Speakeasy Drinks and Prohibition History Tour NYC

New York’s Prohibition story comes alive here through three very different bars, not a museum display. You walk from 8th Avenue through Times Square, Broadway, and Midtown, hearing about the city’s old drinking culture before settling in for cocktails you buy along the way.

I like the small-group setup, with no more than 18 people, and the guides often make the night. Ryan is praised for his storytelling and humor, while Ariel, Walter, Katherine, Kathryn, Julian, Emma, and D have each led lively tours. The main catch is that not every stop feels like a true speakeasy, and three cocktails can cost more than the $38 tour fee.

Key points at a glance

• Three bars, three moods: Expect a mix of historic-feeling rooms, modern cocktail bars, art deco style, live music, and places that feel more like regular nightlife.
• Strong guide element: Ryan, Ariel, Walter, Katherine, Kathryn, Julian, Emma, and D are among the guides named by past customers for humor, history, and good pacing.
• Drinks cost extra: Admission is included, but cocktails are not. Plan on roughly $20 per drink at each stop, plus any required tax or gratuity.
• Midtown walking route: The tour starts at 825 8th Avenue and ends around Times Square, passing Broadway and central Midtown landmarks.
• Dress matters: Wear upscale casual clothes. Sportswear and ripped clothing are not allowed.
• Best for adults: You must be at least 21 and carry valid photo ID. Non-U.S. citizens need a passport.

What the $38 tour actually gives you

The base price is modest for a three-hour New York night out. For $38, you get a guide, the walk between venues, admission at all three places, and preferred entry. You do not get food or drinks, and that changes the final bill.

Cocktails often run about $20 each, according to the practical details shared after the tour. Three drinks can therefore add around $60 per person before any extra spending. For two people, the drinks alone may reach $120, putting the evening well above the headline tour price.

That does not make the tour poor value. It means you should compare it with a guided night out, not with a simple walking tour. You are paying for access, company, route planning, and stories, then paying separately for the bar experience.

I like that you can choose your own drinks rather than being locked into a package. You can keep the cost down by ordering less, but the tour is clearly designed around having at least one drink at each stop. If you are not interested in cocktails, this may not be the right use of your evening.

Starting on 8th Avenue and entering Midtown nightlife

The meeting point is 825 8th Avenue, New York, NY 10019. From there, the guide sets the tone with stories about Prohibition and New York’s Gilded Age, then leads the group toward the first venue.

The route is centered on Midtown. You pass through Times Square, the Broadway theater district, and an area just north of Times Square and south of Central Park. One part of the walk also reaches a historic, culture-focused neighborhood, though the exact streets and bars can vary.

This is not a long-distance hike. One person who took the tour described the amount of walking as manageable for a three-hour experience. Still, you should wear shoes that are comfortable on city pavement. You will be moving between venues, waiting for entry, standing at bars, and spending part of the night indoors.

Times Square is a useful setting for this theme because the modern streets hide the older nightlife story. The route lets you see a very public entertainment district while hearing about a period when drinking often had to stay out of public view.

The first bar usually delivers the strongest speakeasy mood

The first stop appears to be the most convincing match for the classic idea of a speakeasy. Details shared about one visit included an unmarked entrance, a password, and creative cocktails. That gives you the small thrill the name promises, especially if you enjoy places that make entry part of the experience.

The first venue may also be where the guide can set up the night’s main ideas most clearly. You are not simply being taken to a bar. You are hearing how secrecy, alcohol, nightlife, and New York personalities shaped one another during Prohibition.

Music volume can affect the experience. At some visits, loud sound made it harder to catch the guide’s stories at the first or final stop. If you have trouble hearing, move close to the guide before the storytelling begins, rather than staying at the far edge of the group.

The drinks are part of the fun, but they are not included. You order and pay separately, so ask the guide how the bill will be handled before ordering if you want to track the cost carefully.

Times Square and Broadway connect the bars

The walk between stops is not filler. It gives the guide room to connect the venues with the city around you. Times Square can feel loud and commercial today, while Broadway adds the long-running theater side of Midtown nightlife.

The exact route is less important than the contrast. You begin with a guided story about an earlier New York, then walk through streets packed with modern signs, theaters, restaurants, and bars. That contrast helps explain why the city’s drinking history is best understood on foot.

Your guide is a major part of this section. Ryan is repeatedly praised for telling stories with humor and keeping the group involved. Ariel, Walter, Katherine, Kathryn, Julian, Emma, and D are also named as engaging guides. Their styles will differ, but the tour depends heavily on having someone who can hold a group’s attention outdoors and in noisy rooms.

The group limit of 18 is helpful. It is large enough to create a social evening, but small enough that you should be able to hear the guide more easily than on a big bus or crowded city tour. A solo visitor may find the group especially useful, since the three-hour format gives you an easy way to spend an evening with other adults.

The second and third stops may be modern bars

This is where you should set your expectations carefully. The three venues range from modern to historic, and not every room has a hidden door or a genuine Prohibition setting.

One stop has been described as Lillies, a clearly marked restaurant rather than a secret bar. Another has been described as a newer art deco-style venue with a polished, upscale feel. These places may serve good drinks and offer attractive interiors, but they do not necessarily feel like places that survived from the 1920s.

