Drunk History: Why a Cocktail Tour is the Best Way to Experience NYC Nightlife and History

Why a Cocktail Tour is the Best Way to Experience NYC Nightlife and History

Why a Cocktail Tour is the Best Way to Experience NYC Nightlife and History

New York City’s drinking history is nearly as ostentatious yet impressive as its skyscrapers. Representing nearly every culture in the world, there isn’t a drink you can’t get in the Big Apple. Want a delicate French wine with your meal? West Village. Looking for a shot of Ouzo that will put hair on your chest? Astoria. Looking for specialty crafted beer? Stumble into anyone's backyard in Brooklyn. Nothing pairs better with all that liquor than the stories that made them. New York's drinking history can be thought of like the drink tab of a Wall Street broker firm on a Tuesday night: long and expensive. 

This was one of the many reasons I was excited to take the Urban Adventures cocktail tour around the East Village on a cool June evening. There are drinking stories wherever you go in New York ( if you meet me on West 4th and 6th we can make one right now, wink wink), but the East Village was a hotbed during prohibition and is still on the forefront of drinking trends.

This was one of the many reasons I was excited to take the Urban Adventures cocktail tour around the East Village on a cool June evening. There are drinking stories wherever you go in New York ( if you meet me on West 4th and 6th we can make one right now, wink wink), but the East Village was a hotbed during prohibition and is still on the forefront of drinking trends. 

Urban Adventures stands out against other tours in the city for two main reasons: the local perspective and immersive history.

( If you thought I was going to say free booze and dranks, YOU sir are the one with a drinking problem).

Urban Adventures hires qualified locals to create their strolls around town, based on their interests and knowledge of their city. I always read history books before and during my travels because I have found that it is easy to just let the place wash over you when you are visiting.

When you walk through a place and understand the context behind it, it enriches your travels. And there is no better perspective than a local in my opinion. Every time I have had a local show me around- via couchsurfing, tours, or taxi rides- I have been able to fall in love and understand the place I’m in much more than if I was headfirst into a tour book the whole time. From a local perspective, you see how the city evolved, what they love and are frustrated by AND you find out where all the off the beaten path places are ( that’s why we are here, aren’t we ;) ). 

That is why I love what Urban Adventures is doing. They run hundreds of tours all over New York and the world. They have set up shop in over 90 countries and their tours are as diverse as their staff. Since it is a local showing you around, they handpick the best places for a visitor to experience. The groups tend to not overcrowd as well, so you can get chummy with your walking buddies and not fear being trampled on. Personally, as someone who is trying to make a career out of talking to strangers, I thought this was a perfect fit. 

I was especially excited to get a new perspective on my home town. As someone who walks miles over this city every day, I easily take for granted all the history and stories that have happened here (and the drinking that inspired it). All of the romances, murders, and pregnancies that have probably happened on one square block I’m standing on. Hopefully under the influence of alcohol. What am I not seeing? 

Because what usually drowns that forlorn thought out is one of the following.

  • Hordes of belligerent tourists dressed up as Santa/ leprechauns/ comic book characters who shout things like “it’s 5 o’clock somewhere!” or 

  • Avoiding getting hit by an UBER XL or

  • Surviving the mild claustrophobia and darkness of the subway or

  • Mentally strengthening myself for the swamp-like summer heat

...why do I live here again?

Nevertheless, I thought this cocktail tour around the East Village would finally give me a chance to slow down and appreciate a corner of the greatest city on earth (which is just the propaganda we are told so we don’t move to Westchester). If you are convinced by the end of this post to book Urban Adventures for your next trip, you can use my code STRANGERSABROAD for 10% off when you check out of their website!

Clink Your Glasses, Make Eye-contact, and Let’s Get Started

Clink Your Glasses, Make Eye-contact, and Let’s Get Started

We started the 3-hour tour at the corner of Tompkins Square Park, surrounded by people getting food stamps and barefoot hipsters walking poofy dogs with booties on. That is where I met Josh, our experienced tour guide, and an Aussie couple celebrating their birthdays. 

