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How it became city’s coolest community

When winery-owning friends from Vermont were arriving for an afternoon visit in April, they asked me to decide on a meeting place for lunch.

Off the top of my head, I gave them three choices. Unintentionally, each restaurant was on Bayshore Drive.

Why?

It’s my favorite Naples neighborhood, mixing vibrant Old Florida vibes with fun things to eat, do and see.

It’s got personality.

It’s not just my opinion: In 2022, Bayshore Drive won statewide recognition from the Florida chapter of the American Planning Association’s “Great Places in Florida People’s Choice Award” based on its “sense of place, cultural and historical interest, community involvement, and a vision for tomorrow.” 

These women helped transform the Bayshore neighborhood

As for that vision? It comes from Bayshore’s entrepreneurs and visionaries.

Especially the women.

Years ago, when it was Kelly Road, the street had a different personality with a reputation as a hotbed of drug dealing, prostitution and homeless camps.

How did this neighborhood transform? Meet the women behind its renaissance.

The pioneer: When Bayshore was the ‘wild, wild east’

Officially, Karen Beatty is chair of the Bayshore Gateway Triangle’s Community Redevelopment Agency.

Unofficially, she is the resident historian who arrived in Naples from Tampa in 1977 as the town’s second massage therapist before wellness became trendy.

She’s lived on one of Bayshore Drive’s side streets since 1988, all because of a magnificent tree.

“I love the old Florida feel,” Beatty said. “Unfortunately, a lot of that’s disappearing in Naples.”

She met her ex-husband Dale, an artist, at Squeeze Me, the juice bar he owned in Tin City.

The couple lived in Old Naples before heading to Bayshore because he wanted to be on the water, but not the beach.

‘Dangerous area at the time’

She had been scouting neighborhoods, wanting to build a portfolio of rental homes.

“It was a pretty dangerous area at the time. A stripper from Fort Myers was on Bayshore to buy drugs and convinced my young daughter to let her in to use the phone.”

In moments, Beatty realized her wallet was gone.

Even though the couple divorced, they jointly owned Haldeman Creek Fish House that served two purposes: his home, with proximity to Karen for co-parenting the kids, and for two months a year, as a mullet distribution center for local fishermen. She recalls beautiful old fishing boats that she’d see.

In a few years, it would become Dale’s sculpture studio and gallery, where the now-ex-couple hosted the first Up the Creek Art, Music, and Seafood Festival in the late 1980s.

It was so successful that the ex-marrieds hosted another the following year.

She describes this time as the beginning of Bayshore’s transition. She also credits past Collier County Commissioner Donna Fiala with being the street’s early advocate, with arts and culture as a focus.

She very much wanted this area to be an art district, and this was before the CRA started around 2000,” Beatty said.

‘Florida funky atmosphere’ began to take shape on Bayshore

Beatty recalled how Three60 market was The Tipsy Seagull, and The Real Macaw was The Shady Rest, a breakfast dive her family frequented on Saturday mornings.

“We were really into healthy food; it wasn’t particularly the healthiest food, but we liked the old Florida funky atmosphere,” she said. “It was a little taste of authentic.”

Beatty remembered that in the early 1990s, Jeanne Harvey bought The Shady Rest and nearby other homes, combining them with a courtyard in between to make it The Real Macaw.

The two became good friends “because we were pioneers in the area. We looked out for each other. We would sit on the deck of her restaurant, sip wine, and watch the crime and prostitution.”

Beatty worried about Harvey because “I knew she had money bags in there.”

“It was just the wild, wild east. For some reason, I was undaunted and trusted my gut that this area was going to redevelop and become something special.”

It’s why she joined the redevelopment board 20 years ago.

What also makes Beatty happy is seeing second-generation business owners continue their parents’ legacies.

Bohemian, eclectic spot in Collier County

One of her favorite Bayshore stories is Joel Toledo’s Green Door Nursery. She first met him at Mini Max, a Cuban market and general store owned by his grandparents and parents.

