A Night Out With Holiday Vodka

Martinis, caviar service and bopping around town with founder Anna Goldman, a newcomer to the spirits space who wants you to have a favorite vodka

July 7, 2026 2:56 pm EDT
a man's hand scooping caviar into a small bowl next to a silver ice bucket with a bottle of holiday vodka
Caviar service? Yes, please.
Amanda Gabriele

Single New York guys, take note: All of the cool, interesting women are drinking at Elvis, a petite, Parisian-inspired wine bar on Great Jones, “an iconic block” if there ever was one, according to owner Darin Rubell. “Guys don’t go out like this, to grab a glass of wine and snacks,” he says.

We are, indeed, surrounded by tables of women, chatting, drinking and snacking on perfectly prepared small plates like hamachi crudo, charcuterie and tiny bowls of radishes and butter. I myself am having a girls night, in the company of Holiday Vodka founder Anna Goldman, her COO Olivia Peniston and Holiday publicist Tanner Tompkins. While, yes, Elvis is a wine bar, we’ve opted for cocktails — Anna and Tanner are sipping Espresso Martinis, while Olivia and I are drinking the Jones Collins, a tall refresher with vodka, pastis, dry vermouth, lemon and sparkling water. All of them, of course, are made with Holiday, a spirit we’ve asked for by name. 

A Holiday Vodka Espresso Martini; the scene at Elvis
A Holiday Vodka Espresso Martini; the scene at Elvis
Amanda Gabriele

“In the vodka space, there wasn’t necessarily a brand that people felt loyal to the way they felt with whiskeys, gins and tequilas,” Anna says as Darin sits down with us for a chat. “I started talking with bartenders and other beverage directors to ask, ‘Is this a trend?’ And they told me when people order vodka, they either order Tito’s or it’s the bartender’s choice. So I saw an opportunity to create something people are excited about, the way they are with their whiskeys, gins and tequilas.”

There is, indeed, a lot of excitement around Holiday. Though it’s only been around for a year, it’s already on the backbar of downtown Manhattan’s most popular destinations — The Corner Store, Pearl Box, Jean’s and Zero Bond, to name a few. The crowds out East will certainly be seeing it this summer in venues like Gurney’s, Surf Lodge and Sunset Beach on Shelter Island, the latter of which has a very special place in Anna’s heart.

“I’ve been going there as long as I can remember,” Anna says. “I went to them and said, ‘Nothing would make me happier or prouder than to have Holiday here.’” Now it’s one of the best-sellers at Sunset Beach. 

We finish our cocktails, and by 6 p.m. are in a cab to the next place, Pearl Box. We’re greeted at the door by Kenneth Crum, managing partner of Pearl Box and one of the coolest somms I know. He takes us up the mirrored staircase to the third-floor bar, dubbed The Attic, where warm wood, ruby-red carpet and chrome-lipped tables evoke a sultry, ‘70s vibe. Each table is topped with a menu inspired by vintage Playboy magazines, the centerfold being the cocktail of the moment. “People don’t think of this, but Playboy was very fashion — not at all what it is today,” Kenneth says as he leads us to our table.

a box of candy and martini on a pearlbox menu and a bartender making cocktails
Candy and cocktails at Pearl Box
Amanda Gabriele

It’s a Wednesday evening, and the bar is bustling. Outside, people gather around sidewalk tables to take in the perfect summer weather. Up here, tables of friends and couples on dates are sipping Champagne and cocktails. I go for the Après Italiano, a mix of Holiday Vodka, Heirloom Crème de Flora, Chiot Montamaro, orange and cinnamon. Yes, it was designed as a winter drink, but I’m here for the full Holiday Vodka experience. 

“Our launch party was a holiday party in December,” Anna says. “Holiday was concepted to be this European summer getaway brand, but what’s so fun about the world ‘holiday’ is that it really evolves throughout the seasons. Olivia and I especially love the winter holiday.”

“We love to ski!” Olivia adds. “We basically turned St. Theo’s into a ski chalet. We took out every single framed photo they had and replaced it with a custom photo [that Olivia herself designed]. It was the best day ever.”

Anna Goldman and olivia Peniston of Holiday vodka
Anna Goldman and Olivia Peniston of Holiday vodka
Amanda Gabriele

It’s clear that Anna and Olivia have a simpatico relationship — it seems like they’ve known each other forever. As our server brings over plates of chili crisp cucumber salad, shrimp cocktail and five-spiced popcorn chicken, I get the scoop on how they met. 

Anna: “I hadn’t hired anyone yet because we didn’t have any revenue. But then my husband’s chief of staff told me, ‘My brother’s girlfriend is graduating from Stanford business school, and I think you should meet. She’s in town for like three hours.’ So I met Olivia at the coffee shop across the street from my apartment.”

Olivia: “It was jam-packed. So we went for a walk around Central Park.” 

Anna: And I loved Olivia immediately. She was going back to California, so I said, ‘This could sound a little weird, but before you go, do you want to come to my apartment?’ It’s like 10 a.m., mind you.” 

Olivia: “I told her, respectfully, I will never work on anything that I don’t truly love and believe in. So I went to Anna’s apartment to actually try Holiday, and, yes, it was like 11 in the morning. We had neat Martinis. If you can even count that as a Martini.

Anna: It was neat vodka. We had vodka.