It was nice to have an intimate group, so I could avoid being shoved in the back of the tour and have to play a game of telephone with other visitors to hear what the guide was saying. 

Josh had a wonderfully upbeat attitude, not with the same droll demeanor that so many tour guides can have- or it might have been the fact that he knew we would be drinking soon- I don’t know. He started the tour by introducing us to the area and opened up a cardboard box filled with a modern NYC indulgence: cupcakes.

Prohibition Bakery 

Inside were six mini-cupcakes adorned with different creams and decorations. They were made by Prohibition Bakery where they create cupcakes based around iconic cocktails. You can have a round of Margaritas, Old Fashioned, or Mint Julep delivered right to your door ( if this was around in the 90s, Carrie Bradshaw would have maxed out her credit card here). Iconic New York in one bite. 

We each got two and tried to guess what flavors Josh got us.

I popped one in my mouth that was dotted with white frosting and a cute sprinkle of lime. Was it a tequila or gin? Maybe vodka with citrus? I am a notoriously terrible taster, so I buckled and believed my Aussie tour mates when they said it was tequila ( it was actually the Dark and Stormy). What did I learn from this? That Australian taste buds are too worn down to taste alcohol. They just recognize the burning sensation of liquor, and that it probably isn’t strong enough. Ok, I’ll let up. 

“Oh before we continue, does anyone have any allergies?” Josh asked. 

“Oh I have a gluten allergy,” I said with a mouthful of cupcake.  And a sugar addiction. 

They paused and stared at me, squinting their eyes. 

“It’s fine...I said...I think this one is a White Russian...?” as I polished off the second cupcake, trying to interrogate the cupcake instead of my eating habits.  

I avoid the side-eye of the Australian couple ( great first impression, Adrien!), and we started walking away from the park and towards our first destination. 

It was a sweet way to start the tour. Prohibition Bakery has created a perfect union between New York’s two biggest vices. 


We then moseyed over to Ladybird on East 7th Street ( which had been on my list of eats for a while). Ladybird is a small plates restaurant with pre-prohibition style cocktails. It’s not the kind of place to get sloshed, more like a place you want to bring your aunt to show that New York isn’t the deplorable place it used to be in the 70s. (Aunt Nancy, if you’re reading this: a lot has changed.) Typically a beautiful mint green arched door is the entryway to this new vegan bistro, but since it was June ( aka Pride month) it was evenly striped with every color of the rainbow.

We stepped in and felt like we were Daisy Gatsby’s apartment. It looks like the kind of place where someone could afford all of their Pinterest dreams. It was a dim-lit room with marbled walls and tabletops streaked with pink and gold. Chandeliers of crystal and baskets of tropical plants hung over the bar with a scintillating display case of liquor as couples relaxed on pincushion hightops. Large gold framed mirrors hang on the walls and reflected the rooms ostentation at you. 

We got ourselves a low lit booth in the back and had to squint to see the menu... even though there was still bright summer sun outside. Josh explained that we would be getting a punch here, which predated the cocktail. 

Before the years of illegal alcohol consumption and the rise of the cocktail, sailors used to mix their wine and beer that was spoiling over the their-this-is-never-going-to-end-mile journey with some kind of citrus juice and sugar ( so they could still drink to forget their crimes and avoid scurvy. Always the optimizers, those sailors). 

Josh ordered us the Reunion Ibis. It came in a large glass punch bowl, etched and spun with intricate decorations. It was the kind of vintage bowl that Downton Abbey would have served lemonade in for their guests on a hot summers day with cucumber sandwiches. Clinking ice against our glasses, we ladled the strawberry-basil-cucumber-riesling libation into our matching teacups ( which is what they would have drunk out of during Prohibition. When police officers would raid speakeasies, patrons could lie and say they were having “tea.” Not because they were broke college kids and only had mugs to drink out of). 

The Reunion Ibis was splendidly refreshing, and I happily helped myself to more when the Aussies tapped out early. We got a side of buffalo maitake buns to go with our punch, and as a healthy carnivore, I couldn’t believe I wasn’t eating meat. 

