Nashville: Prohibition Cocktail Crawl – Speakeasy Scandals

Nashville’s Original Prohibition Cocktail Crawl turns downtown into a two-hour stage of bootleggers, bold flappers, crooked schemes, and secret drinking spots. I like the way the tour treats the bars as part of the story, not just a row of places to order drinks. I also like the easy pace, with less than a mile of walking and small groups that give the host room to tell stories.

The guides are a major part of the experience. Drew is praised for his storytelling and fun history lessons, while Dean has led everything from group tours to a one-person crawl. The main catch is simple: the drinks are not included, and not all four stops are actual speakeasies. Some are Prohibition-inspired venues chosen for their atmosphere or story.

Key points to know before you book

• Four downtown stops in about two hours: You visit a mix of bars and Prohibition-inspired venues, with time to order drinks at your own pace.
• At least one genuine speakeasy stop: The crawl includes access to at least one hidden speakeasy, but the full route is not made up only of secret bars.
• Drew and Dean bring the stories to life: Expect true crime, bootleggers, flappers, vintage slang, trivia, and a host with a Roaring Twenties attitude.
• Less than a mile on foot: The route moves through downtown Nashville and Printers Alley at an easy pace, with walks of about five to ten minutes between stops.
• Plan to pay as you go: The $44 tour price covers the host, guiding, storytelling, and venue visits. Cocktails, beer, wine, food, and other purchases cost extra.
• Gatsby clothes are optional: Costumes make good pictures, but you can come in ordinary weather-appropriate clothing and still take part fully.

Nashville’s scandalous side, one cocktail at a time

This crawl works because Prohibition was never only about dry laws and dusty dates. It was also about workarounds, secret rooms, coded language, determined drinkers, and people who found ways to keep the party going.

You begin outside a downtown hotel, usually the Courtyard by Marriott at 170 4th Ave N. Look for the guide in distinctive Roaring Twenties clothing and carrying the air of someone who knows where the city’s secrets are buried. For the 1:30 PM Sun’s Up, Bottoms Up edition, the meeting point changes to Hotel Indigo and The Countrypolitan at 315 Union St, so check your departure time carefully.

The host acts as guide, emcee, storyteller, and timekeeper. That mix matters. You are not simply being led from one bar to the next. You are given a running explanation of the people and tricks that shaped the era, along with period slang, toasts, themed trivia, and plenty of chances to join in.

Drew receives especially strong praise for making history fun and educational. Dean has also shown a willingness to keep the tour going for a single booked participant, giving that person a one-to-one experience rather than canceling. You should not count on a private tour, but those names help you know what kind of personality may lead your group.

The opening downtown stop sets the mood

The first downtown venue is scheduled for about 15 minutes, though the exact place can vary. This opening stop combines a photo opportunity with the first drink or tasting choices. Depending on the venue and what you order, you might find cocktails, beer, wine, champagne, whiskey, spirits, or a small food tasting.

This short first stop is useful for getting your bearings. You meet the host, settle into the theme, and learn how the pay-as-you-go system works. Since drinks are optional, you can order a cocktail, choose another beverage, or take part without drinking alcohol.

The stop is also a chance to take pictures. Gatsby-style clothing is welcome, but not required. A jacket, flapper-inspired outfit, or other period touch can make the photographs more fun, though the experience does not depend on dressing up.

Do not expect a full meal here. Snacks and food are optional and not included, so eat beforehand if you need something substantial. The crawl is built around tastings and bar visits, not dinner.

Printers Alley brings the first proper cocktail stop

From the opening venue, you walk for about five minutes to Printers Alley. The second stop lasts around 25 minutes and centers on cocktails.

Printers Alley is a natural setting for this theme. The route uses the area as a place to connect Nashville’s present-day nightlife with stories of secret drinking and rule-bending. Your guide fills the walk and the stop with tales of bootleggers, unexpected enforcers, and the schemes that kept spirits moving during Prohibition.

This is one of the places where the experience feels most like a cocktail crawl rather than a standard city history walk. You can order a drink, listen to the story, and take in the setting without rushing to finish. The guide may also bring in vintage expressions and themed toasts to keep the mood playful.

