Naples entrepreneur Rebecca Maddox on Wednesday publicly launched Rebecca’s Wine Bar, the first of two eponymous ventures she recently built on Bayshore Drive across from her Celebration Park and Three60 Market.  

The new modern wine bar fronting Bayshore is open to the public with an actual bar, a charcuterie room and a Three60 Wine shop. A companion project, a private members-only social club named The Maddox, will open in October on the shared open-air campus at 2955 Bayshore Drive in East Naples.  

The innovative projects have been about five years in the making. Following a conception phase, Maddox & Partners purchased two vacant commercial lots in early 2019 totaling nearly 1.5 acres and the project broke ground in the summer of 2021 with architectural plans designed by David Corban of Naples. The entrance into the new venue on Bayshore lines up with Becca Avenue, the road at the entrance to Celebration Park and its adjacent parking lot.  

A 40-foot wine bar runs along the eastern edge of Rebecca’s. “I think it’s a pretty interesting bar. I think it’s different. It’s a cool space, a little bit more urban, indoor and outdoor,” Maddox said.  

She tapped Matt Johnson, the brother of Chef Todd Johnson of Nosh at Naples Bay, as her beverage director. “He has done a great job putting the bar together. I’ve known the Johnson boys for a long time. And so, I feel like we have a real superstar at the bar, superstar chef, and we know the wine business works pretty well, so I’m thinking it’s going to be packed.”Darren Veilleux, the former executive chef at Sails Restaurant in downtown Naples and a Johnson & Wales graduate, will oversee culinary creations.   

“He’s got a very small menu for salads and seven or eight cold chilled lobster, some crab, like artichoke and white bean dip,” Maddox said. “Our concept there is shareables. We’re using low glasses, putting the stuff in the middle.”  

Rebecca’s has a prep room for food but not an actual kitchen. “We’re not a restaurant but we are serving some food at the bar,” she said.  

Maddox said the concept is more about being social than dining out. “Let’s all get a cocktail, sit down and share a charcuterie board and whatever, some lobster,” she said.  

“The other thing we have in Rebecca’s is a glassed-in charcuterie room where we’ll be serving 17 cheeses and 17 meats. Really great stuff. I don’t think anyone in town has anything like it.”  

Rebecca’s also will promote caviar service at a reasonable price. “When most people hear caviar, they think hundreds of dollars. We have a beautiful setup for $80. So, we’re going to do a modern version, which is with potato chips, and then the traditional with the blinis and all the accompaniments.”  

Sean Smith, who opened Marea restaurant locations in New York City and Dubai, is the general manager of The Maddox Naples. Smith was busy this week with last-minute preparations for Rebecca’s.  

“We are thrilled to be the newest addition to the Bayshore area and hope to replicate the success and incredible popularity of Celebration Park and Three60 Market,” he said.  

Maddox thinks Rebecca’s is complimentary to her other properties on Bayshore. “When it’s pouring raining, which usually clears Celebration Park out, this is an indoor bar,” she said. “I think we’ll bring to Bayshore a whole different group of people who are going to say, ‘I like Rebecca’s better than the other two.’ And that’s great. I just want to bring them to Bayshore.” Three60 Wine  

Maddox thinks of her latest business growth in three parts.   

“We are moving our Three60 Wine business into Rebecca’s, so it will be Three60 Wine at Rebecca’s,” she said. “Anybody who shopped Three60 Wine on Bayshore knows there are boxes everywhere, and it takes us 20 minutes to find stuff. The new store, we’ve got 1,140 bottles on the wall, so you’ll literally be able to just walk around and go, ‘Oh, I see everything you have.’ Also, we have a state-of-the-art inventory system. It’s just going to make buying wine at Three60 so much easier.”  

The retail prices for bottles of wine will be the same as Three60 – marked up only $3.60. She opened a second Three60 Wine shop in North Naples in 2021 and plans to keep growing that concept. She has signed leases for two additional stores.  

“It’s totally the same concept. Nothing is changing,” she said. “All four stores – the two that exist and the two that are coming online – all have the same pricing.”  

Rebecca’s will be open 9 a.m. to 10 p.m. every day except Monday. Rebecca’s, Three60 Market and Celebration Park are all closed on Mondays.  

“We’re opening at 9 primarily because of the retail store,” Maddox said. “We don’t expect the bar to be hopping at 9.”  

