The Seasoned Pros

They play a vital role in elegant evenings and power breakfasts, in well-earned cocktails and late-night desserts, and in memorable lunches of the pre-beach, post-golf, and “ladies who” variety. They are on their feet for hours, oftentimes after working a day job, or before working a night job, where they’re also on their feet for hours. Through it all they are pleasant, knowledgeable, coordinated, and prompt. In the restaurant trade they are known as “the front of the house.” But to the rest of us they are...

Elizabeth Cecil

The purist:  Caitlin Lewis, State Road Restaurant, West Tisbury

When Caitlin Lewis hopped on a bus and moved to New York, she wasn’t sure if she was capable of staying in one place. After graduating from Martha’s Vineyard Regional High School, she rode the seasonal tide: a couple years of college in the winters, working Island jobs in the summers. When her hard-won tuition money ran out (she’d been saving since her first job as a chambermaid’s assistant at age eleven), she kept moving – one year, while snowboarding out West, she even did a stint as a Keno girl at an Apache reservation casino.

But Lewis stayed in the big city for ten years, moving up the ladder at celebrated Manhattan restaurants such as Lever House and Pastis. “In the city, everybody’s actors or models and they just happen to be waiting tables. But I got into restaurants where that wasn’t the case,” she says. “It actually is a profession, and it’s a trade, like fully – there’s training involved and knowledge involved. It’s not just slinging hash.”

When New York finally grew stale, she moved back to Massachusetts to finish her degree in English at Mount Holyoke College. With a diploma in hand, she returned home to the Island in 2010 and began building a full-time life here, closer to family. Lewis worked at several Island restaurants and, in her spare time, volunteered at Chilmark’s Grey Barn Farm and Mermaid Farm, where she learned to make feta. She also revived a passion for yoga.  

Now in her third year serving at State Road, Lewis also teaches yoga, both in the studio and on a stand-up paddleboard. And in her (limited) free time, she indulges another talent – cooking elaborate meals, complete with wine pairings.

At work, Lewis likes to keep it simple: “When you sit down at my table, I just want to show you a good time,” she says. “It’s just a meal, we’re not reinventing the wheel here, and I’m going to try to do everything for you that you need, before you even know that you need it.”

The Family Man: David Silva, Café Moxie, Vineyard Haven

David Silva has always worked hard to make a good life for his family. He grew up in Colombia, and when he was twelve his father immigrated to New York City to find work. With the allowance their dad sent back to Bogotá, Silva and his brother bought tools to start a business doing yard work and painting. He ultimately followed his father to New York, arriving a week before his seventeenth birthday and speaking no English. Within three days he had a job selling concessions at Madison Square Garden.

“My dad took me to the subway, bought me the tokens for the week, took me to work that first day, picked me up and took me back home, and the next day I was on my own,” Silva remembers. “You know, figure it out, just like every immigrant has to do when they come here – work hard and figure it out.”

New York was good to him – he met his wife, Martha, and they had a daughter, Alejandra. A French nouvelle cuisine chef took Silva under his wing and bumped him up from dishwasher to line cook, where he proved to be a deft hand. He shifted to front of the house jobs when he moved his family to Florida, where his son Andres, was born. There Silva advanced from busser to waiter to manager at prestigious West Palm Beach country clubs and restaurants, but he missed “trees, nature, and the seasons.” Like his father before him, he traveled to make better money to send home, taking seasonal work up north, eventually getting a job at Alchemy. And when he was offered a year-round position at the Edgartown restaurant, he leapt at the chance to move his family to the Island.

“My wife fell in love with this place,” he says of those first days on the Vineyard. “She never wanted to leave, but when winter housing ended we had a problem.” For a few years they struggled with the seasonal housing shuffle that is familiar to many Island working people. At last, after three years, the Silva name came to the top of the Dukes County Regional Housing Authority list. “Thank God, finally….If it wasn’t for the housing authority, we would have had to leave the Island.”

Silva stayed with Alchemy for eight years, and now serves at Café Moxie. “I just love people, I love taking care of people, making people happy,” he says of the career he began decades ago. “I love being around food, and I am familiar with the product.”

On the challenges of serving?

“God has given me patience and a lot of understanding.”

The Moonlighter:  Vanessa Vento, Dock Street Coffee Shop, Edgartown

Vanessa Vento had to tell herself to stop speaking Spanish to Island students while she was serving up breakfast at Dock Street Coffee Shop. But, to be fair, it comes with the territory when one is a dedicated middle school Spanish teacher and also a server at a popular local spot.

Vento first waited tables in her hometown of Haddonfield, New Jersey, while spending summers home from Loyola University in Maryland. Although she majored in Spanish and studied abroad in Madrid, she never imagined becoming a teacher.

“If you come out of college and know what you want to do for the rest of your life you are very fortunate, because I think you go through a process of finding yourself,” she says. “I was a shy person and really still am, and I looked at teaching as doing an eight hour oral report every day – not appealing to me in any way, shape, or form….And here I am doing the eight hour oral report every day. I don’t think twice about it, and I love it.”

Coming to the Island straight out of a four-year stint in a New York City cubicle, Vento started teaching a year into her Island life. She signed on at Dock Street not long after, and for the past twelve years, she’s balanced working summers and Sundays throughout the school year.  She now teaches at the Oak Bluffs School and is finishing up a master’s degree in teaching Spanish – as if she wasn’t already busy enough.

It’s not a schedule for everyone, but Vento appreciates her behind-the-counter perspective on the Island’s seasons. “Anywhere here on the Vineyard you have your regulars and then summer people, and at Dock Street, they’re literally sitting elbow to elbow,” she says. “And it’s nice to see the seasonal change, because [in August] there’s a line and it’s so busy, and then in February you know every face that comes in.”

