Rebecca Maddox – Building an Empire on Food and Conversation

Rebecca Maddox has done it again. The entrepreneur who helped to transform the Bayshore corridor in East Naples with her dining and drinking establishments has just opened her most ambitious project yet. 

The Maddox, an upscale members-only social club, made its debut on October 3 behind Rebecca’s, a wine bar that also hosts Three60 Wines, across Bayshore Drive from the original Three60 Market and Celebration Park, a waterfront collection of food trucks plus an outdoor bar. 

Even on a Tuesday in the depths of the offseason, numerous members sipped, nibbled and mingled inside the new club as a four-piece band played standards and bossa nova.

Back in the dark ages of the last century, what is now Bayshore Drive was called Kelly Rd., and the area had a reputation. For those who lived in Naples proper – and Naples was very proper – the name Kelly Road was synonymous with low rent, undesirables, even “hookers and crack cocaine.” Collier County created the Bayshore/Gateway Triangle Community Redevelopment Area and mentioned in their redevelopment plan the definition of a “blighted area, in which there (are) a substantial number of slum, deteriorated, or deteriorating structures and conditions which endanger life or property” due to factors including “unsanitary or unsafe conditions.” 

Bayshore Drive would not have been considered the obvious place to open a new eatery looking to attract the Naples crowd. Even though the corridor had been gentrifying, with the upscale Windstar Country Club development, the yachts of Hamilton Harbor along Naples Bay and the Naples Botanical Garden attracting nature lovers and eco-tourists, the stigma persisted. 

Along with those other economic drivers and change agents, Maddox’s restaurant ventures did a great deal to give a broad range of people incentive to visit Bayshore Drive. Donna Fiala, the longtime and now former county commissioner who represented East Naples as well as Marco Island, called Rebeca Maddox a visionary and said “everything she touches turns to gold. Other people sneered at her, but she saw the value in the area and what it could be made into. She had the insight to see it – after all, we’re all on the water here.” 

Three60 Market was Maddox’s first foray into Bayshore, and for that matter into the food and beverage business, opening in 2011 and serving casual gourmet fare where Bayshore Drive crosses Haldeman Creek, after Maddox bought the building, former home of the Tipsy Seagull, in 2010.

“Once I opened it, most people thought that no one with money would cross the (Gordon River) bridge. But they did – and it was really one by one by one. I talked to them, got to know them, and before long they were telling their friends, ‘go see Rebecca.’” Accessible by boat as well as car, it has become an increasingly popular fixture of the Bayshore corridor.

Three60 Market is locally famous for selling every bottle of wine with a markup of just $3.60, but that came after the business had been up and running for years, when the Naples Botanical Garden opened their Fogg Café, and the significant portion of Three60 customers sent from the Garden dried up. The wine business took an increasing share of the limited space at Three60, and when Rebecca opened her wine bar, Rebecca’s Cocktail and Wine Bar, in April of this year, they moved the bottle business to the new location. 

Before opening the wine bar – years before, in 2018 – Rebecca introduced her second Bayshore venture, Celebration Park, a grouping of food trucks plus a full liquor bar on Haldeman Creek across from Three60 Market. There was controversy about parking and commercialization, but the park has gained its own devoted following, with wildly diverse food offerings including seafood, gyros, Mexican, pizza, lobster rolls, gourmet burgers and a mac ’n’ cheese specialist. The fact that Celebration Park’s address is on Becca Ave., said Maddox, is merely a coincidence. 

So now, with the addition of the Maddox, Rebecca (the person) has food and drink offerings appealing to nearly every taste and a wide spectrum of price points. 

“She has something for everyone,” said Fiala. From gyros at Celebration Park, to Three60 Market, serving casual fare with only a couple of items topping $20, to the charcuterie and caviar setups of Rebecca’s wine bar, the food runs the gamut. At The Maddox, menu items are decidedly upscale, but that will not be a concern for anyone not willing or able to shell out the $18,000, plus tax, membership fee. And just having the ready scratch to pay the dues doesn’t get you in – no one will be admitted to the targeted 300 memberships without Rebecca’s personal endorsement. 

The concept for The Maddox, she said, started out as a wine club and evolved into a social club. “It’s about tastings, not just wine tastings,” but also including taste sensations such as sake, oysters and cheese. She is looking for a certain kind of person, someone she would want to spend time with herself – and her life revolves around her eateries. 

“I want people who are kind, a tolerant, fun-loving, diverse group. I want people who will come here regularly, not just throw a credit card at me, take out a membership and never show up.” 

Spaces at The Maddox are designed to foster repeat visits and conversation, with an upstairs champagne room, chef’s kitchen, meeting rooms and a downstairs central bar with doors flung wide to the outside when temperatures permit. 

Maddox spent her career in the corporate and financial world, not the restaurant or hospitality world. She had upper-echelon positions at Citi Corp., Guardian Life, Wright Management, Arthur Andersen, and was on the board of PNC Bank. 

“It seems dry, but I was always on the creative side of it,” she said. She also became a sought-after business and motivational speaker. She came to Southwest Florida in the early 1990s, and bought a home in 2001, just ahead of the 9/11 attacks. She has thrown herself into the food and beverage ventures with her trademark enthusiasm. Speaking of trademarks, Rebecca can generally be seen in white slacks, a long-sleeved shirt, distinctive cranberry red eyeglasses and matching lipstick under her shock of white hair.

Like everything else, she takes a hands-on approach to the food being served, and the Three60 Market features a “Rebecca’s sandwich” and “Rebecca’s salad.”

Maddox has expanded her horizons north in Southwest Florida and beyond. She has opened or is opening soon Three60 Markets on Trail Blvd. in Naples, another at the corner of Immokalee Rd. and Logan Blvd., and one in Estero. She and a business partner – and all her partners are silent partners, with the decisions solely hers – have purchased property in Highlands, N.C., with the goal to build out 15 to 20 separate locations. The one partner who is not silent is Nancy Maddox, Rebecca’s significant other, who is a regular fixture at Three60 Market. 

For Marco area residents, Rebecca’s eateries are nearby, a shorter drive than almost anything else in Naples. And despite the far-flung additions contemplated to her empire, you might say that Rebecca Maddox has left her heart in the Bayshore corridor.

“I want people to come in with some money to invest and continue to make this an eclectic street that people will come to,” she said. “I feel we have more potential than any street in Collier County.”