Nashville: Prohibition Cocktail Crawl – Speakeasy Scandals

Secrets taste better after sunset. Nashville’s Original Prohibition Cocktail Crawl mixes vintage cocktails, tucked-away bars, and true stories about bootleggers, flappers, and crooked enforcers. I like the witty 1920s style of the guides, especially Drew’s lively storytelling and Dean’s willingness to run a private tour for one booked guest. The easy downtown route covers less than a mile, so you get plenty of time to listen, sip, and take photos.

I also like that drinks are optional and paid for as you go, which gives you control over the final bill. The main drawback is that not every stop is an actual speakeasy, despite the tour’s title. One of the four venues may be a Prohibition-inspired bar with an interesting story rather than a secret entrance or hidden room.

Key points to know before you go

• Four themed venues in about two hours: The crawl visits four Prohibition-inspired locations in central Nashville, with stops lasting roughly 15 to 30 minutes.
• At least one true speakeasy-style stop: The route includes access to at least one hidden speakeasy, but not every venue fits that label.
• Drinks cost extra: Cocktails, beer, wine, whiskey, champagne, food, and snacks are optional and purchased separately.
• Drew and Dean set the tone: Guide quality is a major part of the experience, with strong praise for their storytelling, humor, and command of Prohibition-era tales.
• Easy walking route: You walk roughly 0.5 to 1 mile through downtown Nashville, with short transfers between bars.
• Dress-up is optional: Gatsby clothing makes for good photos, but you can come in ordinary evening clothes.

Why this crawl feels different from ordinary bar-hopping

A standard Nashville night out often means loud music, packed bars, and moving quickly from one drink to the next. This experience takes a slower, more theatrical route. The host gives you a story before the next round, explains the slang and social rules of the 1920s, and turns each stop into part of a larger tale.

The focus is not only on what is in your glass. You hear about bootleggers, bold women, unexpected law enforcers, and the tricks that kept alcohol moving during Prohibition. That gives the evening a clear theme instead of making it feel like four unrelated bar visits.

I especially like the way the crawl uses history as entertainment without requiring you to be a serious history fan. You might learn about a crime, a loophole, or a clever business scheme, then raise a glass using vintage slang. The result is light and social, but there is enough substance to make the stops memorable.

The guides matter a great deal here. Drew receives especially strong praise for making history fun and easy to follow, while Dean earned praise for his knowledge and storytelling. The experience can also work well with a very small group. In one case, Dean offered to cancel because only one person had booked, but then happily continued with a one-to-one tour. That does not guarantee a private outing, but it shows a useful level of flexibility.

Meeting the guide at 170 4th Avenue North

For most departures, you meet outside the Courtyard by Marriott at 170 4th Ave N in downtown Nashville. Look for a guide wearing some Roaring Twenties flair and carrying the relaxed confidence of someone who knows where the city’s secrets are kept.

The 1:30 PM Sun’s Up, Bottoms Up edition uses a different meeting point, outside Hotel Indigo and The Countrypolitan at 315 Union St. Check your departure details carefully, since arriving at the wrong hotel could put you behind before the first story begins.

The tour begins and ends in the historic downtown area. That makes it easy to pair with dinner, shopping, or another evening plan, although you should leave room for the full two hours. The route is on foot, with transfers of about five to ten minutes between venues.

The walk is described as easy and totals roughly half a mile to one mile. Comfortable, weather-appropriate clothing matters because the tour runs rain or shine. Sandals, flip-flops, sports shoes, sleeveless shirts, ripped clothing, and several other clothing types are not allowed, so check the dress rules before you arrive.

The first downtown stop sets the Jazz Age mood

The opening downtown venue is used for introductions, photos, drinks, and the first round of stories. You may order an aperitif, beer, cocktail, wine, champagne, whiskey, or another spirit, but the drink is not part of the $44 booking price.

This first stop gives you time to meet the guide and the rest of the group before moving into the more focused storytelling. The host may bring in vintage slang, themed trivia, and a few period-style toasts. These touches help break the ice, especially for birthday groups, date nights, and bachelorette parties where not everyone knows one another.

The photo opportunities are part of the appeal. You can dress in Gatsby style if you want a full period look, but costumes are never required. A simple evening outfit works just as well, and the guide’s 1920s attitude supplies much of the atmosphere.

