Taking a Step Back in Time at BlackTail, New York's Cuban Prohibition-Era Bar

A photo wall featuring photos from prohibition era Cuba.
Take a step back in time to prohibition era Cuba in Sean Muldoon and Jack McGarry's new cocktail bar, BlackTail. Photos by Wendy Rose Gould.

Even as you approach the waterfront Pier Harbor house where NYC’s BlackTail bar is enclosed, something feels different. To your left you can make out a view of the green, glowing Statue of Liberty across the River Hudson’s inky waters, and you’re greeted by a gentleman at the door’s exterior who asks how many are in your party. Your answer somehow feels like a supreme secret to be told, and he buzzes the information up to the bar via an earpiece.

When the OK comes, the doors open and you’re met by a warm host who leads you inside the building, up a flight of glossy wooden stairs dimly illuminated by globular chandeliers, and into the bar itself. There – amidst clinking glasses, billowing green fronds and music that’s easy to sway to – is where the real magic of BlackTail hits you. Not only are you sent back in time to another era – the blind tiger days of Prohibition – you’re transported into a different land altogether: Havana, Cuba.

The interior of a bar with signs and photos from prohibition era Cuba. The decor and drinks of BlackTail bring you back in time to Prohibition era Cuba.

The bar

“The Cuban Prohibition-inspired bar was something that Sean had been planning and thinking about even before Dead Rabbit was realized,” says Jillian Vose, BlackTail’s beverage director. She’s talking about Sean Muldoon, of course, who co-founded world-famous Dead Rabbit with Jack McGarry. “It just took the right opportunity and the right space for it to happen.”

And they’re not kidding about the space. The name BlackTail references the fleet of swanky aircrafts that would transport thirsty, Prohibition-tortured Yankees to Cuba, where the alcohol ran free. Those black tails flew directly over the space where the Pier A Harbor house sits, so when the building became available, Muldoon and McGarry pounced.

The exterior of a bar in a two story building. Pier A Harbor house presented owners Sean Muldoon and Jack McGarry the perfect thematic location for BlackTail.

“We definitely wanted to have the same quality of drinks and experience as Dead Rabbit, but we wanted to make sure we paid homage to the timeframe that we were aiming for – America’s prohibition era in Cuba,” she says. “The area in which we’re located, the storyline of the menu, and the timeline of the drinks … it had to make sense. It all had to be relevant.”

The house rum

From the ambiance to the servers’ garb to the menu and (most importantly) the drinks, every single facet of BlackTail has been painstakingly perfected. Take their rum blend, for example, which combines nearly 30 different rums from four brands to create an authentic, Cuban-style rum that’s fresh, dry and versatile. It’s a key ingredient in many of their drinks, and it makes for one of the most delicious rum and Cokes you’ll ever have the pleasure of sipping.

“We really wanted to make our own house-style rum that paid homage to Cuban rum,” Vose tells us. “The two rums on the market that are closest to what you’d get to Cuban rum are Bacardi Heritage and Caña Brava by The 86 Co., so we decided we’d blend those two together.”

To that, they added Vose’s own personalized rum blend, which includes Barbancourt’s fruity, banana-leaning White Rhum and Banks Five Island, which is actually already a blend of about 25 unique rums.

“We probably created the blend – I don’t know – 500 times until we got the perfect rum blend that worked with all our different daiquiris and drinks,” she says.

A cocktail menu book next to a cocktail. BlackTail's menu encompasses its versatile drink offerings divided into five categories (highball, punch, sour, old fashioned and cocktail), as well as a small novel in the back of its hardcover presentation.

The menu and drinks

Speaking of daiquiris, BlackTail has four on the menu – classic, strawberry, banana and pineapple – and you’re given a sample of one as soon as you’re seated and another before you depart.

“Maybe back in the day when we all started bartending, a drink like the daiquiri would be considered way amateur. When you think about them, you imagine a generic slushy coming out of a machine,” she says. “But we wanted to make a really nice version that was true to Cuban style, and we found that with today’s technology and using different techniques for syrups – such as the sous-vide method that brings out a brighter, fresher flavor – we were able to come up with something really authentic and complex.”

A bar with cocktail syrups. To create housemade syrups with delicate, elevated and complex flavors, the team at BlackTail sous-vides the ingredients.

In addition to using the sous-vide method for all their syrups, BlackTail also applies the same technique when infusing their rums. Take their Old Fashioned Saratoga, for example, which combines a pineapple infused rum with cognac, Irish whiskey, curacao, almond, apple, caramel and cherry.

That same attention to detail and utilization of flavor-enhancing techniques is the approach BlackTail takes to its entire menu of drinks. The book itself – and it is an actual hardcover book, complete with a mini novel in the back – divides the drinks into five categories: highball, punch, sour, old fashioned and cocktail.

“When we were doing the menu, we mapped everything out so that each section featured a particular glass with a particular ice to make for simple navigation,” says Vose, who added that much research went into the glassware so that it, too, was authentic and true to the drink style.

Dividing the menu this way makes it a little easier to narrow down your drink choices, but you can rest assured that any glass delivered to your table will elicit lifted eyebrows and a satisfied palate. Even drinks as simple as BlackTail’s champagne and amaro-spiked Rum & Cola, or the Southside, a Cuban Prohibition era riff on your modern day mojito, are elevated and a little extraordinary.

Other classics include their Pineapple Milk, which tastes like a creamier, vanilla version of a traditional piña colada, and the Mary Pickford, a bright and fruity punch that combines cherry, pomegranate, pineapple, lime and burlesque bitters with their house Cuban rum blend.

Those are just a few examples of menu offerings, all of which can be held in your own hands simply by stepping out of your current reality and into the world that BlackTail has so carefully crafted.

Wendy Rose Gould is a freelance lifestyle reporter and photographer based in Phoenix, Arizona. From Tel Aviv to Miami, from Prague to NYC, she enjoys sipping on well-crafted cocktails in all corners of the world.

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