Ladybird was created by the DeRossi group which has its fingers in several New York City-based cocktail lounges and bars. They are reinventing how New Yorkers drink. Check out a number of their other themed cocktail bars like Mother of Pearl and Death & Co. 

William Barnacle- Absinth Lounge + Theater 

We then tipsily sauntered around the corner to St. Marks Place to the William Barnacle ( and no, that isn’t a Spongebob character). This unassuming, art deco absinth bar feels like it hasn’t been refurbished since its opening at the turn of the 20th century. It was filled with old decorations and knickknacks from the heyday of absinthe. 

We settled up around the bar and the eclectic clientele: young men with handlebar mustaches, older women covered in tattoos, and punk rock kids who seem to have just turned 21. Josh began explaining the history of absinth as our bartender laid out tiny glass cups and turned the spigot of an art deco absinth fountain that sculpted a woman as a stand. She is the alcoholic equivalent of Atlas, carrying the world’s drinking problems on her shoulders. The bartender poured a small amount of liquid into each dandy glass and placed a spoon along the rims and sugar cube on the spoon. As someone who lives in New York, I loved learning more about how my predecessors got lit. And by lit, I mean actually set their alcohol on fire. 

The way to make absinth (almost) taste nice is by lighting a sugar cup on top of the liquor and letting it drip down.


Setting the sugar on fire allows it to caramelize and drip down into the absinth pool below.

While our mild pyromania was occurring, Josh explained the war-torn history of this green liqueur. Absinthe was made illegal for many years across the globe and not for obvious reasons. The stories of people hallucinating and running amok were largely spun as a smear campaign during the 1800s by the French wine industry. They were threatened by how much faster you could get drunk on this booze ( to be fair absinth can be anywhere from 80-100% proof, so...wipes brow in worry). People might have only hallucinated because they were drinking it like wine. To be fair, even a small amount of absinthe will get you blitzed in a way wine never will. The worst thing wine will do to you is have you crawl into bed at an embarrassingly early time. Absinthe will have you jumping off a rooftop thinking you have embodied the spirit of the green fairy. 

The building itself has an eclectic past as well. Like all New York City buildings, it has to be resourceful of its limited space. Today, it is part prohibition bar, part theater with the Museum of the American Gangster on the second story. This is appropriately placed because some of the original NYC mobsters operated the bar below. 

The bar was owned and operated by a Bavarian gangster named Frank Hoffman during Prohibition. During this 13 year period ( which most folks thought would dry up as quickly as the counties did), roughly over 300,000 speakeasies were clandestinely open in New York City alone. This gave the Big Apple an alternative epitaph "City on a Still.” Prohibition was originally intended to decrease crime due to the Temperance movement, a political movement organized mainly by women who were tired of their husbands getting liquored up spending all of their money and beating them. But once Prohibition had become legal decreasing crime couldn’t have been further from reality. Crime spiked and this time was known as a graduate school for criminals. Mobsters would take petty criminals and turn them into gangsters. Most people believed that prohibition was going to be a cute little experiment not thinking it would last for as long as it did.

It might have been the only time where the rest of the world would say “ Drink up, there are thirsty children in America.”

Additionally, people were doing and drinking whatever they could to get blitzed. This was the genesis of bathtub gin and moonshine, made out of Tenement homes ( and in 2019 I STILL wouldn’t drink ANYTHING out of those bathrooms, no matter how well they are bleached).

It is good to note that during an economic depression or recession the consumption of alcohol has never gone down. Ever. As pious as the Temperance movement was, they clearly didn’t understand human psychology. 

Needless to say, thousands of businesses were disguised as some upstanding establishment, stashing the booze and toppers in the back. Which brings us back to the original operation of the William Barnacle, where Frank Hoffman masked the speakeasy as a butcher shop. When customers pretended to go in looking for Bratwurst but muttered the password to the butcher, he would lead them down a tunnel to the speakeasy ( it was probably easier than your onslaught of passwords: no need for 3 letters, 4 numbers, and one of $%#@&*!). He eventually left for Brazil with 12 mills on his, his bodyguard, and his girlfriend’s body and wound up dead a few weeks later ( although it is unsolved, rumor has it the bodyguard whacked ‘em both). 

