Carrying on: Siobhan Cleveland continues mom's legacy at Naples restaurant she began

The death of a loved one. Moving. Job loss. The pandemic. 

Medical experts consider any one of these events among life’s most significant stressors.

Now imagine all of the above impacting you within a span of 18 months. And having your first baby.

That’s what happened to Siobhan Cleveland, owner of the Real Macaw in East Naples.

And then came Hurricane Ian.

Hurricane Ian:Feeding family, neighbors is priority for Isles of Capri restaurant owner

Restaurants battered:Hurricane Ian: Did Doc Ford's, Bubble Room, other Sanibel, Captiva restaurants survive?

It began like a 'normal' September 

Like many Southwest Florida restaurants marking September for vacation and refurbishment, The Real Macaw closed Sept. 12 for just that, but there was little rest for this hands-on owner.

Cleveland spent her days earlier that month working on upgrades to the property, learning how to maneuver a forklift through gravel for landscaping duties among other priorities, including a refreshed dining room. 

She developed her work ethic while growing up as a snowbird, born on Cape Cod, Massachusetts, where her parents Mike Murphy and Jeanne Harvey ran restaurants. 

Her Brooklyn-born mother quickly tired of the cold weather and was lured to the U.S. Virgin Islands to run a local tavern and ice cream shop in St. Thomas harbor where the family would spend winters.

When Cleveland was 5 and starting school, a former colleague of her mother’s approached Harvey about opening a Caribbean-style restaurant in Naples, Florida, a place she never heard of yet a similar set-up/situation to what she was doing in St. Thomas. 

Harvey flew up to see the complex of buildings where the upper porch was a greasy spoon called the Shady Rest on Bayshore Drive, far from the tony arts destination it's now recognized as.

Cleveland shared it was a rough part of town, formerly known as Kelly Road.

The deal also included Fred, the resident macaw.

Harvey transformed the dingy space into The Real Macaw, opening in July 1992. Described by locals as an "elegant hole-in-the-wall" fine-dining restaurant with white tablecloths, it quickly developed a reputation for being off the beaten path, offering something special and different. 

Cleveland gleaned much of her restaurant’s colorful history while wading through artifacts as she continued cleaning her cubby-sized office post-Hurricane Ian. 

Opportunity knocks

Cleveland graduated from Lake Park Elementary School, Gulfview Middle School and spent freshman year at Naples High School. A self-described nerd, she yearned to attend boarding school and was accepted to Tabor Academy in Marion, Massachusetts.

With her parents splitting up, Harvey couldn’t afford three years of tuition. Through the generosity of local philanthropists Patty and Jay Baker, friends of her mother’s from the Real Macaw, a scholarship funding Cleveland’s first year was provided. 

Cleveland remains grateful to the Bakers, who “gave me the gift of opportunity and education.” She credits Tabor Academy with influencing her life’s course. It’s also where she first met David Cleveland, a friendly schoolmate who would become her husband years later.

Cleveland earned a coveted spot at Charleston Fashion Week in 2013 when judges (including Fern Mallis who created New York Fashion Week) named her a finalist, which required adding four more looks to her collection.

Cleveland ultimately won her division, a feat that launched her fashion career. She moved to New York City, working for top luxury goods designers including milliner Eugenia Kim, Maggie Norris Couture and Roberta Freymann of Roller Rabbit fame, learning the processes from producing looks to selling garments wholesale and all points in between. 

Cleveland didn’t know it at the time, but these skills would come in handy during the pandemic.

With her precious spare time, Cleveland volunteered at the Metropolitan Museum of Art and took ballet classes at The Joffrey for fun.

“I know how fortunate I was not to be touched by tragedy or ugliness or anything like that for a long time," she said "I always had a feeling that the other shoe was going to drop at some point. You're like, life isn't gonna be this good all the time and you're not trying to be pessimistic or look for the other side."

She reconnected with David after sending him a happy birthday Facebook message and he invited her out for drinks. In 2016, the couple married, building a life together with thriving careers and a chic apartment in the East Village.

All was smooth-ish as silk until March 2020 and the global rise of COVID-19. 

”It was very apocalyptic in New York City and I wondered what was going to happen. Are they going to close the bridges like they did after 9/11? Are they going to lock the city down? Because that’s where it was really spreading at first and all store shelves started clearing out.”

Like a science fiction movie

A “palpable sense of doom” loomed, so she packed masks and purchased plane tickets for Florida to visit her mother, who was sick. Just how sick, Cleveland didn't know until arriving.