For non-drinkers, this is a useful feature of the tour. You can still take part in the stories, trivia, photos, and group humor without ordering alcohol. The crawl is built around drinks, but it is not limited to drinking.

Printers Alley brings the scandal closer

After a short walk of about five minutes, the group reaches Printers Alley for a cocktail stop lasting around 25 minutes. This part of downtown carries the strongest connection to Nashville’s after-dark character, and it suits stories about secret liquor, back-room deals, and people who learned to bend the rules.

The stop is less about rushing through a drink than giving the host room to explain what made Prohibition so strange. The guide may connect the cocktail in front of you with the social world that produced it, then add a story about a bootlegger, a daring woman, or an officer who did not always behave as expected.

The pace is one of the better features here. You are not asked to finish a drink and immediately move on. The crawl allows about 25 minutes at this stop, which is enough time to listen, order if you wish, and enjoy the setting without turning the evening into a race.

Drinks can add up quickly in downtown Nashville, so decide early how much you want to spend. Since each purchase is optional, you can order a cocktail at one stop, choose water or a nonalcoholic option at another, and still remain part of the group.

A second downtown venue may surprise you

The next walk takes about ten minutes and leads to another downtown stop. This visit lasts around 30 minutes and may include photos, beer, wine, whiskey, shopping, or more period storytelling.

This is also the point where expectations need a little adjustment. The crawl visits four venues inspired by Prohibition, but they are not all genuine speakeasies. One of the four stops may be an ordinary bar with a strong story rather than a secret venue.

That is not necessarily a weakness. A place can fit the theme through its history, design, drinks, or connection to downtown nightlife. Still, if you are booking mainly for secret doors and concealed rooms, you may find the format broader than the title suggests. One rating specifically dropped because a stop was not a speakeasy, even though the venue had an interesting story.

I would treat this stop as part of the historical tour rather than expecting a perfect movie version of the 1920s. The value comes from the guide’s explanation and the contrast between different settings. You may also find this a good moment for photos or a small purchase before the final venue.

The final Printers Alley stop provides the payoff

After another short walk of about five minutes, the group returns to Printers Alley for a final 30-minute visit. This is the most complete stop in the schedule, with sightseeing, guided history, cocktails, beer, wine, champagne, whiskey, and spirits all listed as possible options.

The final venue includes access to at least one hidden speakeasy during the experience. Because venues can change with the day and group size, the exact room or entrance is not fixed. That flexibility keeps the crawl practical for the operator, but it means you should not expect a guaranteed replica of a particular bar.

This last stop is a good place for the tour’s group energy to pay off. By now, you understand the guide’s humor and the period language, so the trivia and toasts feel less formal. You can take more photos, order another drink if you like, or simply enjoy the closing stories.

The tour ends at 8 4th Ave N, Nashville, TN 37219. You remain in central downtown, close to other evening options. Keep in mind that alcohol and walking can affect your pace, so do not plan a tight reservation immediately afterward.

What the $44 price really covers

At $44 per person, this is not a cheap way to drink in Nashville. The drinks are extra, and food or snacks are also excluded. If you order several cocktails at four venues, your total spending can rise well beyond the booking price.

The better way to judge the cost is to separate the guiding from the alcohol. Your fee pays for an expert host, guided touring, stories about Prohibition and true crime, access to four themed locations, at least one hidden speakeasy, group activities, trivia, and photo settings. You are paying for a two-hour event, not a package of included drinks.

I think the price works best for people who want structure and company. If you already know downtown Nashville and only want inexpensive drinks, you can spend less by choosing bars yourself. If you want a host to explain the city’s scandalous side and lead you to places you might not find on your own, the fee has a clearer purpose.

The pay-as-you-go system is also useful for mixed groups. One person can order a cocktail, another can choose beer, and a non-drinker can enjoy the stories without buying alcohol at every stop. Bring cash or a card for purchases.

Group size, guide style, and the human factor

This is a small-group experience, which matters in a bar setting. A large crowd can make it hard to hear a guide, gather around a table, or get everyone through a doorway. Smaller groups allow more room for questions and interaction.