Still, keep your expectations measured. The tour description is clear that not every venue is a speakeasy. If you are booking specifically to enter four secret bars, you may be disappointed. The route is better understood as a Prohibition-themed tour with drinks, including at least one speakeasy, rather than a strict survey of hidden cocktail rooms.

A longer downtown stop adds variety

After another walk of about ten minutes, the crawl returns to a downtown venue for roughly 30 minutes. This is the longest stop on the route and may include a photo stop, beer, wine, whiskey tasting, shopping, and more time to look around.

The extra time gives you a chance to slow down. A 30-minute stop is long enough to order something without feeling hurried, ask the host a question, and talk with the rest of your group. It also gives non-drinkers a better chance to enjoy the atmosphere without being pushed from one bar to another.

This stop may feel less secretive than the speakeasy portion. One person who joined the experience found one of the four stops disappointing because it was not a speakeasy, though the venue still had an interesting story. That is a fair warning. Each stop is selected for a vintage feel or a useful piece of the story, but the physical setting will not always match the secret-bar image suggested by the title.

I would treat the variety as a strength if you want a broader look at Nashville nightlife. If you only want concealed entrances and password-style drama, pay close attention to the wording before booking.

The final Printers Alley stop brings the crawl home

A short five-minute walk leads to the final Printers Alley venue. This stop lasts about 30 minutes and may include a guided visit, sightseeing, cocktails, beer, wine, champagne, whiskey, and other spirits.

The last stop is where the tour’s pieces come together. You have heard the stories, learned some vintage slang, seen several styles of venue, and had time to sample drinks at your own speed. The host can use the final stretch for more history, true crime, trivia, or a last round of themed banter.

The crawl finishes at 8 4th Ave N, Nashville. Because the start and finish are both in historic downtown, you do not need a separate ride between stops. You walk the entire route, with a total distance of about one-half to one mile.

That compact route is a real advantage. Downtown Nashville can be loud and crowded, but you are not spending the evening on a long march between far-flung neighborhoods. Comfortable shoes and weather-appropriate clothing are still important. The tour operates rain or shine.

What the $44 price really covers

At $44 per person, this is not a cheap night out if you also plan to buy several cocktails. The ticket covers the two-hour guided experience, the host, the storytelling, the themed group activities, and visits to four Prohibition-inspired venues. Drinks and food are separate.

The value depends on what you want. If you would otherwise spend the evening wandering from bar to bar without knowing which places fit the theme, the guided route can make the extra cost worthwhile. You are paying for access, structure, local stories, and a host who keeps the group connected.

The pay-as-you-go format is useful if your group has different budgets. One person can order a cocktail, another can choose beer or wine, and a non-drinker can join the stories without buying alcohol. It also prevents the ticket price from forcing you to pay for drinks you do not want.

On the other hand, you should set a spending limit before you start. A few cocktails can quickly cost more than the admission. Bring cash or a card, and remember that neither food nor snacks are included.

Why the small-group format matters

The crawl is designed for small groups, which suits a story-driven experience. A witty host can ask questions, run trivia, offer toasts, and adjust the pace more easily when the group is not large.

You will also have more room to hear the guide inside busy bars. This is important because the history is the main reason to book. The venues provide the setting, but the host provides the thread that links them together.

The experience can still operate with a very small turnout. Dean’s willingness to lead a one-person tour shows that the format can work privately, though the normal group size and exact arrangement may vary. A small group can be excellent for couples, friends, or solo visitors who want more interaction.

This is also a social activity without requiring you to arrive with a big party. Birthdays, bachelorette outings, date nights, and curious solo drinkers all fit the format. The guide supplies the conversation starters, so you do not need to plan the evening yourself.

Drinking is optional, not the whole point

The tour is built around cocktails, but you do not need to drink alcohol to enjoy it. Non-drinkers are explicitly welcome, and the storytelling, photo stops, trivia, and venue visits remain part of the experience.

That makes the crawl more flexible than a standard bar package. You can focus on the history, order a non-alcoholic option if available at the venue, or simply join the group while others taste drinks. Specific non-alcoholic beverages are not guaranteed, so ask at each stop if that matters to you.

For drinkers, the route offers plenty of choice. The scheduled stops may include vintage cocktails, beer, wine, champagne, whiskey, and spirits. The exact pours and venues can change based on the day and group size, so do not book expecting one fixed drink menu.