The Free Agent:  Brendan O’Neill, Coop de Ville and Red Cat Kitchen, Oak Bluffs

“I have three lives in three different countries,” says Brendan O’Neill with his lively Irish lilt. “That don’t cross over.”

O’Neill, a staff fixture at Coop de Ville, spends his year moving between Spain, where he owns an apartment, his homeland Ireland, and Martha’s Vineyard, the island that gave him the freedom to globetrot. Once upon a time, however, he was a rooted Dubliner, a stolid Irish income tax officer with a staff of twenty-four. The first cracks appeared when a union-stipulated sabbatical took him to New York City and he found work as an Upper-East Side doorman, a bartender, an H&R Block accountant, and perhaps most notably, a flight attendant on the press corps flight trailing President Clinton around Europe. It wasn’t until he visited Martha’s Vineyard, however, that he got his first serving job and the inkling of a new career path.

“I liked [the Island] even on the boat ride over,” O’Neill remembers today, “and there were ‘help wanted’ signs in every window.” Chef Joe DaSilva at the former Standby Café in Oak Bluffs took a liking to the Irishman and offered him a summer job. “I discovered seasonal work for the first time ever, and that you can head off and do something else for the winter.”

For the past eighteen years he’s taken that seasonal schedule and run with it: “I’ve been to fifty-nine countries and thirty-five states.” And he rattles some of them off: “Every country in South America, a lot of Asia, Karachi, Pakistan – one of the top ten most dangerous cities in the world, but I managed to survive and have fun…got fined in Cuba for using my US passport.” The past ten years he’s spent winters in Cadiz, Spain, a Mediterranean town where he cooks (inspired by the chefs he’s worked for), entertains, takes street photography, relaxes, and reads.

And as for that tax career? “I did go back.” He cringes. “But five minutes in the office and I was like, ‘No I can’t do this.’”

“This doesn’t feel like work,” O’Neill says, motioning to the harborside scene around him – football (the other football) on the television screen and a parade of friends patting him on the back as they join the crowd. “I enjoy going to work every morning, every afternoon, hand on heart…Down at Coop de Ville I’m in shorts, T-shirt, sunglasses, Reefs, and I’m getting paid, overlooking Oak Bluffs harbor – it’s just special.”

The Up & Comer: Adam Rebello, Farm Neck Café, Oak Bluffs

Adam Rebello dreams of opening up a sports bar, or a local seafood restaurant with live music, or a burger joint, or of being part of a restaurant group that opens hot spots (he has a lot of ideas). He looks at the restaurant experience he’s gained in Oak Bluffs – bussing at the Ocean View, bartending at the Island House, moving from bar manager to assistant manager at Farm Neck Café, along with similar winter jobs in Colorado and California – as his education in the business. He likes his current job, but don’t be surprised when he hangs his own sign.

“The service industry, the restaurant industry, it’s in my blood,” says Adam, who was born and raised on the Island. “It comes naturally.”

That’s not just talk. His paternal grandfather, Anthony Rebello, owned Anthony’s Restaurant (now Hooked in Oak Bluffs), “which was the most popular restaurant on the Island back then,” Rebello says with pride. And then there’s his mother (and current boss), Mia Rebello, the Farm Neck Café manager.

“My mother is one of my best friends,” he says. “Her and I have gone through some tough times working together, and she’s never had an assistant manager, let alone having her son be assistant manager. Sometimes I overstep my boundaries, [talking] in a way that I would never talk to a manager who wasn’t also my mom, but we’re learning. She’s the hardest worker I know, and it makes me work even harder.”

His own management style didn’t fall far from the tree, and Adam takes the job in stride, fielding a slew of questions from his staff, even in the quiet hours of a midweek morning.

“I like to think that I can be a hard-ass, but I’m so loving, and I’ll be the first one to joke around, but when it’s time to work, it’s time to work…and when your staff wants to work harder for you, that’s when you know you’re doing your job.”

The Up-Island Allies: Whitney Swolinsky and Celeste Glavin, The Outermost Inn, Aquinnah

Celeste Glavin and Whitney Swolinsky have been friends since the beginning of their lives: “We have a picture of our moms naked on the beach, and she was just born, so her mom’s holding her and I’m still in my mom’s belly,” says Swolinsky with a laugh.

Growing up in Aquinnah and facing the pangs of being oh-so-far from down-Island divertissements forged a close bond between the women, who can piece together their history of summer jobs on the Island in tag-team fashion, one filling in the blanks for the other. There were high school summers working at the Menemsha Galley, “where we gained twenty pounds,” or as parking lot attendants at the Aquinnah public beach, “where all the cool kids worked,” and at the Beach Plum Inn, where they had their first table-side serving experience.

Today they work together at The Outermost Inn in Aquinnah, Glavin as the hostess and receptionist, Swolinsky as a server. Both also have positions in family businesses. Glavin, who studied design and engineering at Lehigh University, does research, product purchasing, and design for her father’s Vineyard Haven contracting, building, and design firm, Deca. Swolinsky, who has a psychology degree from Stanford, rents and delivers boats through her mother’s Menemsha-based business, Book-A-Boat.

Both have dabbled in the professional world off-Island. Swolinsky spent her first post-college year at a marketing firm in San Francisco, but escaped to the Island in time for the next summer. Glavin, meanwhile, travelled to Europe two separate times to join a team that was designing and pitching concept furniture, working for a couple that she connected with during their month-long stay at The Outermost Inn.

“[At the inn] you meet so many people, and they always want to tell you their stories and how they got to where they are, it’s almost like a giant informational interview,” says Swolinsky. “And its hard to quit, it’s hard to say: Next summer I’m going to be in an air-conditioned office, I will not go to the beach, I will live in New York in a sweaty subway.”