The host is not just a person handing out directions. The role includes emcee, storyteller, history guide, and social organizer. Drew is praised for turning lessons into fun, while Dean is praised for strong storytelling and a deep command of the subject.

Those names are useful, but guide assignments can vary. You should book this for the format and theme rather than expecting one particular person. Still, the feedback suggests that the guide’s personality is a major strength of the experience.

The small-group format can also produce unusual outcomes. One booking became a one-to-one tour with Dean after only one person reserved a place. The normal operation requires at least four guests, so this should be viewed as an example of personal service, not a promise that every departure will run with one guest.

Who will enjoy it most

I would recommend this crawl to you if you like local stories, themed evenings, and a little theater with your drink. It works especially well for:

• Birthday celebrations
• Bachelorette groups
• Date nights
• Friends seeking a structured evening
• People curious about Prohibition and true crime
• Visitors who want more than the usual downtown bar list
• Non-drinkers who enjoy history and social activities

You do not need to own a flapper dress or a vintage suit. Gatsby clothing is welcome and photo-friendly, but ordinary evening clothes are fine as long as they meet the stated rules.

I would be more cautious if your main goal is a four-stop speakeasy tour. Not every venue is a speakeasy, and the locations may change according to the day and group size. I would also skip it if you dislike walking between bars or prefer a quiet tasting with little narration.

The event is for people age 21 and older, and you must bring identification. A copy of an ID is accepted according to the tour information. Unaccompanied minors are not allowed, and the activity is listed as unsuitable for people over 95.

Practical details that can make the night smoother

The crawl is wheelchair accessible, but it still involves walking between downtown venues. If you use a wheelchair, check the current route and venue access before booking, since the locations may vary.

Wear weather-appropriate clothing. The tour runs in rain or shine, and you will spend time outdoors between stops. Choose comfortable footwear that follows the dress rules, since sandals, flip-flops, and sports shoes are not permitted.

Large bags, luggage, baby strollers, pets other than assistance dogs, skateboards, skates, and other listed items are not allowed. Plan to arrive with only what you need for two hours, your identification, and a way to pay for optional drinks.

The tour is conducted in English. Free cancellation is available up to 24 hours before the start, and you can reserve now and pay later. Those policies are useful if your Nashville schedule is still shifting.

Should you book Nashville’s Prohibition Cocktail Crawl?

Book it if you want a social downtown evening shaped by stories, cocktails, and 1920s style. The best parts are the guides, the easy pace, the true crime and Prohibition tales, and the chance to visit venues you may not discover by simply walking into bars.

Go in with accurate expectations. You are not guaranteed four authentic speakeasies, and drinks are not included in the $44 price. But if you see the experience as a guided history crawl with optional alcohol, the value makes more sense.

For a first Nashville visit, a date night, or a celebration with friends, I think it is a strong choice. For a serious cocktail tasting or a strictly historical tour, you may want something more specialized. Bring curiosity, comfortable permitted footwear, and a little room in your budget for the glass you cannot resist.

FAQ

How long does the Prohibition Cocktail Crawl last?

The experience lasts about two hours.

How much walking is involved?

You walk approximately 0.5 to 1 mile in total at an easy pace, with transfers between venues taking about five to ten minutes.

Where does the tour usually meet?

Most departures meet outside the Courtyard by Marriott at 170 4th Ave N in downtown Nashville.

Is there a different meeting point for the 1:30 PM departure?

Yes. The 1:30 PM Sun’s Up, Bottoms Up edition meets outside Hotel Indigo and The Countrypolitan at 315 Union St.

Are drinks included in the $44 price?

No. Cocktails, beer, wine, whiskey, champagne, spirits, food, and snacks are optional and paid for separately.

Are all four venues actual speakeasies?

No. The venues are Prohibition-inspired, but not all of them are speakeasies. The experience includes access to at least one hidden speakeasy.

Do I have to wear a costume?

No. Gatsby attire and costumes are optional, although they are suitable for photos.

What age do I need to be?

You must be at least 21 years old and bring identification. A copy of an ID is accepted.

Is the crawl wheelchair accessible?

Yes, the experience is listed as wheelchair accessible, though it includes walking between downtown venues.

Can I cancel the booking?

Yes. You can cancel up to 24 hours in advance for a full refund. You can also reserve now and pay later.