That distinction matters. If you want three authentic, hard-to-find speakeasies, the tour may disappoint. If you want three different cocktail settings linked by a guide’s stories, the changing styles are a strength.

The venues can also change, and individual nights may feel different. Themes mentioned across the experience include an 80s sexual-freedom setting, a dark Broadway mood, and a place with live music. This variety keeps the evening from becoming repetitive, but it also means the Prohibition link may be stronger at one stop than another.

The final bar may offer food, but food is not part of the tour price. One account praised the food while finding the drinks less appealing, so treat the final stop as a chance to choose for yourself rather than assuming every cocktail will be a winner.

The stories matter more than the secret doors

The best reason to book this experience is the guide-led storytelling. The bars provide the setting, but the guide supplies the meaning.

You can visit trendy Midtown cocktail bars on your own. You cannot easily recreate the route, the historical framing, and the introduction to three venues in one evening. Guides such as Ryan and Walter are praised for making the history easy to follow, while Ariel and Katherine are noted for mixing information with humor and personal New York perspective.

The strongest guides also adjust to the night. One account describes a guide changing plans as conditions shifted and remaining patient. That matters in New York, where weather, music levels, door policies, and crowd size can affect the pace.

Still, this is not a quiet history lecture. You will hear stories while standing in active bars, and the music may be loud. If you want detailed historical instruction at every stop, ask questions during the quieter walking sections and stay near the guide.

What to wear and bring

The dress code is upscale casual. Sportswear and ripped clothing are not permitted, so leave athletic clothes and torn jeans behind. You do not need formal evening wear, but neat city clothes are the safer choice.

Bring valid photo identification. The minimum age is 21, and non-U.S. citizens need a passport. This is not a detail to leave at the hotel, since the venues serve alcohol and the tour may require ID checks.

Use public transportation to reach the start if that suits your plans. The meeting point is near transit, and the tour ends in Times Square, a convenient place for continuing your evening or returning to your accommodation.

The experience is offered in English. You should also expect a moderate amount of walking and standing, even though the route is not described as strenuous.

Is the three-hour length right for you?

Three hours sounds long for three bars, but the time includes walking, venue entry, storytelling, ordering, and conversation. Several people found the length comfortable, and one person who worried that three hours might drag found that it did not.

The pace works best if you enjoy settling into each stop rather than rushing in for a quick drink. You get time to notice how the venues differ and to talk with the guide and the rest of the group.

The length may feel less useful if you are mainly after a secret entrance and one memorable cocktail. In that case, the first stop may deliver what you want, while the later venues may feel like ordinary nightlife with a historical introduction.

Start times are available at several points in the day, which makes it easier to fit the tour around a Broadway show, dinner, or sightseeing schedule. Check your chosen time carefully, since the route is built around an evening-style bar visit.

Who will enjoy this New York night out?

I would recommend the tour to couples, friends, solo adults, and families with members who are all at least 21. It is a social experience, and the small group gives you a good chance to talk with others without being placed in a huge crowd.

It suits you especially well if you like:

• New York history told through people and places
• Creative cocktails and polished bar rooms
• A guided night activity rather than a formal museum visit
• Walking through Midtown after dark
• Meeting other adults while sightseeing
• Guides who use humor and personal stories

I would hesitate if your main goal is historical accuracy at every venue or three genuine old speakeasies. The first bar may feel secret and atmospheric, but the second and third stops can be plainly visible, modern, or more restaurant-like.

The tour also requires a reasonable drink budget. At $38, admission is fair, but three $20 cocktails can turn a low-cost booking into an expensive night. You can ask about prices before ordering and control your spending, but the extra cost is part of the experience.

Booking, cancellation, and final advice

The experience is often booked about 29 days ahead, so popular dates may fill before your trip. Confirmation arrives at booking, and the group size is capped at 18.

Free cancellation is available up to 24 hours before the start time. Changes made within 24 hours are not accepted, and late cancellations are not refunded. If the minimum number of people is not reached and the tour is canceled, you are offered another date or experience, or a full refund.

So, should you book it? Yes, if you want a social cocktail walk with Prohibition stories and you are comfortable paying separately for drinks. The guides are the strongest part, and the first venue may give you the classic secret-bar feeling.

Skip it if you want a strict history tour or three untouched speakeasies. Go in expecting a mix of historic ideas, modern bar culture, and Midtown sightseeing, and the $38 fee makes better sense.

FAQ

How much does the tour cost?

The tour costs $38 per person. Drinks and food are not included.

How long does the experience last?

The tour lasts approximately three hours.

How many bars will I visit?

You will visit three bars or speakeasy-style venues.

Are drinks included?

No. You purchase your own cocktails and drinks at each venue.

How much should I budget for drinks?

Cocktails may cost around $20 each, based on details shared about the experience. Three drinks can add about $60 per person before any additional spending.

Where does the tour start?

It starts at 825 8th Avenue, New York, NY 10019.

Where does the tour end?

It ends around Times Square in Manhattan, New York, NY 10036.

What is the minimum age?

The minimum age is 21. You must carry valid photo identification, and non-U.S. citizens need a passport.

What should I wear?

The dress code is upscale casual. Sportswear and ripped clothing are not permitted.

Can I cancel for a refund?

Yes. You can cancel at least 24 hours before the start time for a full refund. Cancellations or changes made within 24 hours are not refunded or accepted.