Olivia: So I tried Holiday and I was like, wow, this is fantastic. I know there’s something here. So I basically said, ‘Let’s do it.’” 

How High-Volume Bars Make Hundreds of Complicated Cocktails During Service
Nine bartenders discuss how they keep things consistent and high quality, even when the place is packed

“Choo-choo!” Kenneth says as he rolls Pearl Box’s caviar cart over to our table. “Everything you’re eating could use a little caviar, so I brought you caviar.” Claps and expressions of delight are had ‘round the table as we scoop the umami-rich fish roe onto crispy nuggets of fried chicken. Pearl Box launched their own caviar line a couple of years ago, and it’s been a hit at everything from award shows to Knicks games at MSG. 

“We had Martinis, caviar and candy at the Emmys,” Kenneth says while we dig in. 

“Do you need anything else?” Anna replies. “Maybe French fries.”

I can’t leave Pearl Box before having one of their Martinis. I opt for the Filthy, a mix of Holiday Vodka, Ms. Pearl’s brine blend and Castelvetrano olive. It’s perfect in every way, as is the Classic, which Olivia lets me try. That one combines vodka, lemon oil and Mancino Secco vermouth, the latter of which is the same producer of Holiday. 

A lot of people are afraid of vermouth, likely because they tried one that was oxidized, of poor quality or simply used with too heavy a hand. It was something that both Anna and Olivia had to get used to, but now they drink it with delight.

Kenneth manning the caviar cart at Pearl Box; feeling at home with my Martini and candy cigarette
Kenneth manning the caviar cart; feeling at home with my Martini and candy cigarette
Amanda Gabriele/Tanner Tompkins

“We were sitting in the Waldorf, and Giancarlo Mancino was educating the staff on all six of his vermouths, and we were tasting them straight,” Anna says. “It opened up this whole new world for me. I grew up with my mom saying, ‘I like very, very dry. Virtually no vermouth. You know what, just no vermouth.’”

“Now I think vermouth enhances a Martini so much,” Olivia adds. “One of our signature cocktails is the Diretto Martini. It’s my favorite party trick to always have one in the freezer. Get your bottle of Holiday Vodka, take out 100 mL and pour in 100 mL of Mancino vermouth. Park it in the freezer, and you have a Martini whenever you want it.”

Before we call for the check (which arrives in a crystal ashtray with four candy cigarettes), we order the candy bowl, a brass and glass box overflowing with gummies of all shapes, colors and flavors. It’s certainly one of the most charming dessert orders in all of Manhattan. 

The time is 8:10 p.m., and we pile into a cab headed for Jean’s, the popular restaurant and nightclub on Lafayette Street. As we exit the car, I look up at the door and ponder, out loud, how I know the space. “I’ve definitely been here before,” I say to Anna.

“This used to be Butter,” Anna replies as she points to the former restaurant’s plaque that’s still inlaid in the sidewalk outside. “Iconic.” We both used to party there, so we spend a moment reminiscing as we enter the bar.    

Jean's famous chocolate chip cookie
Jean’s famous chocolate chip cookie
Amanda Gabriele

Even on a Wednesday night, the Jean’s dining room is booked and busy. We ordered a giant chocolate chip cookie with bourbon-infused milk, the Bunny Martini and vodka service for the table. Soon enough, our server pulls up with a cart of Holiday Vodka on ice, rocks glasses and orange slices. It’s not the nightcap I’m used to, but that didn’t stop me from topping off my own glass for seconds. 

As we pass around the Bunny Martini so everyone can taste, Anna tells us that Holiday scored their very first window display at Anthony Liquors on Spring Street. It’s quite the milestone, especially because Anna and Olivia used to peddle holiday door-to-door before they had a sales team.

“For the first summer, we were going around to random liquor stores and restaurants just selling it,” Olivia says. But we knew it wasn’t a long-term solution.”

a hand pouring a bottle of holiday vodka into rocks glasses on a white table with red menus
Holiday Vodka service at Jean’s
Amanda Gabriele

“We just installed a week and a half ago on Spring Street in a prime location,” Anna says about the window display. “We haven’t seen it in person yet, so we’re going tomorrow.” It’s a stunning design that’ll make you do a double-take — or, at the very least, make you wish you were on a beach somewhere holding a cocktail.

As we finish our vodka, we chat about summer plans, where we’ll be beaching and sightseeing along the way. Anna just got back from Saint-Tropez, and her photos are giving me wanderlust of the highest order. 

“Anna was on vacation for two weeks, so I tried not to talk to her and let her fully enjoy her vacation because those are the values of this company,” Olivia says. “It’s all about happiness, that true sense of the Italian ethos. It’s obviously the inspiration for the brand, but it’s also the ethos of how we are building and running the company.”

I can drink to that. 

Meet your guide

Amanda Gabriele

Amanda Gabriele

Amanda is InsideHook’s Senior Editor and has been writing about food, drinks, travel and style for 16 years. She’s written for Travel + Leisure, Eater, Gear Patrol and New York Magazine among other outlets.

More from Amanda Gabriele »

MEET US AT YOUR INBOX. FIRST ROUND'S ON US.

Every Thursday, our resident experts see to it that you’re up to date on the latest from the world of drinks. Trend reports, bottle reviews, cocktail recipes and more. Sign up for THE SPILL now.