Where Your Fifth Avenue South Regulars Went This Fall

"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," Derek Nagy, the Naples property manager for M Development, told the Naples Press this month. He described the plan this way: "The big push is soft retail, as opposed to office. We're trying to put a lot of retail on the first floor now."

That plan explains most of what changed on the Avenue this fall. Ground-floor space is being re-leased to retail tenants, so some familiar names have given up a storefront without leaving downtown. Wind in the Willows now uses a side door, Aldo Castillo's gallery is moving a few blocks down the street, a new empanada shop opened on a side street just off the Avenue, and Regatta went north to a shopping center on U.S. 41. You can still reach almost all of them on foot or with a short drive.

The Avenue's Third Makeover

Fifth Avenue South has been rebuilt on purpose before. In 1994 the city hired the urban planners Andrés Duany and Elizabeth Plater-Zyberk and set up a redevelopment district that covered the street. That effort produced the Sugden Community Theatre, the space that is now the Naples Art Institute, and several parking garages. It also swapped practical shops like the old camera store for boutiques, galleries and restaurants.

The second change began in 2015, when Hoffmann Commercial Real Estate started buying downtown buildings and brought in the whimsical statues that now show up in so many visitors' photos. In 2023 the company sold about 27 of its Naples addresses, more than a dozen of them downtown, to M Development, which is based in Aspen, Colorado. The Naples Press reports that HF Companies still owns buildings on the Avenue as well.

So this fall is the third time in about thirty years that the people who own the buildings have redrawn the Avenue's tenant mix. The 1994 makeover pushed out practical shops. This one is moving longtime tenants off prime corners and filling the bigger ground-floor spaces with retail.

A Map of Where Everyone Went

Here are the moves reported by the Naples Press and Gulfshore Business on Oct. 16, 2026, showing where each business was and where it is now, including one restaurant that has paused rather than moved.

Wind in the Willows moved the shortest distance. The clothier is known for its porcelain facade with script lettering, and after the building sold it kept its downtown address by moving to a side-street entrance in the same 675 Fifth Ave. S. building. If you used to walk in from the corner, the store is still in the same building, just through a different door.

Regatta moved the farthest. The gift shop had been downtown since 1985 and is now at The Marketplace at Pelican Bay, at Vanderbilt Beach Road and U.S. 41 North. If you live in North Naples, it may now be closer to home than it was before.

What Fills a Large Ground Floor

The new tenants on the Avenue show how Nagy's plan works in practice. He told the Naples Press that the company is focusing on larger spaces, and Regatta's old store at 760 Fifth shows what that means. It was split in two. One half is a flip-flop boutique and the other is Spartina 449, a women's wear company store. Spartina's own Naples store page lists the shop at 760 Fifth Avenue South, along with its hours.

A few more retail names are part of the same effort:

• Johnnie-O, a casual menswear brand, is one of the retailers Nagy says the company has brought onto the Avenue.
• Faherty, an upscale clothing brand, is slated for the corner of the 675 building that Wind in the Willows used to occupy.
• East-West Sports Cards & Collectibles will sell small collectibles rather than clothing in Castillo's old gallery space.

"[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 told the Naples Press. The reasoning is simple. Shops that face the street bring people in on foot, and offices on the first floor don't.

The Gallery That Moved Down the Street

Aldo Castillo's move shows how a business can stay on the Avenue without keeping its old address. Castillo, who was born in Nicaragua, ran a gallery at Miromar Design Center in Estero for 17 years. Over the last seven years he built up a second gallery in a 1,750-square-foot space at 634 Fifth Ave. S., and in 2025 he combined both into the Fifth Avenue location. His new space at 472 Fifth Ave. S., next to Bar Tulia, is still on the Avenue.

He told the Naples Press that he likes foot traffic even when the people walking in aren't buyers, and he called Fifth Avenue South the perfect location for that. His collection includes stone sculptures, lightbox paintings and Ancizar Marin's "Pollock Climbers," fiberglass figures climbing their own ropes. All of it will be at the new address starting Nov. 1.

Some shops have left the Avenue completely. Silver Eagle Gallery, which sold Native American jewelry and accessories from a building M Development doesn't own, has moved away. The report didn't say where.

New Spots on a Side Street and a Rooftop

Not every recent opening is on a ground floor facing the Avenue. Tiny Kitchen Empanadas opened this summer, and Florida Weekly lists it at 524 Park Street, just off Fifth Avenue South. The owner has run the business at different locations for 15 years, according to the Naples Press. He plays 33 1/3 records on a vintage turntable and bakes beef, chicken, spinach-ricotta, ham-and-cheese and mushroom empanadas, and when the Naples Press visited, walk-in business was steady even in mid-afternoon. "We're a month away from season, so I'm really excited," he told the paper.

Another new spot is on a roof. Prime Social Reserve is a rooftop restaurant at 837 Fifth Ave. S. Its website now shows guests dining, describes VIP access to the restaurant, and says its access plans are full, with a waitlist. Earlier coverage in the Naples Press described it as reservation-only.

L'Olivo Is Coming Back

L'Olivo is the one people ask about most. The trattoria at 651 Fifth Ave. S. closed while M Development renovates the building's facade, and the work has been held up by permitting differences with the city. Nagy told the Naples Press that the restaurant will reopen. "They're coming back, and they'll have several other concepts, as well," he said. No reopening date has been given. Until there is one, the 651 building is the one to keep an eye on.

Dates That Bring You Back to the Avenue

The season's events are a good chance to see the new layout in person. Cambier Park, a block off the Avenue, and the Avenue itself have these dates on the calendar:

1. Nov. 14: Fine Arts & Craft Show at Cambier Park, 10 a.m. to 4 p.m.
2. Nov. 28: Art in the Park at Cambier Park, 10 a.m. to 4 p.m.
3. Dec. 4–5: The Fifth Avenue South Christmas Walk runs 5 to 10 p.m. Friday, with the tree lighting expected around 6 p.m., and 10 a.m. to 10 p.m. Saturday.
4. Dec. 8: The City of Naples Christmas Parade starts at 6:30 p.m. at Third Street South and Ninth Avenue South, heads up Fifth Avenue South and ends at City Hall.

The Christmas Walk is a good time to try the new route. Go in the side entrance at 675, walk down to 472 to see Castillo's new gallery, and stop for empanadas on Park Street.

If you're thinking about a home within walking distance of Fifth Avenue South, or you want to know what the Avenue's changing tenant mix could mean for a property you already own downtown, Kyle R. Suhr walks these blocks regularly and is glad to talk it through. Discover Your Gulf Coast Lifestyle — Contact Kyle.