Years later half of it gets repurposed into an off-broadway theater where an array of future celebrities worked from Frank Sinatra to Billy Crystal. The bar continues to serve shady characters and influences in the New York City political and financial sphere.

Where I was slurping down the refreshing strawberry punch from before, this drink was for the sipping, slowly, or faking sipping, slowly. I’m not a terribly heavy drinker, so even if they put 12 more flame-infused sugar cubes in this booze I still wouldn’t be able to knock it down and say that was pleasurable. I politely said thank you and left for our last destination with my glass half full. 

Warehouse Wine and Spirits

As that sugary punch and absinth began to settle happily together in my stomach, we took a quick pit stop at Warehouse Wine and Spirits, which easily has one of the most expansive and eclectic selections of alcohol in the city. We perused through these shiny metal bottles as our warped reflections stared back at us. They offer FREE delivery to anywhere in Manhattan on orders over $100 ( an easy task in this city, even if you have no friends). 

They also offer wine tasting at a makeshift bar at the center of the store. Already feeling loose, I naturally gravitated towards the free wine because...well it's free. Even with an upset stomach, I can’t say no to free. After ten minutes of testing, I was dragged away from having an emphatic conversation with the wine connoisseur and a man who promised that pressure points were the cure to jet lag...at the time it made a lot of sense. 

The Late Late 

Josh had us end our besotted evening at the Late Late ( no we weren’t so drunk that we kept forgetting what the name of the joint was). It is named after the longest-running show in Ireland and like its inspiration implies it had a solid whiskey selection. But like the Irish, they didn’t exclude themselves to just whiskey ( the Irish are fine knocking down anything that will get them drunk). The room was cozy and made with brick and wood walls, reminiscent of their homeland taverns.

By the end of the tour, I had easily forgotten to turn on my recorder, so this last section is based on my blurred and tipsy memory. Their cocktail list was playful. As a writer, I always appreciate a place that puts some effort into the titles of their homemade cocktails and was charmed by Sympathy for the Devil, Rocky Raccoon Martini, and Tiny Dancer. I parked myself at our table for one last drink. I got Friend of the Devil, not because I was feeling particularly impish, but because it was made with mescal, grapefruit, and blood orange. 

They had an expansive drunk food list, and we snacked on deep-fried cheddar cheese sticks ( because the Irish don’t eat mozzarella! Except for on their poor renditions of pizza it in Dublin which only taste good after the bars have closed and there is nothing left to eat). We spent the last few minutes recounting our personal favorite drinks and the best watering holes in NYC. If I remembered to write them down, I would have shared them with you. 

We spent our last few minutes together discussing our drinking phases and current obsessions. As I loudly slurped my last sip, I was sad it was over. I thanked Josh for a fantastic evening, and I sauntered ( probably stumbled) into the night, the feeling of being well taken care of lingered within me during my arduous train ride home ( and I know that wasn’t just the alcohol talking). But Josh, truly, gave us an interesting evening and more stories to recount than I could remember sober ( thank god for recorders). Although I am biases ( and was sauced up), I loved this tour and would recommend it to anyone who was overwhelmed with NYC drinking options and wanted an expert opinion on what to throw back ( local or visitor). 

What did we learn?

New Yorkers are desperate, yet adroit, alcoholics.

When you tell people not to drink, they drink MUCH more. 

Urban Adventures puts on a spectacular tour! If you want a discount for when you finally choose which tour you want to take ( trust me, you might need a drink to go through all of them!). When you are planning your next trip, you can use my discount code, STRANGERSABROAD, for 10% off of any tour IN ZE WORLD. Check them out when you are in New York City or any of your future travel destinations! Thank you so much Urban Adventures for the memorable evening :D

All pictures were taken from Squarespace website. They are not of the actual places mentioned ( sorry I don’t have a great camera! It’s on my to do list…)

Adrien Behn