Walk east on Fifth Avenue South around six on a Thursday and you'll see it happen in real time. Near Fourth Street, valets are already circling with claim tickets, waiting for the dinner rush at Del Mar and Osteria Tulia. Three blocks down, past Eighth Street South, someone is eating a birria taco standing up at a counter, no reservation required, no jacket expected. Same avenue. Same zip code. Two completely different nights out.
That split is new. It didn't exist five years ago, and it isn't an accident. It's the result of a specific run of openings over the past year that quietly gave Fifth Avenue South a second identity to go with its old one, and if you live in Port Royal and treat this street as your default answer to "where should we eat," it's worth knowing which half you're actually walking into before you leave the house.
Two Streets Wearing One Name
For most of its history, Fifth Avenue South has run on one register: white tablecloths, a wine list that requires a second look, and a bill that assumes you're celebrating something. That version is still there and still expanding. But the stretch toward Eighth Street South has filled in behind it with something the avenue hasn't had before: counter-service spots where a meal for two costs less than a single entree at the places three blocks west.
The storefronts themselves tell the story. All Too Well Gourmet Sandwiches took over a retail unit on the corner of Fifth and Eighth that used to be the Toad Hall extension of the adjacent Wind in the Willows boutique, a longtime art and antique shop. Barrio Taqueria moved into a space next to Grace & Shelly's that was a longtime real estate office before it most recently became a Pack & Post shipping outlet. These weren't restaurant spaces waiting for a restaurant. They were ordinary downtown storefronts that a wave of newer, smaller operators decided were worth converting, at a scale and price point that didn't used to pencil out on this particular block.
Meg Stepanian, executive director of the Fifth Avenue South Business Improvement District, has described it as part of the strip's "thoughtful evolution," and the phrase fits better than most marketing language does. This isn't a strip losing its identity to fast-casual. It's a strip that added a second gear.
Here's what actually changed hands this year, and what used to be there:
- All Too Well Gourmet Sandwiches, 795 Fifth Ave S, corner of Eighth Street South. Opened February 12 in a former Toad Hall retail annex. Chef Mitchell Jamra runs it as an offshoot of his Chicago sandwich shop, built on curated deli meats and schiacciata bread.
- Barrio Taqueria, 539 Fifth Ave S. Opened this past February in a space that was most recently a Pack & Post shipping outlet and a real estate office before that. Owner Sal Muñoz, who also runs Unidos on Central Avenue, built the menu around birria tacos and esquites.
- Bontà Bakery, 824 Fifth Ave S. Launched two years ago and is still the go-to for a coffee and pastry stop before a walk.
- Slice Shop, 720 Fifth Ave S. A by-the-slice pizza counter that opened last year, filling a gap the avenue genuinely didn't have before.
- Tiny Kitchen Empanadas, a few steps off Fifth Avenue South. Run by three generations of the same family, it grew directly out of their farmers market stand, formerly known as CDL Empanadas.
None of these required a reservation when this piece was written. That alone is a change worth noting on a street where reservations used to be the default assumption.
The Top Tier Isn't Slowing Down
None of this means the formal end of the avenue is fading. If anything, the past year has been one of the busier stretches for high-end openings Fifth Avenue South has seen in a while.
Le Colonial opened at 457 Fifth Ave S last December, a French-Vietnamese room from restaurateurs Rick Wahlstedt and Joe King built around the flavors of 1920s Saigon. The same weekend, Limón opened its rooftop seven blocks east at the corner of Fifth and Goodlette-Frank, on top of the new AC Hotel Naples 5th Avenue by Marriott. Del Mar Naples, from Cameron Mitchell Restaurants, took over the old Café Lurcat space with two floors of dining and a private room that seats two dozen.
The next major arrival is already approved and under construction. Stefano Frittella, the restaurateur behind Bice, Caffe Milano, La Trattoria and Vergina, all on this same avenue, won design review approval for a new concept called Avenue 31, slated to sit between Del Mar and Osteria Tulia at 472 Fifth Ave S. It's named for the address of his restaurant in Monte Carlo, and it's the kind of project that only gets built by someone who already knows the avenue's top end can support a fifth restaurant from the same owner. The space was still working through buildout as of the most recent public filings, so it isn't open yet, but it's a clear signal that the formal side of the street isn't ceding ground to the counter-service side. It's building next to it.
A few blocks over at Naples Bayfront, Ce Soir is part of the same wave, a French-inspired room from Canadian hospitality group Aiden Hospitality making its U.S. debut. It's not technically on Fifth Avenue South, but it's close enough that it's part of the same evening for most people walking that stretch of downtown.
"We're seeing the thoughtful evolution of Naples' iconic Fifth Avenue South," Stepanian said, describing an avenue that's adding more accessible options without losing its high-end anchors.
Picking Your Register
If you're deciding where to point the car, or more likely where to park it once and walk, here's how the current lineup breaks down by what kind of night you're actually having:
| If tonight is... | Go to | Where | What you're getting |
|---|---|---|---|
| A fast weeknight dinner | Barrio Taqueria | 539 Fifth Ave S | Birria tacos, esquites, no reservation |
| A sandwich and a walk | All Too Well | Corner of 5th & 8th St S | Chicago-style sandwiches on schiacciata |
| Coffee before the beach | Bontà Bakery | 824 Fifth Ave S | Pastries and espresso, grab and go |
| A slice between errands | Slice Shop | 720 Fifth Ave S | By-the-slice pizza, standing counter |
| A proper occasion | Le Colonial | 457 Fifth Ave S | French-Vietnamese, dressed-up room |
| Sunset with a view | Limón | Rooftop, Fifth Ave S & Goodlette-Frank | Rooftop cocktails atop the AC Hotel |
| A long dinner with wine | Del Mar Naples | Former Café Lurcat space | Mediterranean coastal, private dining available |
That table didn't exist a year ago, at least not with this many rows on the casual side. The old version of Fifth Avenue South only had answers for the bottom three rows.
What This Changes for a Tuesday
None of this is a reason to move, sell, or reconsider anything about where you live. It's simpler than that. Port Royal sits close enough to downtown that Fifth Avenue South has always been the easy answer to "where should we go tonight," and for a long time that answer came with a certain amount of friction: dressing for it, booking ahead, spending accordingly. That friction is gone for half the street now. You can decide, on the way out the door, whether tonight is a birria taco night or a Le Colonial night, and both options are on the same six blocks.
That's the kind of small, specific shift that doesn't show up in a listing description or a market report, but it's the kind of thing that actually changes how a neighborhood feels to live in. Josh Greenwald pays attention to these details because they're part of what makes Port Royal worth the drive downtown in the first place, not because they sell houses. If you're weighing a move to this stretch of Naples and want a read on the neighborhood that goes beyond square footage, Josh Greenwald is worth a conversation.