“It was very authentic, with groceries and a cafeteria serving the best Cuban sandwiches in the world. Growing up in Tampa with Ybor City, I love that culture and their prices were right. It was very special. Joel’s turned it into an incredible nursery.”

And Siobhan Harvey Cleveland has continued operating The Real Macaw since her good friend Jeanne’s passing.

What Beatty likes best about Bayshore Drive?

“You can walk out your door and surf the street for live music, art, great food, and a variety of things to do,” she said. “It’s one of the most eclectic, bohemian areas of Naples, if not the most unique.”

‘A bittersweet postmark of the passage of time and change’

Siobhan Harvey Cleveland, who now owns The Real Macaw following her late mother Jeanne Harvey’s passing in 2021, recently discovered photos taken when her mom opened the restaurant in 1991.

A toddler at the time, she recalls, it was “a rough neighborhood with a deserved reputation for illicit activities of all kinds.”

But mama Harvey, who grew up in Brooklyn, remained unfazed and had a reputation for being a tough cookie herself.

Harvey’s philosophy, according to her daughter?

“You don’t mess with their business, so they don’t mess with your business. She was a perfect mix of New York tough but also very sophisticated and worldly, which attracted a different clientele to this area.”

“You think about the people who are meant to meet a certain moment, and she was such a perfect fit for that moment in time,” Cleveland said.

Naples’ ‘coolest neighborhood’

Jeanne Harvey was attracted to Bayshore because of its proximity to downtown and the Gulf, thinking it was only a matter of time before the area would become a destination.

“It took a lot longer than she anticipated for things to come around. Old reputations die hard, and even now, we’re still fighting the reputation of when it was Kelly Road, which it hasn’t been in decades.”

Cleveland remembered the police presence at night from her tweens when she’d help her mom at the restaurant.

However, excluding occasional visits with mom, Cleveland hadn’t spent much time in the neighborhood since leaving for boarding school at 14.

Now in her mid-30s, she returned during the pandemic’s early days in 2020 and noticed a change for the good, describing a “palpable sense of revitalization and a renewed energy that seemed organic because it still had the same eclecticism and diversity.”

She watched people walking their dogs down the street, mothers pushing strollers, families at the Celebration Park food truck park and Naples Botanical Garden in all their glory.

As someone who lives where she works, why does she think Bayshore is Naples’ coolest neighborhood?

“It’s a mix of rebelliousness, confidence and authenticity. When you meet the business owners on the street, they all have those qualities. My mom had all that in spades.”

She added how they’re not afraid to “take a little bit of a risk and roll the dice.”

For Cleveland, it’s charming in a funky way that can’t be manufactured.

Her customers at The Real Macaw tell her they love it because there aren’t a lot of places “emblematic of old Florida charm anymore. Once you lose that, some of the history gets forgotten, but that doesn’t mean something better and more suited to the neighborhood as it is now won’t be wonderful. I think it’s a bittersweet postmark of the passage of time and change.”

Why are women leading the way?

“We’re sometimes forced to take the more uncharted path because we have less access to networking, funding, and things that make huge developmental projects easier for men to access,” Cleveland said.

“I think it’s a little bit of self-assuredness like I have this feeling, and I know that I can do it. It’s intuitive rather than simply cognitive.”

What also makes Bayshore attractive now?

“It isn’t so avant-garde or hipster Bushwick-esque or too industrial. It’s got this cool edge, and I think the women’s touch comes into that, adding refinement and a taste level that people see and want to be a part of.”

Her colleagues thought she was foolish

Diane Sullivan first arrived in Naples in 1982, residing here until leaving in 2000. She returned, making it her permanent home in 2011.

She worked at a prestigious real estate firm but wanted to open an independent brokerage. Her first thoughts were Old 41 Road in Bonita Springs or downtown Fort Myers.

But she settled on Bayshore Drive.