“I remember leaving our apartment and saying to my husband, honey, grab our passports, grab our birth certificates, heirlooms and jewelry.”

He said, “Come on, we’re going to be back in a week. This isn’t a big deal.”

Cleveland had a hunch otherwise, describing it as living through a science fiction movie, knowing she might not return.

At the time, she also didn’t know how far mom’s battle with small cell lung cancer had progressed; Harvey's doctors offered a prognosis of 60 to 90 days. 

She told mom, “Let me be in the restaurant for you and you stay home. You shouldn’t be around people right now.”

A few days following her arrival in Naples, Cleveland discovered her job no longer existed when the high-end department stores (including Neiman-Marcus and Nordstrom’s) she worked with canceled hundreds of thousands of dollars in orders and were shuttered during the lockdown. 

She described it as a major life pivot: “I found myself in Florida staying with my mom, my husband, no job. I started helping at the restaurant, which closed within a week of Florida’s lockdown. And through that, I started brainstorming how to keep the restaurant afloat.”

Using her fashion career expertise, she created a dry goods marketplace at The Real Macaw. When store shelves in Naples were depleted of sanitizers, soap, toilet paper and the like, she recognized the restaurant’s suppliers had what people were looking for.

“I realized there’s a need here. Let’s connect people with these things and offer them at cost. We did a lot of contactless delivery. I was driving around dropping off bags of soap and all sorts of things to people.”

During this time, and with tremendous help from local interior designer (and Myra Janco Daniels’ former house manager) Ryan Warner, the couple completed Harvey's pre-pandemic kitchen renovation and other long-planned refurbishments.

“She had all these projects that she wanted to do that obviously she couldn’t get around to doing.” 

Cleveland wanted her mother to be as comfortable as possible. 

On May 4, 2020, Florida allowed restaurants to re-open opened with restrictions, and Cleveland became the Real Macaw’s bartender. Staff and patrons nicknamed her “the warden,” always asking where's Jeanne? 

One gent went through Cleveland to ask her mother out; she had to explain that mom’s not going on dates right now without delving into why. 

“We were hoping mom’s illness would follow a positive trajectory," she said. "And to some extent that was true for a while.”

After seven months of living out of suitcases packed for a weeklong visit, the couple returned to New York, trying to gauge the city's vibe and decide if they had a future there. They also visited David’s close-knit family for the first time since the lockdown. By the end of the trip, both realized they should be in Florida more to be with her mom, and see how things play out. 

And when Harvey should have been resting at home, she left the house and suffered a slip and fall in a Publix parking lot, resulting in a broken clavicle. “Once you get another injury and you’re already sick, it’s not good.” 

The couple purchased a condo close to the Real Macaw and her mom’s home when Harvey took a turn for the worse. “One week we’re getting our nails done together and then the next week she went into the hospital and never came back out.”

Harvey was airlifted to Tampa’s Moffitt Cancer Center where exploratory surgery revealed her cancer had severely spread. “Once it ignites, it’s like wildfire. It proliferates and there’s nothing you can do. She couldn’t breathe because of tumors blocking her airways. It was awful and terrible.”

Concurrently, Cleveland was earning her master’s degree in strategic design thinking and management, offered by Parsons/New School’s Paris campus.

As someone who likes keeping busy, she’d be at Moffitt with mom or in the restaurant's office participating in classes and lectures with 17 other students “a cohort of all with different backgrounds” who hailed from India, Taiwan, Saudi Arabia and Lebanon. 

She considers the program an amazing distraction from everything going on.

"It was a whole other supportive community that was more than just academic in terms of the friendships we made and the experience," Cleveland said.

An emotional rollercoaster

Jeanne Harvey died March 15, 2021, in Tampa. Cleveland returned to Naples the next day “because we have a business. Chef Dereck "Tebah" Brewley is like family and worked with her for all that time. He’s originally from Tortola and met mom when they both worked at the Bird of Paradise on St. Thomas.

Cleveland told her staff she had no plans to close the restaurant. 

“We’re going to get through this, we’ll host the memorial here," she said.

“It was a totally crazy time," she said. "The hardest emotional component was living in this place that I always associated so much with my mother and not having her around.” 

A few weeks after her mother's death, Cleveland discovered she was pregnant.

“I don’t know if it’s human nature to mark those milestones for yourself," she said.

