On Fifth Avenue South, the Independents Are Moving Sideways

Mid-afternoon at Tiny Kitchen Empanadas, a vintage turntable plays 33 1/3 records while beef, chicken, spinach-ricotta, ham-and-cheese and mushroom empanadas come out of the oven at a steady pace. Owner Alejandro Vega told Naples Press that he has run the business in various locations for 15 years. This summer it opened around the corner from Fifth Avenue South, at 524 Park St., the address Florida Weekly gives for the shop.

That address says more about this season's downtown than any single opening. Fifth Avenue is changing hands again, and the independent businesses that gave it character are mostly staying downtown. They are moving down the block, around the corner, or to a side door, and the central ground-floor storefronts are going to national apparel brands. If a regular stop seems to have vanished, it has probably moved a few hundred feet.

Who Owns the Storefronts

The current reshuffle started with a sale. Hoffmann Commercial Real Estate began buying downtown buildings in 2015. In 2023 the company, then run by David Hoffmann's sons Greg and Geoff, sold about 27 of its Naples addresses, more than a dozen of them downtown, to Aspen, Colorado-based M Development. Its property arm is NECO.

This is the avenue's third reinvention. The first came in 1994, when the city hired urban planners Andrés Duany and Elizabeth Plater-Zyberk and set up a redevelopment district that produced the Sugden Community Theatre, what is now the Naples Art Institute, and several parking garages.

M Development has been open about what it wants. "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 company's Naples property manager, told Naples Press. "The big push is soft retail, as opposed to office. We're trying to put a lot of retail on the first floor now."

Rents are moving with the strategy. Aldo Castillo told the same paper that he paid $16,000 a month for his 1,750-square-foot gallery at 634 Fifth Ave. S. His renewal would have cost between $32,000 and $35,000, because the landlord said another tenant would pay that much. At roughly double the old rent, the prime ground floors suit tenants with national sales behind them. The local businesses reorganize around them.

The Sideways Map

Here is where familiar names have gone, according to Naples Press reporting from mid-October.

Three of the four moves stayed downtown, and all three stayed in the same building or on the same street. Wind in the Willows, known on the avenue for its porcelain, script-titled facade, kept its address by moving its entrance to a side street. The Castillo gallery, known for pieces like Ancizar Marin's fiberglass "Pollock Climbers," will reopen there on Nov. 1.

Regatta went farthest. The gift shop had been downtown since 1985, and co-owner Vaida Gard told Naples Press, "Our lease was not renewed." Its one-of-a-kind gifts are now at Vanderbilt Beach Road and U.S. 41 North. That puts Regatta in roughly the same northern retail corridor M Development hopes to draw shoppers back from.

Some departures were not about the landlord. Silver Eagle Gallery, a Native American jewelry and accessories store in a building M Development does not own, also left. Sushi-Thai, in the rotunda building at the Four Corners of U.S. 41 and Fifth Avenue South, closed in June 2024. Its owners said at the time that the decision was theirs alone and that they wanted to focus on their other area restaurants.

What Fills the Center Blocks

The incoming tenants show the price point. Faherty, announced for the old Wind in the Willows corner, sells men's shirts that mostly start at $150. Johnnie-O, a casual menswear brand M Development brought in, starts casual shirts at about $158. Spartina 449, a women's wear company store, will share the divided Regatta space with a flip-flop boutique. These are announced tenants, so check the storefront before planning a trip around one.

Nagy said splitting large spaces is deliberate, with the goal of putting "more retail" on the street "because that's going to drive overall activity and foot traffic on the avenue." More storefronts from the same square footage means more doors along a single block.

Lunch Moved to the Edges

The restaurants that opened downtown this year follow the same pattern. They are casual, and half of them sit just off the avenue itself. Naples Press covered two of them in March.

• All Too Well Gourmet Sandwiches, 795 Fifth Ave. S., opened Feb. 12. Owner and chef Mitchell Jamra makes 11 sandwiches on Tuscan schiacciata, including Italian beef, pork, turkey, Buffalo chicken and tuna.
• Barrio Taqueria, 539 Fifth Ave. S., opened Feb. 18. Owner Sal Muñoz serves tacos, empanadas, quesadillas, salad, sides, beer, wine and agua fresca.
• Tiny Kitchen Empanadas, 524 Park St., opened this summer in the same building complex as Castillo's old gallery and was doing brisk walk-in business by fall. "We're a month away from season, so I'm really excited," Vega told Naples Press.
• Annie's Bistro, Bar & Bakery opened May 15 inside the new Olde Naples Hotel at 200 Broad Ave. S., a Camalier family and Ocean Properties venture. Naples Press reported that it serves breakfast, lunch, dinner and cocktails, with espresso, house-made pastries and an approachable American menu in the evening.

Annie's is on Broad Avenue South and Tiny Kitchen is on Park Street, both a short walk from Fifth. All Too Well and Barrio sit on the 700 and 500 blocks, while the brand tenants named so far are going into addresses such as 651, 675 and 760.

The Gutted Building Near Park Street

The longest gap on the street is at 649-663 Fifth Ave. S., on the north side, just west of Inn on Fifth. That M Development building held L'Olivo and Roma pizzeria. Its interior was gutted in summer 2025, and it has been in limbo for more than a year.

The holdup is a code question. Gulfshore Business reported that the City of Naples treated the redevelopment of the 60-year-old building as new construction, so the whole building had to meet the current code. The city questioned the structural engineer's dry-floodproofing analysis, and the developer had to hire a geologist for soil borings to satisfy geological and FEMA requirements. A May 7 corrections letter from the city's stormwater review asked for total reconstructed square footage across both permits to decide whether the project crossed the city's 50 percent redevelopment threshold.

Restaurateur Feibi Gouda and her family ran L'Olivo for more than six years in a space where they had earlier owned South Ave Restaurant and Crispy Seafood & Wine Bar. They are coming back with new concepts. Riva Mediterranean Restaurant & Lounge is planned for 651 Fifth Ave. S., with Zanu Sushi Bar next door in the former Roma space. Nagy also told Naples Press that the L'Olivo team is "coming back, and they'll have several other concepts, as well."

Gouda hoped to have the building permit by the end of October. She estimates six to eight months from permit to opening, which points to a post-season 2027 launch, Gulfshore Business reported. The original plan was to open in early 2026. The city's Design Review Board still has to approve the facade changes, though interior work can begin first, and second-floor tenants have not been announced.

Dates on the Avenue Before Thanksgiving

The street's own calendar has several fixed dates coming up, according to the Fifth Avenue South events calendar.

1. Oct. 31, 3 to 5 p.m. Halloween Spooktacular at Cambier Park and Park Street, the same street as Tiny Kitchen.
2. Oct. 31, 5 to 8 p.m. A special Halloween Evening on Fifth along the avenue.
3. Nov. 1. Aldo Castillo Gallery opens at 472 Fifth Ave. S., next to Bar Tulia.
4. Nov. 12, 6:30 to 9:30 p.m. The next regular Evening on Fifth.

The Halloween afternoon and Nov. 12 are good chances to walk the length of the avenue and see the new layout. Wind in the Willows is around the side of 675, the gallery is at 472 near Bar Tulia, and the newer lunch spots run from Park Street to Broad.

Fifth Avenue's tenant changes also shape how downtown Naples feels to the people who own homes nearby. If you are weighing a residence within walking distance of Fifth or Third Street South and want a frank, current read on how these changes affect daily life there, Angelica Andrews would be glad to walk the blocks with you. Request a Private Consultation.