Between the two of them, siblings Sylvi and Rob Roy seem to have worked behind nearly every restaurant bar in Portland (and beyond). That’s an exaggeration, but not much of one.

He: Fore Street; Petite Jacqueline; Central Provisions; Grace; Rhum; Bramhall; Broken Arrow; Grappa in Park City, Utah; Street and Co. – actually, there, his first restaurant job, he worked in the kitchen; and Primo in Rockland, where he has been for a half dozen years and now runs the bar program. “Plus a bunch of other little gigs in between,” Rob Roy says.

She: Legal Sea Foods and Summer Shack, both in Boston; DiMillo’s, where she spent five years; Eventide; Portland Hunt + Alpine Club, for almost six years; CBG; and, like her brother, Broken Arrow – strictly speaking, he followed her there.

When Sylvi Roy was in high school – the two are graduates of Deering High – she worked as a hostess and busser at Parker’s in North Deering, her first restaurant job. Her next job will be as head bartender/bar manager at the not-yet-open Twelve in Portland, a place Vogue magazine named to its list of America’s Most Anticipated Restaurant Openings of 2022. “I’m very stoked,” Sylvi said the day after she learned she was hired. “I was not even looking for anything.”

This March, Rob won both the People’s Choice and the Judge’s Choice awards at ChopTails, a charity cocktail competition at Batson River Brewing & Distilling in Portland, against several of the city’s highest-profile bartenders. It’s one of many competitions he’s won over the years. In 2019, Sylvi won the Northeast Regional Speed-Rack competition and went on to the nationals in Chicago. “She got in the top eight in the country,” Rob said proudly. She, too, has competed, and placed, often.

Their colleagues and friends call the two of them “passionate” about their work and used phrases like “dynamic duo” and “powerhouse pair” to describe the Roys’ mixology prowess. By the way, Rob hates the word “mixologist.”

“It definitely starts with her personality. She is warm and gregarious and sociable,” bartender Maeve Donnelly said about Sylvi; the two worked together at Hunt + Alpine and are now friends. Donnelly has since moved on to Crispy Gai. “She’s extremely kind and generous. She’s super competent. She somehow managed to complete every task behind the bar while also providing exceptional service to guests. Very effortless. She is known by practically the entire city of Portland as a bartender.”

As for Rob, he is “a central figure of an ‘old guard’ of hospitality professionals that was quietly putting Portland on the dining scene map before the secret got out to the rest of the country,” Batson River Portland General Manager Tom Barthelmes wrote in an email. “I’d put his importance to Portland’s reputation up there with Rob Evans (Hugo’s, Duckfat), Sam Hayward (Fore Street), Chris + Paige Gould (Central Provisions, Tipo). It’s not often you find a bartender’s reputation preceding them like that.”

PATHS CONVERGE

Sylvi, 37, and Rob, 36, grew up in Gray, Yarmouth and Portland. Their parents met while working as managers at the Ground Round in South Portland, a chain family restaurant with free popcorn and cartoons for kids, and they divorced while their own kids were still children.

Eventually, Sylvi and Rob would acquire a half-brother, 12 years their junior, but as kids, “It was the two of us,” Rob said. “We skied together. We cooked together. We did everything together.” They also played cribbage together (and still do, quite fiercely, according to observers), a game they learned from their maternal grandfather.

Rob was the quiet one. He describes himself as introspective, and his big sister as a social butterfly. Both were smart and did well in school, but neither spent a lot of time on homework. Sylvi loved art class and organizing parties for her high school class. Rob liked math class and baseball, and in middle school he formed a band. By high school, they ran in separate crowds.

Paradoxically, it was when Sylvi went off to college at Boston University that they grew close again. “It was really one of those absence-makes-the-heart-grow-fonder things,” Rob said. She studied graphic design and dreamed of a career as a painter or ceramicist. Two years later, Rob set off for the University of Maine in Orono to study biology. He’d excelled at science in high school and thought he might one day work in a laboratory.

“I ended up losing my spark for it,” he said. “The more I did it, the more I realized that I didn’t want to be stuck in a lab my whole life.”

After 2½ years, Rob left college and returned to Portland. Some time off – that was the plan. He got a job in the kitchen at Street and Co.