"And instead of just counting back the days since we lost her, I was able to count down the days until my daughter arrived. The shift in perspective was much needed at such a devastating time. It was a joy that was shared with all the staff too because we’re like family all of a sudden.”

Preparing to reopen but Hurricane Ian had other plans

After Ian hit, Cleveland would soon master wielding a sledgehammer: Sept. 28 marked The Real Macaw's planned re-opening, the day the hurricane landed. Her East Naples neighborhood and the restaurant, backed by a canal, took a beating from the storm. 

Cleveland initially re-opened the restaurant's open-air bar Oct. 1, but closed everything Oct. 6, when she realized how massive the undertaking was to clean the compound that she describes as total devastation with mounds of trash. 

She will also get back on the forklift: all the new plants and surrounding shrubs, including those surrounding her mother's memorial plaque, didn’t survive the storm.

Cleveland credits her mom’s longstanding team with getting the restaurant back to normalcy. In addition to Tebah who she calls the uniting force in creating continuity through all the recent hurdles, there’s general manager David Krebs; her “talented, take-no-prisoners” bar manager Olivia Bennett; and Tracy Belford-Bartholf, one of her mother’s best friends who jumped in after Jeanne’s passing to be the restaurant's bookkeeper and defacto “head whip-cracker.” Several of her musicians are serving double duty as on-site construction pros.

At home, bins storing her mother’s mementos and photos also flooded, causing “a lifetime of stuff floating around in the garage."

"You open a bin up and see the brown water that has a very distinctive smell. I didn’t know they were in the garage and especially since her passing, it just becomes more precious," she said "Just totally heartbreaking. And you realize what stuff matters and what stuff doesn’t. The photos were pretty much the only thing I cared about. My heart sank.”

With help from David, she dumped all the photos in a bathtub, sitting near it for four hours to go through, separate then rinse Jeanne’s childhood photos from the 1950s and '60s. She even found a Beach Boys concert ticket stub from 1963.

“I think of it as time traveling. There’s all this destruction and I was reflecting upon my mom’s childhood and life, and my childhood and life. And I see my daughter in my mom’s baby photos. It was a real emotional journey in a way I didn’t anticipate.”

Tender moments, tender memories

Some of the furniture in the restaurant's dining room came from her childhood home, including a French hutch that previously lived in Cleveland’s bedroom. Her teddy bears too, repurposed in the restaurant but soaked from Ian, had to be tossed. 

“The restaurant’s been here longer than any house I’ve lived in growing up," Cleveland said. "It’s more than just a business or the sum of its parts. It’s a home in a lot of ways to the chef who’s worked here 30 years and many of our customers. 

“Now that I'm in my mom's shoes, I'm wowed by what she accomplished. I think it's easy when you're a little kid to take for granted how hard your parents work for you to give you opportunities and to do things for you, especially in the restaurant business.

"I understand her so much more now and respect her more than I thought I could."

Cleveland is patiently and lovingly re-restoring the dining room as she did in early September, honoring both her mother and the Real Macaw’s legacy while evolving its Caribbean vibes. “I want it to feel like someone’s beautiful home.”

She kept the top of a hand-painted parrot piano that Harvey scored at St. Matthews House for the restaurant’s bar. When Cleveland posted a video on Facebook of the soggy instrument's bulk being carried out following the flooding, she heard from Southwest Florida artist Muffy Clark Gill who originally painted it for a local youth center and always wondered what had happened to it. Cleveland apologized for having to let it go.

Guests continue asking her about replacing Fred's successor Brandy, the very loud blue and gold macaw who died five years ago. 

That’s a hard no. 

“I have a baby at home now, so one thing at home occasionally screaming at me is enough," she said.

Her mother's presence lingers in poignant everyday gestures. Going through the file cabinet within her tiny office, Cleveland holds dear Harvey's hand-written menu ideas and schedules for musicians playing there, bringing mom back if only for a moment.

Before the storm and sledgehammering the walls, she shared, “We used to have mirrors throughout the dining room. I’d catch my reflection doing something like smoothing out a tablecloth and I’d almost see her in me.

"I feel there are layers of time overlapping each other when I can see the resemblance. It was challenging at first, but now it's a comforting feeling. It feels nice to be carrying on in her stead.”

Diana Biederman is the food & restaurant reporter at Naples Daily News. She understands living out of a suitcase because she's been living out of her Hurricane Ian go-bag since Sept. 28. Connect via dbiederman@gannett.com.