Her now former colleagues at Sotheby’s thought she was foolish.

“They thought it was dangerous, and there wasn’t any money to be made here.”

She joked that with so many Realtors fighting over the “12 rich people west of 41,” she now has her niche and has done $70 million in business in Bayshore.

“Irene Litchfield, who owned my building on the wrong side of the tracks, was the catalyst in changing the name of the road,” Cleveland said.

Sullivan bought the building. In the early days, “a lot of drunks” used it as a place to sleep. Initially, she was afraid, but she got used to it, rousing them to move when expecting clients.

She wanted an “Andy Griffith Show” vibe, where people would stop into her businesses just to say hello.

In addition to Naples Beach and Bay Realty, she also owns The Gardenia House since 2017, a 10-suite waterfront inn. The building is also home to her office, Bean to Cup coffee shop, and Hair4 You, a salon. On Sundays, Bayshore Jams is hosted at the inn, where locals and tourists gather for live music.

Along the way, she’s bought dilapidated homes to renovate and flip. A current project is zhujing up the 4,000-square-foot Bayshore Warehouse adjacent to her 2023 purchase of Bayshore Laundry. The space will have artist studios, galleries, and live/work residences inside and is planned to open in late May.

Her kids would tell her, “Mommy, you’re playing Monopoly in real life.”

Her motivation: Breathing a second life economically and aesthetically into what she describes as Naples’s rare working-class neighborhood.

She, too, was a big fan of Jeanne Harvey.

“More than anybody, Jeanne was the catalyst of change on the street when she opened The Real Macaw. She was as tough as they come, a stunning beauty and no-nonsense. I loved her, but many others didn’t understand women like her.”

She also admires Rebecca Maddox, who said to Sullivan, “Smart woman. Hit the ball where they ain’t.”

When deciding to live and work here, she said, “I love the real feel of the neighborhood.”

On comparing it to Port Royal, “We share the same body of water. I knew with certainty this is exactly where I’m supposed to be.”

Run the World (Girls): Nodding to Beyoncé, 14 Bayshore Drive businesses owned by women

Finding bliss: Naples Botanical Garden, anchor of Bayshore Drive

“I’m an entrepreneur, not a restaurateur”

That was a phrase repeated by Rebecca Maddox during a panel discussion on leadership in March.

Arguably Bayshore Drive’s most recognized business owner because of Celebration Park, Rebecca’s Wine Bar, Three60 Wine shops and her private club The Maddox; Maddox insists she’s an entrepreneur, not a restaurateur.

She still owns the building that was home for 13 years to Three60 Market, her first business on the street, whose last day was May 1. She is leasing it to Carolyn and Barry Larkin, who will open Seventh South Waterfront later in 2024.

She found the notion that women aren’t risk-takers “extremely interesting,” especially when it comes to Bayshore Drive.

“Over my career, I’ve learned that most men will take a P&L and analyze the shit out of it, then say sales aren’t where they should be. They have very little ability to say but in another year, this place will be rocking. They typically then don’t invest.”

A woman will say, “Yeah, I see the numbers, but I have this intuition that it will work.”

It’s why she believes more women on Bayshore Drive operate their own businesses.

“At the end of the day, any great success in business has a little bit of gut and belief in yourself that I can make this happen.”

Many told her a high-end deli wouldn’t work.

It did, although she didn’t have any walk-in traffic in the beginning, making it more of a destination for residents in other neighborhoods.

But that changed, and nothing pleases Maddox more than to see people who reside nearby walking and biking from business to business around the clock.

She’s witnessed the street’s transformation and gentrification, crediting Naples Botanical Garden as its anchor and providing the allure for a potential Pavarotti Foundation location.

When one builder told Maddox she “got so lucky,” she remembers telling him she worked her butt off.

“The people who really worked hard here were the women. Now builders, developers, and money guys are coming in and buying it up, saying how smart they are. It’s ironic for sure that we paved the way for the big boys to come in.”