“What I thought was just going to be a placeholder, I fell into and loved,” he said. “I did everything from busing to food running to prep cooking to line cooking, before somebody gave me a shot at bartending.”

By that point, around 2007, he was thinking about a career as a cook, but, he confessed a little sheepishly, the money in bartending beckoned. He was at Fore Street, where on a busy summer night a bartender could take home some $350 in tips. It didn’t take long before Rob realized some other things about bartending: It offered the same creativity of cooking, but with something the professional kitchen didn’t have – a social aspect, a back and forth with customers, that he liked. “To me, it was the best of both worlds.

“That’s when I was starting to lean toward this as a career,” said Rob. “In the back of my mind, I was still thinking I’d go back to school. It was probably around age 25 I realized, this is what I want to do.”

Meanwhile, Sylvi graduated from college with a bachelor of fine arts in 2006 and cast about for a summer job. “The whole idea was to have a last hurrah, to go and have fun for the summer” before buckling down to real work, she said. The brother of a college roommate worked at the popular, upscale regional chain Legal Sea Foods, and he got her in the door for an interview.

“I got a restaurant job for the summer,” Sylvi said, “and the rest is history.” After just three months as a server, she moved behind the bar. One day, she served Legal Sea Foods owner Roger Berkowitz, whom she describes as “a very intimidating person,” a drink of her own devising, made from Grey Goose pear-flavored vodka with fresh pear puree, lemon juice and Cointreau.

“He ended up loving this drink,” she recollected. “My drink ended up on the menu at all 36 Legal Sea Foods at the time. It was called Sylvi’s Pure Peartini. Oh my god. It is so funny to think about. I’ve made much better drinks since then.”

Like her brother, Sylvi thought restaurant work was a detour on the way to a real career. “But I just never wanted the desk job,” she said. “Restaurants allow for fun, flexibility, traveling, networking. Every day is different.

“You are constantly stretching your brain in this industry. There is so much to learn,” she continued. Over the years between the two of them, Rob and Sylvi have attended sherry seminars, blind tastings, in-depth wine courses, and Camp Runamuck – a self-described “summer camp for bartenders” in Kentucky.

“There is something so creative about bartending,” Sylvi said, speaking about her start at Legal Sea Foods. “That’s what I loved about bartending.”

She said it in the past tense, but 16 years later, it’s still true.

WORK THEY LIKE

What makes a good bartender? In the last three decades as the craft cocktail movement has flourished – make that exploded – the job has become far more professional and demanding. Where once a bartender needed to know a comparatively small selection of classic drinks – such as Tom Collins, martinis, Old-Fashioneds – today she must be familiar with thousands of products and dozens of techniques, things like boutique spirits, custom ice, foams, fat-washing, flaming, barrel-aging, scratch ingredients, infusions of all sorts, bitters by the hundreds, fresh herbs (including unusual ones at Primo, like sweet cicely), and dehydrated fruit powders and garnishes. This barely scratches the surface.

Once upon a time in the music industry, you could simply sing, but needn’t write your own songs to be taken seriously. Similarly, high-profile modern bartenders need to not only know how to make the classics, but must also be skilled creators who can build their own balanced, beautiful and creative signature drinks. “You’re a chef behind the bar now,” said Lyle Aker, who co-owns Broken Arrow with his wife, Holly Aker. She bartended herself “for a really long time,” but said ruefully about the menu of creative cocktails at Broken Arrow, “(I) can’t make any of these drinks. None.”

Good bartending has both a technical side and an “emotional quotient,” according to Portland resident Alex Day, chief operating officer of Gin & Luck, which runs a national cocktail consulting company and operates Death & Co. cocktail bars in New York, Denver and L.A.; the company is opening a bar and restaurant in Portland, planned for late June, in the former Little Giant space.

Among the requisite technical qualities, Day listed are “working with intention, mastery of space, fluidity of motion, execution of drinks.” Also, maintaining a clean bar, no matter how busy the evening, a task Day described as “almost Sisyphean.” That’s the short version.

Day defined the emotional part of the job this way: “Engagement. It’s what the word hospitality means, but it’s so much deeper. Every really good bartender is constantly scanning the people and the space for opportunities to connect.”