“I’m trying to put together unique properties that literally whoever comes to Bayshore has a place to go,” Maddox said. “You know, I love Celebration Park. Celebration Park has done outstanding. I’m shocked how many people have heard of Celebration Park. But, it’s not for everyone. So, I want them to come to Bayshore and whatever their palate is, however old they are, how much money they have, there’s always a place that they can go to and enjoy on Bayshore.”Three60 Market  

“I’ve totally re-envisioned Three60 Market,” Maddox said. “So, once all the wine is out of there, we will have 150 seats, which allows us to get a liquor license.”  

Maddox doesn’t think that change will necessarily make Three60 Market a bar, but it will allow guests to enjoy a Bloody Mary, a screwdriver or another cocktail for brunch or dinner. Three60 also will continue to offer dinners, but Maddox wants to heighten the experience.   

“I want to look for ways that when people sit down and go home, they say, ‘That was really fun, and it didn’t break the bank.’ So that’s where we’re going with Three60.” she said.  

Maddox also plans to turn back the clock a bit to Three60’s origins and have a lot more market items such as French breads, seafood, lasagna and meatloaf because she has noticed that people aren’t dining out as much lately. “So, I’m going to go much more towards a market,” she said. “I’ve already started the process. So, yesterday, people were buying French bread, homemade strawberry jam that we literally just put on the counter. Just more stuff like that.”  

The cartons and bottles of wine were relocated this week to Rebecca’s across the street, leaving Maddox with a void to fill. “I want to have six, eight, 10 soups on the wall,” she said. “I want to do three takeaway dinners every night and put them online so that people can say you know, ‘Tonight I’m going to get two pieces of branzino or meatloaf and mashed potatoes.’ So, that’s the idea. We’re going to have a lot more takeaway market items.”  

“And we’ll still do breakfast and lunch and dinner for people who want to be there. But that’s the direction that we’re going.” The Maddox Naples  

Meanwhile, behind Rebecca’s Wine Bar, The Maddox Naples will open Oct. 1.   

“It’s not a target. That is the date we will open,” Maddox said. “I could have opened it right now, literally, but a lot of the members are going home, back north, and starting to travel, and I really didn’t want to open a club when everyone was leaving.”  

While Rebecca’s is open to the public, The Maddox is a private social club. It’s not a restaurant. “It’s for people who love doing things, and meeting people,” Maddox said. “I’m hand-selecting 300 couples to join. I do have some single people, so 300 memberships. I’m looking for interesting and interested people. And that’s a big statement, if you catch what I’m saying. You can be the most interesting person in the world, but if you don’t care about anything, about me, that’s kind of boring after a while.”  

The Maddox plans more than 150 wine tastings and 100 or so liquor tastings a year, Maddox said. “And what I mean by that is, for example, we’re going to do a sake tasting, and bring sushi rollers from Miami as the food pairing. So, it’ll be an event. It’ll be an experience.”  

“And then, of course, we’re going to do food tastings. So, there’ll be a lot of those different kinds of activities. We have an outdoor stage, where we’re going to bring a couple of hundred acts a year for the members.” Initially, The Maddox was planned to be much more wine-centric, but as Maddox started taking deposits for members, she realized it would be much more of a social club because, when asked, people wanted a venue to meet other fun people and do things together.  

Maddox does not have 300 members yet. “Some of that is by design because I don’t know who I don’t know,” she said. “Honestly, every day people come and express interest. And I never met them before. And my process is super time-consuming. So I have one of my guys take them on a tour and then I spend a couple of hours with them to see if I think that the club would be right for them. That takes a lot of time. But, I can tell you the members just appreciate it immensely. Because it’s not like, ‘Well, here’s my money.’ It’s like, ‘I will worry about that later.’”  

Maddox still has a vision to grow the concept elsewhere. “Assuming that it works, like I think it can work,” she said.  

Maddox and a neighbor, who also is one of the club members, already are setting the stage for a possible second location. “He and I bought 126 acres up in Highlands, North Carolina. So, there’s like a five-acre commercial piece.”  

Maddox realizes her dreams are sometimes difficult for others to envision. “When I was first talking about the food truck park, everyone thought I was nuts. So, until you do it, you can’t say, ‘Oh, here’s how it worked out.’ So that worked out really well.”