‘There’s only so many diamonds you can sell from your dining room table’

After being terrified from her 911 experience working in New York City as Avon’s senior jewelry designer and seeing AAA magazine’s story calling Naples the next Palm Beach, Amanda Jaron moved her family from New Jersey’s suburbs to Golden Gate Estates in 2004, leasing a design studio in North Naples with a fine jewelry shop in her home.

There were no kids on her street for her children to play with.

Her Martha Stewart-like fantasy of raising “fancy chickens and pygmy goats and tending a greenhouse” dissipated when she realized she was more of a city girl living in a then-desolate zone.

When a client arrived to pick up customized diamond jewelry. she told Jaron a turkey vulture was chowing down on an unidentifiable carcass in front of her home.

That was the last straw.

Growing up in Clearwater Beach and attending high school in St. Petersburg, she always dreamed of living on the water. In 2015, she found her fixer-upper in the Bayshore Drive neighborhood.

“When we moved here, the neighborhood was still very much in a transitional phase. People often said to me I wish I were as brave as you to move to that neighborhood.”

Why were folks afraid of Bayshore back then?

“It’s all about perception. Coming from Manhattan, this neighborhood did not look scary. And we also had no history of how it looked 20 years ago. This neighborhood now looks cute and quaint and eclectic, but the seat you’re sitting in right now was directly across from 10 acres of woodlands that was the largest homeless camp in all of Collier County.”

But she was finally happy.

The first week, when settling in, “a boy my son’s age rang our doorbell and asked if he could come out and play. I had tears in my eyes. Waving at someone while you’re walking your dog, knowing what’s going on next door has really been great.”

She now enjoys a walkable three-minute commute to work at her Bayshore fine jewelry showroom and design studio “where art meets bling” that’s shared with her husband Stephen, a general contractor.

The miraculous building makeover features a mural of a mermaid with diamonds, drawn by her and realized by local artist Marcus Zotter, who credits Jaron with igniting his commercial success as Naples’s go-to muralist.

It wasn’t always that pretty.

“It’s my understanding it was a boat repair center. But this property also has a building on the back. Someone told me drugs were being run through these canals and brought to the building in the back.”

From C-suite executive in Basel, Switzerland to Bayshore gallerist

Catherine Ehrenberger ended up in the Bayshore area because when retiring in 2018 from her corporate job in the personal care industry, a career that took her around the world to live and work, she wanted warm weather.

Like Goldilocks, she tried out Florida, renting homes in Sarasota, Siesta Key and Longboat Key, working her way south to Naples.

She visited friends in Windstar, a gated community on Bayshore, and liked it. She and her husband, Ken, eventually made it official by purchasing a home there.

After a year and a half, Ehrenberger changed her mind about retiring and opened “Things I Like by Catherine,” one of the coolest spaces anywhere in Naples.

Why return to the workforce?

“I have always been an art collector. I bought my first piece of original art when I graduated college and it’s still hanging in my house. I think I knew when I retired that I wanted to have an art gallery because I wanted to be surrounded by it.”

Why Bayshore Drive?

“I wanted a place where I could ride my bike to work,” she said. “I spent my whole life flying and living everywhere. In this chapter of my life, I want to live where I work, be part of the community where I work, and put roots down. I never was able to do that before.”

She credits Rebecca Maddox who dubbed the Drive as the “SoHo of Naples” boasting boutique independent businesses and art.

“When I heard that, I thought this could be the place for my vision of an art gallery. I wanted a welcoming space where people could come in and experience fine art that I, as a collector, had not.”

Her space was formerly a home that took two years to renovate. She also wanted something elegant but in an area that had diversity with a “lower key, more relaxed vibe,” citing Naples Botanical Garden, Celebration Park and Amanda Jaron’s studio.

Her wish and intention?

“That people are delighted with their experience here, from walking up and smelling the jasmine vines on the building’s pergola to coming in and seeing all this eclectic, joyful art.”