The corner of 675 Fifth Ave. S. has a porcelain facade with the shop's name written in script, and for years it meant Wind in the Willows. The clothier is still in the building, but its door is now on the side street. The corner is going to a Faherty store, where men's shirts start largely at $150 and up, Gulfshore Business reported in mid-October.
That move shows the pattern behind most of the changes on the avenue this fall. The businesses giving up their Fifth Avenue frontage mostly haven't closed. One went to a side entrance, one moved down the street, one went to Seagate Drive, and one went up U.S. 41. As the season starts, a regular's downtown route now covers more ground than the avenue alone.
Why the ground floors are turning over
Most of the change traces back to one purchase. In 2023, Hoffmann Commercial Real Estate sold some 27 of its Naples addresses, including more than a dozen downtown, to M Development of Aspen, Colorado. Its real estate management arm is NECO, and some newer tenants have signed their contracts with it.
Derek Nagy, the company's Naples property manager, explained the strategy to Gulfshore Business. "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," he said. "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 focused on its larger spaces, according to the same report. Some get divided, and the ground floors are being leased to apparel brands. That explains why the moves came in a cluster. Several longtime tenants had leases come up in buildings with the same new owner.
Where the familiar names went
| Business | Former Fifth Avenue address | Where to find it now |
|---|---|---|
| Wind in the Willows | Corner of 675 Fifth Ave. S. | Side-street entrance, same building |
| Aldo Castillo Gallery | 634 Fifth Ave. S. | 472 Fifth Ave. S., next to Bar Tulia, opening Nov. 1 |
| Silver Eagle Gallery | Fifth Avenue South | 780 Seagate Drive, open since Sept. 21 |
| Regatta | 760 Fifth Ave. S. | 8799 U.S. 41 N., The Marketplace at Pelican Bay |
| East-West Sports Cards & Collectibles | 785 Fifth Ave. S. | Moving into 634 Fifth Ave. S. |
Aldo Castillo stayed on the avenue by moving down it. He told Gulfshore Business that he had been paying $16,000 a month at 634 Fifth Ave. S., and that renewing would have cost somewhere between $32,000 and $35,000. He found 472 Fifth Ave. S. three weeks before he had to leave. The gallery had used a 1,750-square-foot space for about seven years. Before that, Castillo spent 17 years at Miromar Design Center in Estero. The new gallery opens Nov. 1. The Pollock Climbers, Ancizar Marin's colorful fiberglass figures, and the bronze sculpture pieces should be on view there for the season.
Silver Eagle Gallery moved on Sept. 21 to an expanded quarter-acre site at 780 Seagate Drive, the Naples Press reported. The store has 1,525 square feet inside. It carries Native American and traditional jewelry, sterling silver and gold, geodes, pottery and artwork, priced from $1 to $20,000. Owner Heather Neils told the paper the main reason for the move was security against future storm damage. She named M Development's purchases on Fifth Avenue as an indirect reason. Holiday shoppers who have bought gifts there every year will now find it on Seagate Drive.
Regatta, the gift shop that had been downtown since 1985, now operates at 8799 U.S. 41 N. in The Marketplace at Pelican Bay, at Vanderbilt Beach Road. "Our lease was not renewed," co-owner Vaida Gard told Gulfshore Business.
What opened in the old spaces
Regatta's former space shows what the new ground floor looks like. It was split in two. The Fifth Avenue South business district's June newsletter reported that OluKai and Spartina 449 opened there this spring. OluKai's own store locator lists its Naples shop at 762 Fifth Ave. S., so the two brands sit side by side across 760 and 762.
Johnnie-O lists its Naples store as open at 375 Fifth Ave. S. Hours are 11 a.m. to 7 p.m. Monday through Saturday and noon to 6 p.m. on Sunday. Gulfshore Business put its casual shirts at $158 and up. Faherty is still listed as the incoming tenant at the Wind in the Willows corner. Its Florida store directory does not list Naples yet, so the corner will likely look unfinished for part of the season.
Some of the replacements are small shops. East-West Sports Cards & Collectibles is moving from 785 Fifth into Castillo's old gallery at 634. Around the corner in the same building, Tiny Kitchen Empanadas opened this summer. Gulfshore Business found records spinning on a vintage player and a steady walk-in trade even in mid-afternoon. The shop bakes beef, chicken, spinach-ricotta, ham-and-cheese and mushroom empanadas. Florida Weekly's Naples Foodie gives the address as 524 Park Street.
The restaurant block that stays dark this season
OluKai and Spartina 449 were open in Regatta's old space by spring. A former restaurant row on the same avenue is still waiting on a building permit. The two-story building at 649–663 Fifth Ave. S., just west of Inn on Fifth, held L'Olivo and Roma until its interior was gutted in the summer of 2025. It has sat unfinished since then.
Tim Aten's Tim Aten Knows column in Gulfshore Business explains the holdup. Restaurateur Feibi Gouda, who ran L'Olivo for more than six years, plans to replace it with Riva Mediterranean Restaurant & Lounge at 651 Fifth Ave. S. and to open Zanu Sushi Bar in the old Roma space. Because the project counts as substantial redevelopment, the City of Naples treated the 60-year-old building as new construction, so everything had to meet the current building code. That opened questions on dry floodproofing and soil borings, and the permit application came back several times with comments.
Gouda said she hoped to have the construction permit by the end of October. She estimated six to eight months from the permit to opening, which puts both restaurants in a post-season 2027 launch. "We're losing the second season," she said. Her original plan had been to open in early 2026. The city's Design Review Board still has to approve the facade changes, although interior work can start before that.
The name on that space is unsettled too. Nagy told Gulfshore Business that L'Olivo is "coming back, and they'll have several other concepts, as well." Gouda's plans, as described in the Aten column, call it Riva. Either way, the L'Olivo team is coming back to the block under a new concept, and not before this winter ends.
November on Fifth, with the new addresses
The Fifth Avenue South events calendar fills up as the new tenants settle in, and several of the dates line up with the new addresses.
- Nov. 1: The Naples Concert Band plays Cambier Park, the same day Aldo Castillo Gallery opens at 472 Fifth Ave. S.
- Nov. 9: Stardust Memories Big Band plays the Cambier Park bandshell.
- Nov. 12: Evening on Fifth, with OluKai, Spartina 449 and Johnnie-O open on the avenue.
- Nov. 14: The Naples Artcrafters Fine Arts & Craft Show at Cambier Park.
- Nov. 15: Naples Big Band at the Cambier Park bandshell.
- Nov. 28: Art in the Park at Cambier Park, 10 a.m. to 4 p.m., a Naples tradition since 1957. The Naples Art Institute runs it as a juried outdoor art fair series.
Holiday gift lists need a few updates this year. Silver Eagle is on Seagate Drive, Regatta is at The Marketplace at Pelican Bay, and Wind in the Willows' door is on the side street.
When a block you know well starts changing, it helps to know what is opening, what is waiting on permits and where the old favorites moved. That is the kind of local tracking The Fowler Team does every season across Naples. If you would like to talk about how downtown is changing and what it means for your corner of town, Mike and Kylie are glad to compare notes. Discover Your SWFL Home.