Curiosity is another quality Day says is paramount. “It’s essentially being a lifelong learner,” he said. “If you’re curious about things, you’re going to want to go a little deeper, which is critical in my business.”

According to all accounts, Sylvi and Rob Roy check all these boxes, which you can see for yourself if you watch them at work. They have the grace of professional athletes behind the bar: Even when they are working very hard, the effort is swift, balletic and invisible. Conversely, on a quiet early Thursday evening in late April, when they shared a Broken Arrow shift – so rare an occurrence that Lyle Aker posted a silly Instagram invitation for it – they were always in motion.

“It’s just constant,” Sylvi said. “If you ever find a point that you are standing around, you are not good at your job.”

They wiped down the bar; checked glasses for spots; filled and ran the rapid bar dishwasher (two minutes per cycle); and meticulously repositioned their jiggers, shakers, strainers and barspoons after each use so they could grab them with no awkward scrambles. Sylvi is left-handed, so sets up her space (“the well” in bar lingo) to accommodate that, a trick she said she was taught by another left-handed Portland bartender, Hunt + Alpine co-owner Andrew Volk. Bottles in the well are always returned to the same spot, but as insurance, both Sylvi and Rob have memorized the shape of the necks and the look of the foil on each of the 30 or so bottles in the well at Broken Arrow so they can be sure to reach for the right one without a conscious thought. At a busy bar during service, you can’t stop to read a label.

“Working a shift making craft cocktails, it needs to be a dance,” Sylvi said. You learn that dance through thousands of hours of “practice and repetition, every day looking at, how can I make things smoother than the day before?”

While making drinks, Sylvi and Rob constantly scanned the bar, and they engaged customers – those they intuited wanted to engage, that is – with an admirable mix of good manners and fun.

“They are exuberant and bubbly and fun to be around,” said Primo executive chef and owner Melissa Kelly, who knows Sylvi through Rob and has hired her on occasion to work special events. “They are serious about their work, but in a very happy way.”

But bartending takes its toll, physical and mental. Bartenders stand on their feet for hours, lug heavy bottles and repeat a set of drink-building motions over and over and over.

New Year’s Eve marked Sylvi’s last shift at Hunt + Alpine, a spot that’s been on several lists of best cocktail bars in America. After nearly six years there, she was running the bar program but was sorely missing the creativity of “having my hands in. I was trying to put too much pressure on myself to do a job that I wasn’t fully capable of doing,” she said. It’s not an experience she likes to dwell on, and she is quick to credit Hunt + Alpine with her craft cocktail education and many happy memories. “I burnt myself out. I wanted to do everything at once. I couldn’t do that.”

From years of shaking drinks near her ears, Sylvi suffers from tinnitus. She’s adjusted her shaking stance, moving the shakers nearer her chest, and bought ear plugs that minimize the noise of shaking ice but let in the voices of patrons and co-workers. She and Rob stretch before shifts (and during shifts, if there is a quiet moment), are conscious of their stances behind the bar, and get massages several times a year.

Aches and pains aside, it’s work they like. “You are never going to be happy in this business unless you want to be there,” Rob said.

FAMILY TIES

Sylvi and Rob come from a family of cooks, and they approach bartending from both a culinary and a farm-to-glass perspective. Their late father, also Rob Roy, was a wonderful, adventurous cook who introduced them as children to “cool, weird things to eat,” Sylvi said, like artichokes and dragon fruit. When Sylvi got her first apartment, he taught her to cook. When his son worked at Fore Street, Rob Roy Sr. loved going there and ordering “a Rob Roy (whiskey, sweet vermouth and angostura bitters) made by Rob Roy for Rob Roy,” his son said, “and he didn’t even like them. But he thought it was so funny.”

Their late stepfather was executive chef for Aramark at Unum for 22 years. Their mother and aunt – sisters – bake and sell pies every summer from the family home in Somesville on Mount Desert Island, a town their ancestors founded a few hundred years ago, after the native Americans, “of course,” Rob hastened to add. The two sisters briefly sold their pies in Portland, too, from a storefront on Exchange Street.

