Where Fifth Avenue South's Familiar Shops Landed This Season

Walk the 600 block of Fifth Avenue South this week and the changes show up at street level. The porcelain facade of Wind in the Willows, the corner shop with the script lettering, now greets you from the side of its building. The front door at 634 no longer opens onto Aldo Castillo's lightbox paintings and fiberglass climbers. Farther east, 760 Fifth, which was Regatta for decades, has been split into two storefronts. On a first lap of the season it can look as if the old avenue is emptying out.

Most of it moved rather than closed. The gallery, the clothier, the gift shop and the Native American jewelry store that left their old addresses over the past few seasons are almost all still open in Naples. Some went a few doors down, one went around the corner of its own building, and two went north toward Pelican Bay and Seagate. If you know where they went, the avenue makes more sense this winter, and it's easier to read what is moving into the spaces they left.

Why so many front doors changed

The reshuffle has one main source. Naples Press reported that in 2023 Hoffmann Commercial Real Estate sold about 27 Naples addresses, more than a dozen of them downtown, to Aspen-based M Development. Leases have since come up for renewal on the new owner's terms, building by building.

The company's plan for those buildings is plain. "The big push is soft retail, as opposed to office. We're trying to put a lot of retail on the first floor now," Derek Nagy, M Development's Naples property manager, told Naples Press. He said the goal is to bring back retailers who have been choosing Mercato. The company has focused on larger spaces and divided some of them. Under that plan, a gallery or a gift shop that has occupied a big ground-floor room for years becomes a candidate for a move.

This isn't the avenue's first remake. The same Naples Press piece traces a 1994 city-led redesign by urban planners Andrés Duany and Elizabeth Plater-Zyberk. That project brought in Sugden Community Theatre, what is now the Naples Art Institute, and the parking garages, and it replaced utilitarian shops such as the old camera store with boutiques, galleries and restaurants.

The block-by-block map

Here is where the familiar names went and who is in, or headed into, the spaces they left.

The table shows a chain of moves. The sports card shop leaving 785 opened that suite to State & Liberty Clothing Co. It is taking over the gallery space at 634, which opened up when Castillo took a new address at the west end of the avenue near Bar Tulia. A single lease change set off three moves along the same street.

Castillo's move also shifts the art. Naples Press reported that the gallery's narrative, process-driven work would be showing from the new space starting Nov. 1. If a visit to Fifth usually ends at the gallery, from November on it ends farther west.

There is new food in the 600 block too. Tiny Kitchen Empanadas opened this summer in the same building as Castillo's former gallery. Owner Alejandro Vega plays records on a vintage turntable and bakes beef, chicken, spinach-ricotta, ham-and-cheese and mushroom empanadas through the afternoon. "We're a month away from season, so I'm really excited," he told Naples Press.

The two that left the avenue entirely

Two longtime names went farther than a few doors.

Regatta, the "fun things for fun people" gift shop, moved north after about 40 years downtown, Gulfshore Business reported. It now fills a Marketplace at Pelican Bay space that New Balance vacated, at Vanderbilt Beach Road and U.S. 41, and it still carries nautical pieces, home accents, resort wear and gifts. For North Naples residents, the shop that used to mean parking downtown is now a stop on the way home.

Silver Eagle Gallery, the Native American jewelry and accessories store, moved out of its Fifth Avenue building, which M Development did not own. Its new location at 780 Seagate Drive is open, according to the gallery's own site.

So the old Fifth Avenue errand route now ends partway up Tamiami Trail. Both moves put the stores closer to the Pelican Bay corridor, which already draws residents for other reasons.

What's arriving on the ground floors

The newcomers fit the retail-first plan Nagy described. Naples Press reported that Regatta's old space at 760 was split into Spartina 449, a women's wear company store, and a flip-flop boutique, and that Johnnie-O, a casual menswear label, has joined the avenue. Faherty is slated for the Wind in the Willows corner at 675, but no opening date has been posted. State & Liberty Clothing Co., a Michigan-based brand, opened Oct. 12 at 785 Fifth Ave. S.

The local business district is watching the balance. "Growth is important, but so are authenticity, local character and the mix of businesses that our residents and visitors have come to value," Meg Stepanian, executive director of the Fifth Avenue South Business Improvement District, told Naples Press. She noted that the avenue has "never been static."

Two dining rooms near Four Corners

On the east end, the restaurant story is about which tables are open and which are still waiting.

La Trattoria, at 878 Fifth Ave. S. near Four Corners, is the steady one. After a three-month closure for ceiling repairs, it came back with the same yellow awnings, red-checkered tablecloths and 40-person staff, according to Naples Press. The menu stayed the same, with an updated cocktail list and wine list and a new piece of kitchen equipment behind the pizza, pasta and bread. "We closed, we fixed all of the problems and we're back stronger than before," managing partner Massimiliano Tonni told the paper. Naples Press listed its hours as 4 p.m. to 1:30 a.m., Tuesday through Sunday.

L'Olivo, the trattoria at 651 Fifth Ave. S., is still closed while M Development upgrades the building's facade, a project held up by permitting with the city. Nagy told Naples Press the restaurant will return: "They're coming back, and they'll have several other concepts, as well." No reopening date has been announced. For now, La Trattoria anchors the Italian end of the street alone.

When to walk it

The new map is easiest to learn on the evenings the avenue is set up for strolling. Here are the season's dates on and around Fifth:

1. Evening on Fifth, Thursday, Nov. 12, 6:30 to 9:30 p.m. Sidewalk live music with dining and shopping along the avenue, per the Fifth Avenue South events calendar. It's the first good chance to see State & Liberty, the 600 block and Castillo's new address in one walk.
2. Annual 5th Avenue South Christmas Walk and Tree Lighting, Dec. 4 to 5. The program includes a Sugden Plaza tree lighting, a living nativity, a skating rink, live music, Santa and avenue dining, according to the event listing.
3. City of Naples Christmas Parade, Tuesday, Dec. 8, 6:30 p.m. The route starts at Third Street South and Ninth Avenue South, runs up Fifth Avenue South and ends at City Hall on Eighth Street South, per the City of Naples.
4. Evening on Fifth, Thursday, Dec. 10, 6:30 to 9:30 p.m. The second date on the business district's calendar, with Faherty's corner and L'Olivo's facade worth checking again.

For the gift shopping that used to happen at 760 Fifth, Regatta's Pelican Bay shop is open on the same nights, about a 15-minute drive north. Silver Eagle is on Seagate Drive.

If you have a favorite shop on the old Fifth Avenue route and want to know where it fits on the new one, or you want to compare notes on how the avenue's changes are playing out across downtown Naples, Nita Rapp follows this street closely and is glad to talk it through. Let's Connect.