Alejandro Vega plays 33 1/3 records on a vintage turntable at Tiny Kitchen Empanadas while he bakes beef, chicken, spinach-ricotta, ham-and-cheese and mushroom empanadas through the afternoon. He opened this summer in a Fifth Avenue South building where two neighbors are leaving their storefronts. "We're a month away from season, so I'm really excited," he told Gulfshore Business this month.

The same article follows those neighbors out the door, so it's easy to read this fall as the street losing its regulars. Look at the actual addresses and most of the familiar names are a few doors down, a block over, or one shopping center north. The storefronts are being reshuffled, and almost all of the businesses are still around.

The Forwarding Addresses

Here's where the names Naples residents know are headed this season, based on Gulfshore Business reporting and the businesses' own pages:

Regatta made the longest move. It had been downtown since 1985 and now sits at Vanderbilt Beach Road and U.S. 41 North. Anyone who bought gifts there will now drive about ten minutes north.

The rest stayed close. Wind in the Willows kept its building and moved its door to a side street. Aldo Castillo's gallery stays on the avenue. He told Gulfshore Business he found the 472 Fifth Ave. S. space three weeks before he had to leave the old one. His new space opens Sunday, Nov. 1. East-West Sports Cards is moving a few blocks along the same street.

Besides Regatta, two names leave the street entirely. Silver Eagle Gallery, a Native American jewelry and accessories store whose building M Development doesn't own, has moved away. The report gives no new address. L'Olivo, the trattoria at 651, is the other, and its story is covered further down.

Why the Ground Floors Are Changing Hands

This is the street's third makeover. The first started in 1994, when the city hired the planners Andrés Duany and Elizabeth Plater-Zyberk and created a redevelopment area covering Fifth Avenue South. That effort brought the Sugden Community Theatre, what is now the Naples Art Institute, and several parking garages. The second began in 2015, when Hoffmann Commercial Real Estate started buying buildings and added its sculptures. In 2023 the company sold about 27 Naples addresses, more than a dozen of them downtown, to M Development, a firm based in Aspen, Colorado.

That sale is behind this year's moves. Derek Nagy, M Development's Naples property manager, explained the plan 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 company's "big push is soft retail, as opposed to office," with more retail planned for first floors.

That's why the new names are mostly clothing stores. Spartina 449, a women's wear brand, took half of Regatta's old space. Faherty, which sells upscale clothing, takes the Wind in the Willows corner. Johnnie-O, a casual menswear brand, is another store the company brought in. Johnnie-O's store page lists its Naples shop as open at 375 Fifth Ave. S., Monday through Saturday 11 a.m. to 7 p.m. and Sunday noon to 6 p.m.

Not every new tenant sells clothing, though. East-West Sports Cards is moving trading cards into a space that used to hold bronze sculpture. Tiny Kitchen Empanadas opened in the same building with a walk-up business. Small independent shops are still opening on these ground floors, even as larger spaces get split up for national clothing brands.

The Block That's Dark for a Different Reason

The stretch residents ask about most is the two-story building at 649–663 Fifth Ave. S. It sits on the north side of the street, just west of Inn on Fifth, and has been gutted since summer 2025 while its redevelopment waits on a city building permit.

According to Gulfshore Business, restaurateur Feibi Gouda and her family closed L'Olivo at 651 before the interior was demolished. They plan to replace it with Riva Mediterranean Restaurant & Lounge, plus Zanu Sushi Bar next door in Roma pizzeria's old space. The family has run restaurants in the area for 25 years. Before L'Olivo, which ran for more than six years, the same space held their South Ave Restaurant and Crispy Seafood & Wine Bar.

The publication reports that the city reviewed the 60-year-old building as new construction, so the work had to meet the current building code. That review brought questions about floodproofing and soil, plus a stormwater review. Gouda said the restaurant permits themselves had all been approved. She hoped to have the building permit by the end of October and estimated six to eight months of work after that, which puts the opening after the 2027 season. "We're losing the second season," she said. The family had planned to open in early 2026.

Nagy, speaking to the same outlet, told L'Olivo's regulars that "they're coming back, and they'll have several other concepts, as well." So the boarded-up block near Park Street will most likely stay boarded up for all of this winter.

Evenings to Walk the New Mix

The easiest time to see the changes is on nights when the city and the merchants put music on the sidewalks. Here's the calendar from Halloween through mid-November, from the 5th Avenue South events calendar and the presenters:

1. Saturday, Oct. 31, 3 to 5 p.m.: The 5th Avenue South Halloween Spooktacular at Cambier Park, with live music, a costume contest and games.
2. Saturday, Oct. 31, 5 to 8 p.m.: A special Evening on Fifth right after the Spooktacular, with musicians along the sidewalks. It's the first chance to walk past the Faherty corner and the Wind in the Willows side door after dark.
3. Sunday, Nov. 1, 2 to 3 p.m.: The Naples Concert Band opens its 55th-anniversary season with "Italian Masterpieces and American Pride" at Cambier Park, featuring vocalist Jeanie Darnell. It's the same day Aldo Castillo's gallery starts at 472 Fifth Ave. S.
4. Monday, Nov. 9, 7 to 9 p.m.: The Stardust Memories Big Band at the Cambier Park bandshell.
5. Thursday, Nov. 12, 6:30 to 9:30 p.m.: The first regular Evening on Fifth of the season. The calendar lists more on Dec. 10, Jan. 14, Feb. 11 and Mar. 11.
6. Friday and Saturday, Nov. 13–14: Gifted!, a pop-up holiday market at the historic Naples Woman's Club just off Fifth Avenue, raises money for student scholarships.
7. Sunday, Nov. 15, 2 to 4 p.m.: The Naples Big Band starts its free six-concert Cambier Park series, which runs through April 11, 2027.

On Halloween night, a good walking loop starts at the Cambier Park bandshell and heads east past 630 and 675. Then turn back west toward 472 and Bar Tulia, and you'll have passed most of the old and new addresses in the table.

Fifth Avenue South affects property values downtown as much as it shapes residents' evenings. Our team watches who's signing leases on the street as closely as we watch closed sales. If you live near the avenue and want to know how this season's tenant changes could affect your home's value, Dominick Clarizio and the Dom and Judie Team can walk through it with you. Get your instant home valuation or schedule a free consultation.