When Rob Roy Sr. was dying, Sylvi Roy returned to Portland from Boston to nurse him. Both brother and sister adored him. He was their biggest influence and their biggest cheerleader, and they were his “No. 1 priority,” Sylvi said.

Rob Roy Sr. died a decade ago, at just 58, of cirrhosis of the liver, a disease that is usually caused, as it was in his case, by alcoholism. His children say his drinking never affected them, and Rob thinks his dad did his hard drinking as a young man (and musician) before they were born. Did they think their father worried about them choosing a career in which they are surrounded by alcohol every working day? Rob said he hadn’t thought about it that way. Sylvi said in part because of her father, she drinks only in moderation and, for stretches of time, not at all.

This isn’t easy for them to talk about.

“Truly, I never thought of him as an alcoholic,” she said of her father. “It came as a surprise to me when I read that on his death certificate. I look back and think, I knew it was cirrhosis of the liver, but I didn’t really grasp why he was dying until I read it on the death certificate.”

On their dad’s last Father’s Day, the three got matching tattoos, Rob Roy Sr.’s “first and only tattoo ever,” his son said. Rob Roy Sr. designed the tattoo: a bass clef inside a treble clef, with one of the dots transformed into a star for “The Sneetches,” Dr. Seuss creatures with stars on their bellies, and the younger Rob’s favorite book from boyhood.

Sylvi had planned to go back to Boston after her father died, but instead realized “how great this city is. I don’t think I’ll ever leave again. If I were to leave, I’d probably move north, closer to Rob.”

“I need another bartender, Sylvi,” he joked with her. He is hiring for Primo. The legendary Rockland restaurant, which closes every winter, is scheduled to open for the season on May 13. “Want to come up here?”

The two think that maybe one day, they’ll open a restaurant bar together. But “together” is the operative word. Sylvi said it’d never work if her brother were her boss. “We know our limitations,” Rob laughed.

The two describe themselves as best friends. “We’re very close,” Rob said. “We share everything.”

“I definitely talk to Rob more than anyone else,” Sylvi said.

When asked about the Roy siblings, Primo’s Melissa Kelly said, “If I didn’t know better, I would have thought they were twins. They have a great relationship, and they share a lot in common, but there is a little bit of a competitive relationship as well. They share secrets and ideas,” Kelly paused and laughed, “but maybe not all of them.”

Rob Roy’s Turn it Up

Primo owner and executive chef Melissa Kelly praised Rob Roy for his knack for making fun, “really beautiful drinks tying all that we are together” and said she relies on his knowledge of bar trends, “which is definitely good because I am a 23-year-old restaurant and we have to stay current. He is always up on what is happening and what is new. How do you create something new and exciting all the time? I try to do it with the food, and we do it in the garden, and I really depend on Rob to carry the torch at the bar. If he has an idea, I run with it because I trust him.”

A word on ingredients: To make the garden thyme syrup, simmer fresh thyme in a base of simple syrup (equal parts sugar and water) for a few minutes. Take off the heat. Let the thyme steep while the mixture cools, then strain out. Last year, Primo came out with its own branded gin. Rob Roy worked on the recipe with Kelly, Primo Wine Director Paul Cook and Blue Barren Distillery in Hope.

Makes 1 drink

1.5 oz Blue Barren’s Primo Gin

.5 oz Aperol

.75 oz lemon juice

.75 oz garden thyme syrup

Top with soda in an ice-filled Collins glass.

Garnish with fresh thyme sprig and a lemon twist.

Sylvi Roy’s Go-to Daquiri 

“My go-to in all seasons is a classic daiquiri (rum, lime and sugar),” Sylvi Roy says. “The fun thing about a daiquiri is that there are all sorts of different rums out there that can make the experience different. A well-made daiquiri will always put a smile on my face. This variation has become my absolute favorite.”

Make sugar syrup by simmering together sugar and water in a 1-to-1 ratio, until the sugar melts. Try Demerara sugar here, Sylvi suggests.

Makes 1 drink 

1.5 oz. Plantation Stiggins

Fancy pineapple rum

.5 oz. Green Chartreuse

.75 oz. freshly squeezed lime juice

.5 oz. simple syrup

3 heavy dashes of Angostura bitters

Shake well. Fine-strain into a chilled coupe glass or your favorite vessel.