Nashville: Prohibition Cocktail Crawl – Speakeasy Scandals

Nashville’s Original Prohibition Cocktail Crawl turns a short walk through downtown into a lesson in bootlegging, bold flappers, crooked schemes, and the many ways people kept drinking when drinking was illegal. I like the true stories and crime tales, and I like that the route covers less than a mile at an easy pace. You are here for the stories as much as the drinks.

I also like the small-group feel, which gives guides such as Drew and Dean room to tell stories, answer questions, and keep the mood lively. The main catch is simple: the $44 price covers the guide and tour, but not your cocktails, beer, wine, or food. Your final cost depends on how much you order.

Key points to know before you book

• Four Prohibition-inspired venues: You visit a mix of cocktail bars and historic downtown stops, but not every venue is an actual speakeasy.
• At least one hidden speakeasy: The route includes a genuine secretive-style bar stop, though the exact locations can change.
• Drew and Dean lead the storytelling: Both guides bring humor, vintage slang, trivia, and strong knowledge of the period.
• Less than a mile on foot: The crawl moves at an easy pace through downtown Nashville and Printers Alley.
• Drinks are pay-as-you-go: The tour fee does not include cocktails, beer, wine, whiskey, champagne, or snacks.
• Costumes are optional: Gatsby-style clothing makes for fun photographs, but you can come in ordinary evening clothes.

A Roaring Twenties story walk through downtown Nashville

This is not a pub crawl where you simply move from one bar to the next. The drinks help set the mood, but the real subject is the strange machinery of Prohibition: bootleggers, secret rooms, bold women, unexpected enforcers, and the tricks used to keep alcohol flowing.

Your host acts as guide and emcee, mixing facts with vintage slang, toasts, themed trivia, and theatrical flair. Drew has been praised for turning history lessons into funny, easy-to-follow stories. Dean has also led a strong one-on-one version of the tour, adapting well when only one person had booked.

That flexibility matters. A small group gives you more chances to ask questions and hear the guide clearly. It also keeps the tour from feeling like a loud procession through downtown. The mood is social and playful, but the pace remains relaxed.

The crawl begins outside a downtown hotel, usually the Courtyard by Marriott at 170 4th Avenue North. Look for someone wearing noticeable Roaring Twenties flair and giving you a knowing look. The 1:30 p.m. Sun’s Up, Bottoms Up edition meets outside Hotel Indigo and The Countrypolitan at 315 Union Street, so check the start time and meeting place carefully.

Stop one: downtown drinks, photos, and the rules of forbidden fun

The opening downtown stop gives you time to settle in, meet the group, and get your bearings. Expect a photo opportunity, an aperitif or other drink option, and an early round of storytelling. Depending on the venue and the day, you may find beer, wine, cocktails, spirits, champagne, whiskey, or small food offerings available for purchase.

This first stop is useful because it sets the framework for the rest of the evening. You learn what Prohibition meant in practice, not just that the law banned alcohol. The guide explains the social schemes and workarounds that helped people continue drinking, then connects those ideas to the places you are visiting.

I would treat this as a good point to decide how much you want to drink. Since every beverage is extra, you do not need to order at every stop. Non-drinkers can still take part in the stories, trivia, photographs, and atmosphere without feeling pushed to buy alcohol.

The exact venue may change with the day or group size. That flexibility keeps the route practical, but it also means you should not book expecting one fixed list of bars.

Walking to Printers Alley without rushing

The first walk takes about five minutes. That sounds minor, but it shapes the whole experience. You are not covering a large section of Nashville or spending the evening marching between distant neighborhoods. The route stays compact in downtown, with a total walking distance of about half a mile to one mile.

Comfortable clothing and sensible footwear will help. The activity is wheelchair accessible, but the route still involves moving between venues and walking on downtown streets. Sandals and flip-flops are not allowed, and sports shoes are also listed among the restricted clothing items, so check the dress rules before you arrive.

Rain does not automatically cancel the crawl. It operates in wet weather as well as dry weather, so bring weather-appropriate clothing. A Gatsby hat or vintage-style outfit can make the photographs more fun, but dressing up is not required.

Printers Alley: cocktails and the first real taste of the theme

The next stop is in Printers Alley, where you spend about 25 minutes and can order a cocktail. This part of the route leans into the nightlife side of the story. The alley setting fits the era’s secretive mood, even though the tour makes clear that not every stop is a true speakeasy.

This distinction is important. The experience includes Prohibition-inspired venues rather than promising four original hidden bars. At least one stop is a hidden speakeasy, but other venues are chosen for their atmosphere, stories, or connection to the theme.

A cocktail here is optional. If you do order, bring a card or cash and remember that the drink is separate from the admission price. You might choose a classic-style drink to match the period, but the provided details do not promise a fixed cocktail menu, so do not book this expecting one specific recipe.

The short stop works best if you let the guide do the talking and resist treating it as a normal night out. You have plenty of time to enjoy a drink, but not enough time for a long meal or an extended stay at any one bar.

A second downtown stop with room for photos and local flavor

After another short walk of about ten minutes, the route returns to downtown for a longer stop of roughly 30 minutes. This section includes more time for photographs and a chance to browse or make purchases, depending on the venue. Beer, wine, and whiskey may be available, and the setting is chosen for its connection to the Prohibition mood.

This stop helps break up the evening. Instead of spending two straight hours in dark bars, you get a change of scene and a little more breathing room. If you are celebrating a birthday or planning a bachelorette outing, this is the sort of pause that can produce group photographs without forcing everyone to pose in the same place all night.