The guide’s role is to make the drinks part of the story. You may hear how vintage language, secret service, bootlegging, and social customs shaped the era. The best approach is to pace yourself. Four stops in two hours gives you time, but it is still a concentrated evening of bar visits.

Dress for pictures, but follow the practical rules

Gatsby attire is optional and photo-friendly. Dressing up can add fun to the pictures and help you feel part of the Roaring Twenties theme, but there is no need to buy a costume for this tour.

You should wear comfortable shoes and clothing suited to the weather. The published rules prohibit sandals and flip flops, sports shoes, sleeveless shirts, swimwear, ripped clothing, see-through clothing, and several other items. That is an unusually strict list, so check your outfit before you arrive.

Bring a government-issued ID or a copy. Everyone must be at least 21 years old, and ID is required. Unaccompanied minors cannot attend, and the experience is not suitable for anyone under 21.

The tour is listed as wheelchair accessible. Since the route takes place on foot and venues can vary, it is sensible to confirm current access details when booking, especially if your needs are specific.

Large bags, luggage, baby strollers, pets other than assistance dogs, skateboards, skates, and baby carriages are not allowed. Keep your belongings light so the walking and venue changes remain easy.

Who will enjoy this Nashville crawl most

I would recommend this experience to you if you like local stories with your drinks. It suits people who want more than a generic nightlife stop, but who also do not want a long lecture about Nashville history.

It is a strong choice for:

• Couples looking for a playful date night
• Birthday groups and bachelorette parties
• Friends who enjoy themed photos and cocktails
• Solo visitors who want a hosted evening
• Non-drinkers who like history, trivia, and lively settings
• Visitors who want to explore downtown and Printers Alley on foot

You may want to choose another activity if you dislike group entertainment, do not enjoy bar settings, or expect every stop to be a real speakeasy. The guide is central to the experience, so your enjoyment will also depend on how much you like storytelling, audience participation, and vintage humor.

Small details that make the evening easier

Book a departure time that fits your dinner plans. The tour does not include a meal, and the tasting portions or snacks available at stops should not be treated as dinner.

Arrive at the correct hotel meeting point. Most departures meet outside the Courtyard by Marriott at 170 4th Ave N, while the 1:30 PM edition meets outside Hotel Indigo and The Countrypolitan at 315 Union St. The guide wears recognizable Roaring Twenties flair, which helps you spot the group.

Allow extra time before the start if you need to find parking or make your way through downtown. The tour begins promptly from a central location, and you will be walking between venues.

You can cancel up to 24 hours before the experience for a full refund, and the reserve-now, pay-later option keeps your plans flexible. A minimum of four people is required for the tour to operate, so check the status of your chosen date.

Should you book the Prohibition Cocktail Crawl?

Book it if you want a compact, social Nashville night built around true stories, vintage style, and several different drinking spots. The strongest part is the guide-led storytelling, especially with hosts such as Drew and Dean, and the short walking route makes the evening easy to fit into a downtown visit.

Go in expecting four Prohibition-inspired venues, not four authentic speakeasies. At $44, the tour offers good value for its structure and entertainment, but you must add the cost of drinks. If that sounds fair, bring your ID, wear comfortable approved clothing, and let the city’s scandalous side take the lead.

FAQ

How long does the Prohibition Cocktail Crawl last?

The experience lasts about two hours, including visits to four Prohibition-inspired venues and walks between them.

How far do you walk?

The total walking distance is approximately one-half to one mile. The route includes walks of about five to ten minutes between stops and moves at an easy pace.

Are drinks included in the $44 price?

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

Do all four stops qualify as speakeasies?

No. The crawl includes access to at least one hidden speakeasy, but not all four locations are speakeasies. Some are Prohibition-inspired venues selected for their atmosphere or story.

Where does the tour meet?

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

Is dressing in Gatsby style required?

No. Costumes and Gatsby attire are optional. They are welcome for photographs, but you can attend in regular weather-appropriate clothing that follows the venue dress rules.

Who can attend the experience?

You must be at least 21 years old, and ID is required. The tour is wheelchair accessible, operates in English, and allows assistance dogs, but pets, unaccompanied minors, luggage, and large bags are not permitted.