang, themed trivia, and group interaction. That mix should suit you if you enjoy history delivered with jokes and conversation rather than a long lecture.

One especially telling account came from a solo participant whose tour went ahead as a one-to-one experience after the guide offered the choice to cancel. That guest found the hidden bars and pop-up venues a useful way to see a side of Nashville they would not have found alone. The tour has a minimum of four people to operate, however, so do not assume you will get a private tour if bookings are light.

Drinks, food, and the real cost

The tour costs $44 per person, with all drinks and food paid for separately. That makes the final cost depend on what you order. You might enjoy the crawl with one cocktail, or decide to try something at several venues; either way, budget for purchases beyond the ticket.

For the price, you are paying for a two-hour guided walk, four venue visits, storytelling, trivia, and access to at least one hidden speakeasy. I see the value in that package if you want a host to connect the stops and give your evening a theme. It is less compelling if your priority is a drink-inclusive tasting, since no cocktail, beer, wine, or snack is bundled into the $44.

Non-drinkers can take part. The stories, trivia, photo stops, and settings are part of the experience, not just the drinks. You can skip alcohol and still follow the route with the group. Food and snacks are also optional and cost extra.

Who will enjoy the crawl most

This tour is a natural fit for a birthday, bachelorette outing, date night, or anyone who likes local history with a little theatrical flair. Costumes are welcome but not required. Gatsby-style clothing can add to the photos, but regular evening wear is fine as long as it follows the venue rules.

It also suits people who want a social introduction to downtown bars without having to plan every stop themselves. The host provides a route and a story, while the short distance leaves you time to linger. If you are already planning to visit Printers Alley, the crawl can add context to the area rather than simply sending you from bar to bar.

On the other hand, this is not the best choice if you want a quiet, formal history tour, a guaranteed lineup of speakeasies, or drinks included in the price. It is also limited to adults age 21 and older, and ID is required. The tour is wheelchair accessible, and it runs rain or shine, so come prepared for the weather.

Wear comfortable shoes, but note the dress rules: sandals, flip-flops, and sports shoes are not allowed. The stated guidance also rules out sleeveless shirts and ripped clothing. Bring a card or cash for any purchases, and leave large bags, luggage, strollers, and pets at home. Assistance dogs are allowed.

Should you book it?

Book the Nashville Prohibition Cocktail Crawl if you want a lively, story-led night out and are happy to pay separately for drinks. Its best value is the combination of a short, easy route, a host who makes history fun, and access to at least one concealed bar. Recent tours led by Drew and Dean have earned particular praise for their storytelling, though your guide may differ.

Skip it if the phrase speakeasy crawl means four secret bars to you, or if you expect the ticket to cover the cocktails. The venues can change, and one stop may be a themed bar rather than a speakeasy. Go in for the stories, the atmosphere, and the chance to find a spot you might not have picked on your own. That is where this crawl makes its case.

FAQ

How long is the tour?

It lasts about two hours.

How far will I walk?

The total walking distance is approximately 0.5 to 1 mile, at an easy pace.

Where does the tour meet?

Most departures meet outside the Courtyard by Marriott at 170 4th Ave N. The 1:30 PM Sun’s Up, Bottoms Up edition meets outside Hotel Indigo / The Countrypolitan at 315 Union St.

Where does the tour finish?

The tour finishes at 8 4th Ave N, Nashville, TN 37219.

Are drinks included in the $44 price?

No. Cocktails, beer, wine, and other drinks are optional and paid for separately. Food and snacks are also extra.

Does every stop count as a speakeasy?

No. The tour visits four Prohibition-inspired venues, and at least one is a hidden speakeasy. Not all of the venues are speakeasies.

Can I join if I do not drink alcohol?

Yes. Non-drinkers can take part in the storytelling, trivia, walking tour, and photo opportunities without ordering alcohol.

Do I have to wear a costume?

No. Gatsby-style clothing is optional. Comfortable shoes and weather-appropriate clothing are recommended, while sandals, flip-flops, and sports shoes are not allowed.

Is there a minimum age?

Yes. You must be at least 21, and ID is required. A copy of your ID is accepted.

Does the tour run in bad weather?

Yes. The tour runs rain or shine, so dress for the weather.