I also see value here for date nights. The crawl gives you built-in conversation topics, and the guide supplies enough structure that you do not need to plan every minute. The stories about bold women and creative lawbreakers give the experience more substance than a standard bar circuit.

The drawback is that shopping and food options are not guaranteed in a set form. They are listed as possible activities, not a fixed included part of the tour. Keep your expectations focused on the guide, the stories, and the bars.

A final Printers Alley stop and the hidden speakeasy element

The last major venue stop returns to Printers Alley and lasts about 30 minutes. This is the part most likely to satisfy anyone booking for the secret-bar angle. You receive more guided touring and sightseeing, with options that may include beer, cocktails, spirits, wine, champagne, and whiskey.

At least one hidden speakeasy is included somewhere on the route. The operator is careful to say that the venues are Prohibition-inspired and that not all of them are speakeasies. That wording is honest, and you should take it seriously. If your main goal is to visit four concealed cocktail rooms, this tour may disappoint.

If your goal is to understand the idea of a speakeasy while visiting a mix of atmospheric Nashville bars, the arrangement makes more sense. One stop can deliver the secret-door feeling, while the others add different stories and settings. One stop may not be a speakeasy at all, yet still offer an interesting story and a good drink.

This final section also gives the guide room to bring the themes together. You have heard about bootleggers, flappers, enforcers, and the public appetite for illegal liquor. The result is a portrait of Prohibition as a messy social battle, not a simple tale of good people versus bad ones.

What the $44 price really covers

At $44 per person, the price is reasonable if you want a guided history-and-nightlife experience rather than a package of drinks. You are paying for about two hours of live hosting, storytelling, venue access, group activities, and a route through four themed locations.

You are not paying for a tasting flight or a set number of cocktails. Drinks, food, snacks, and other purchases are extra. A light spender can keep the total close to the advertised price, while someone ordering at several stops will spend more.

That pay-as-you-go design has one clear benefit: you control your drinking and your budget. You can order a cocktail at the stops that interest you most, skip a round, or take part without drinking at all. For a non-drinker, that makes the activity more workable than a package built around mandatory alcohol tastings.

The value is strongest when you care about the host’s storytelling. The guides are the heart of the tour. Drew’s lively history lessons and Dean’s willingness to run a private-style outing show how much the experience depends on the person leading it.

Who will enjoy this crawl most

I would recommend it most for adults who want a social evening with a clear theme. It fits:

• Birthday celebrations and bachelorette groups
• Date nights with a built-in activity
• First-time Nashville visitors who want more than a standard bar stop
• People interested in American crime, nightlife, and Prohibition
• Solo participants who enjoy meeting a small group
• Non-drinkers who are happy to focus on stories and atmosphere
• Anyone who enjoys dressing up for photographs

It is less suitable for anyone under 21, since identification is required and the minimum age is 21. The activity is also not designed for people carrying luggage, large bags, strollers, or baby carriages.

The upper age guidance lists 95 as the limit. That seems unusually specific, but it is part of the stated suitability information. The most practical test is mobility and comfort with a short urban walking route.

How to prepare for the two hours

Bring a government-issued ID, or a copy if that is accepted for your booking. You will need proof of age, and you should not count on being served without it.

Wear comfortable, weather-appropriate clothing. Costumes are welcome, and Gatsby glam can make the photographs more entertaining, but you do not need a full costume to fit in. Avoid flip-flops, sandals, ripped clothing, sleeveless shirts, swimwear, see-through clothing, and other restricted items.

Leave luggage and large bags behind. Pets are not allowed, except for assistance dogs. The crawl runs rain or shine, so a light rain layer may be sensible when the forecast is uncertain.

You can cancel up to 24 hours ahead for a full refund, and a reserve-now, pay-later option is available. The tour needs at least four participants to operate, and the venues can change slightly based on the date and group size.

Should you book the Prohibition Cocktail Crawl?

Book it if you want funny, live storytelling paired with drinks and downtown nightlife. The strongest part is the guide-led interpretation of the era, especially with hosts such as Drew or Dean. The short route, small-group format, and optional drinking make it easy to fit into a Nashville evening.

Think twice if you expect four genuine speakeasies or included cocktails. You will visit four Prohibition-inspired venues, but at least one stop is not a speakeasy, and every drink is extra.

For a birthday, date night, or curious solo outing, I think the format offers solid value. You get a social activity, a bit of Nashville sightseeing, and a lively lesson in the bad behavior behind the Jazz Age. Just budget for your drinks, wear proper shoes, and arrive ready to listen as much as you are ready to raise a glass.

FAQ

How long does the Nashville Prohibition Cocktail Crawl last?

The experience lasts about two hours.

How far do you walk?

You walk approximately half a mile to one mile in total, at an easy pace through downtown Nashville and Printers Alley.

Are drinks included in the $44 price?

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

Are all four venues real speakeasies?

No. The venues are Prohibition-inspired, and the crawl includes access to at least one hidden speakeasy. Not every stop is a speakeasy.

What is the meeting point?

Most tours meet outside the Courtyard by Marriott at 170 4th Avenue North in downtown Nashville. The 1:30 p.m. Sun’s Up, Bottoms Up edition meets outside Hotel Indigo and The Countrypolitan at 315 Union Street.

Do I need to dress in Gatsby-style clothing?

No. Costumes and Gatsby attire are optional, though they are welcome and work well for photographs.

Is the tour available to people who do not drink alcohol?

Yes. Non-drinkers can take part in the stories, trivia, touring, photographs, and group activities without ordering alcohol.