Fifth Avenue South retail shakeup worries longtime tenants

The face of Naples’ legacy shopping street, Fifth Avenue South, is changing again. Some of its longtime tenants worry its next coat of elan will erase local retail that was comforting, quirky and original. Some of those have already fled. Some of them have held on, determined to stay on the street that has become their home.

Fifth Avenue South, long associated with moneyed shopping and fine dining, has been through two makeovers that have brought successively more expensive stores into the mix. The first, in 1994, was actually initiated by the city, which hired urban planners Andrés Duany and Elizabeth Plater-Zyberk and created a CRA that encompassed Fifth Avenue South. The move resulted in two arts anchors — Sugden Community Theatre and what is now the Naples Art Institute — and several parking garages. But it also purged utilitarian stores such as its camera shop for boutiques, galleries and restaurants.

Downtown began to change again with the purchase of buildings by Hoffmann Commercial Real Estate beginning in 2015. With it came the owners’ whimsical statuary, which proved to be a hit for tourist selfies, and the pledge that CEO David Hoffmann was investing in the community where he and his family had moved. His wife even opened a boutique, The Augusta Clothing Co., which operates at 601 Fifth Ave. S.

The clue that this may not be forever came at that time, however, when Hoffmann told a journalist that its real estate holdings were “very visual but a small part of our overall family investment strategy and portfolio.”

Then, in 2023, the company, now run by Hoffmann’s sons, Greg and Geoff, sold some 27 of their Naples addresses, including more than a dozen downtown, to the Aspen, Colorado-based M Development.

No word, but movement

At least one, at 651 Fifth Ave. S., was emptied out for a remodeling and tenants in several buildings were put on notice their leases would not be renewed.

Even a longtime retailer in a building not owned by M Development — Silver Eagle Gallery, a Native American jewelry and accessories store — moved away, possibly sensing an environment that would not work for it. Wind in the Willows, a Fifth Avenue South landmark clothier distinctive for its porcelain, script-titled facade, moved to a side street entrance in its 675 Fifth Ave. S. building to maintain a downtown presence after the M Development purchase. Its choice corner location will be replaced by a Faherty-branded store that sells upscale clothing, with men’s shirts starting largely at $150 and higher.

Regatta, a store popular for its one-of-a-kind gifts, moved north to 8799 U.S. 41 N., in The Marketplace at Pelican Bay at Vanderbilt Beach Road and U.S. 41 North after its address at 760 Fifth was purchased by M Development.

“Our lease was not renewed,” explained Vaida Gard, co-owner of the store that had been a fixture in downtown Naples since 1985. “They didn’t give us a reason. They just said they want basically corporate stores there.”

In the 630 building, another purchase by M Development, Joli Visage skin care fought in court to keep its space. And Aldo Castillo art gallery in the same building could only stay on Fifth Avenue by moving down the street.

The changes are part of a strategy, however, that M Development representatives hope will benefit Fifth Avenue South.

“We see retailers coming in and going to Mercato and places like that. We’d like to bring them back to Fifth Avenue, where there’s a lot of foot traffic,” said Derek Nagy, Naples property manager for M Development. “The big push is soft retail, as opposed to office. We’re trying to put a lot of retail on the first floor now.”

The company has taken special aim at larger spaces. The Regatta store was divided up, he said, into two, a flip-flop boutique and Spartina 449, a women’s wear company store. Another store it brought in is Johnnie-O’s, a casual menswear store where prices also tend to start at $158 for casual shirts.

“[We’re] just going to try to bring in more retail, because that’s going to drive overall activity and foot traffic on the avenue,” Nagy said.

The new business in the Castillo gallery space won’t sell soft goods, but small ones: East-West Sports Cards & Collectibles is moving there from its current location at 785 Fifth Ave.

“It’s very stressful,” said Castillo, who managed to locate another space, 472 Fifth Ave. S., next to Bar Tulia just three weeks before he had to vacate his Fifth Avenue South gallery or pay double the rent to renew his contract.

“I was paying $16,000 [per month] and it was going to go up to somewhere between $32,000 to $35,000. They said they had a tenant who would pay that,” he marveled.

The Nicaragua-born Castillo has been a longtime art presence in Southwest Florida. He was in Miromar Design Center in Estero for 17 years, and, in the last seven years, he had built up his second location in a roomy, 1,750-square- foot space at 634 Fifth Ave. S.

Until August 2025 Castillo kept both galleries, hedging his bets on the warning that Naples was too conservative in its art tastes for his narrative and process-driven art. Would they buy the Van Gogh self-portrait executed in buttons or painstakingly layered wood figures of pop culture icons such as Mickey Mouse in a matte red finish?

If there was an upside to Hurricane Ian — which flooded his current gallery — it was that it “also helped change or gave them an opportunity to remodel and to design something maybe more updated,” he said of Naples buyers.

Seeing empty stores

Castillo felt business on Fifth Avenue South was strong enough to consolidate his art to that location in 2025. But last season, by many businesses’ measurements, was disastrous. The ultra-jittery economy has been a double blow, he said.

‘“That’s why you see Fifth Avenue, one of the things that Naples is most proud of, with a lot of empty spaces that they own, you know, because the tenants have to move out because of this situation,” Castillo said.

Castillo thinks of himself as an educator as much as a gallerist, and for that, he likes foot traffic even if the visitors are not necessarily buyers. Fifth Avenue South is the perfect location, he said.

“Art has its own time. When I moved here, I was informed that most people were conservative, that contemporary art was not the trend. So, my job was to introduce that trend to Southwest Florida,” he declared. His pieces range from lean stone sculptures and lightbox paintings to “Pollock Climbers,” Ancizar Marin’s fiberglass characters clambering up their personal ropes in a colorful ballet.

“They use talent to communicate issues that we all need to hear,” he said.

On Nov. 1 they will be communicating from a different space.

“Most of these options in Fifth Avenue, as you can see, are dominated by these two landlords, right?” Castillo said, naming HF Companies, which still owns buildings, as the other. “So everybody who is coming to the area has to depend on that idea. It’s like a monopoly.”

Some newcomers in that same building are less concerned because their offices don’t need much inventory or they recently signed their contacts with NECO, the real estate management arm of M Development. Around the corner from Castillo’s gallery, Tiny Kitchen Empanadas, for example, opened this summer in the same building and was doing a brisk walk-in business with its fresh-baked, flaky Argentinean pies.

“We’re a month away from season, so I’m really excited,” said Alejandro Vega, who has owned the business in various locations over 15 years. He spins 33 1/3 records on a vintage player and churns out fresh beef, chicken, spinach-ricotta, ham-and-cheese and mushroom empanadas at a steady pace, even mid-afternoon. He said he doesn’t know who owns the building because he works with a landlord. “I’m a chef. I’m not real estate.”

And not every business that has left attributes it to M Development, at least publicly. The owners of Sushi-Thai, in the rotunda building at the Four Corners of U.S. 41 and Fifth Avenue South, closed it in June 2024, telling media it was solely their decision to concentrate on their other restaurants in the area.

Nagy also had good news for the patrons of L’Olivo, the popular trattoria at 651 Fifth Ave. S. that closed while M Development is upgrading the facade. The upgrade has been stuck navigating permitting differences with the city, but the restaurant will return, he said.

“They’re coming back, and they’ll have several other concepts, as well,” he said.