If you have lived in Naples for more than a couple of seasons, you have a mental map of dining anchors: the place at Waterside that never needed a reservation, the ice cream counter you walked to after dinner, the chain on Tamiami Trail that had been there since your kids were small. In the first half of 2026, most of that map got redrawn. The story is not that Naples lost restaurants. The story is what replaced them, and how much more ambitious the replacements are.
This is a post for people who already eat here. Consider it a quick tour of where the tectonic plates moved between January and now, and why summer is the right window to actually try what is new.
The Closings Are Bigger Than They Look
The reason the map feels different is that several of the losses were multi-decade fixtures, not new concepts that failed to catch on. Recent Waterside Shops departures include CAVO Lounge at Mercato after 11 years, Skyline Chili in Naples and Fort Myers after 38 years, Brio Italian Grille at Waterside after 20 years, Häagen-Dazs at Waterside after 25 years, and Kunjani Craft Coffee & Gallery on Seagate Drive after 10 years.
| Restaurant | Location | Years in market |
|---|---|---|
| Brio Italian Grille | Waterside Shops | 20 |
| Häagen-Dazs | Waterside Shops | 25 |
| Skyline Chili | Naples & Fort Myers | 38 |
| CAVO Lounge | Mercato | 11 |
| Kunjani Craft Coffee | Seagate Drive | 10 |
The point is not the individual losses. The point is the cluster. Longtime franchises of Skyline Chili in Naples and Fort Myers both closed in April, and other longtimers closing included Sonic Drive-In in East Naples and Brio Italian Grille and Haagen-Dazs at Waterside Shops. When five anchors go in one two-quarter window, the dining pattern of an entire cohort of residents has to rebuild itself around new coordinates.
Tamiami Trail Is the New Center of Gravity
If Fifth Avenue South is where Naples spends its money in season, the two-mile stretch of Tamiami Trail North between Neapolitan Way and The Pavilion has quietly become where the interesting cooking is happening.
The headline opening is Heyday Cookshop. Heyday launched in the Neapolitan Way restaurant space that used to be home to Ziggy D'Amico's Whiskey Bar & Diner and D'Amico & Sons for many years, as a second restaurant from Kayla Pfeiffer, the acclaimed executive chef and founding partner at Bicyclette Cookshop in North Naples, promising New American cuisine with a rotation of top national chefs in residency amplified by a hi-fi listening room. Pfeiffer is not an unknown quantity here. When her North Naples restaurant, Bicyclette Cookshop, debuted in 2023, Gulfshore Life rewrote its Best New Restaurants feature at the last minute to include it, and the James Beard Foundation named her a semifinalist for its Emerging Chef award.
The chef residency piece is the part worth paying attention to as a resident, because it means the menu you eat in July is not the menu you eat in September. Heyday introduced Southwest Florida's first chef residency program, hosting visiting chefs for extended collaborations, and the inaugural lineup included Jorge Pabon, former executive chef of Michelin-starred Estela in New York City, followed by chef Isaac Villaverde, whose Panama City restaurant La Tapa Del Coco champions Afro-Panamanian culinary heritage.
A short walk up the same corridor, the pattern repeats at a very different price point. Claypot Turkish Restaurant opened at 4910 Tamiami Trail N. in late May as a fast-casual Turkish concept where everything is made from scratch in actual clay pots, comparable to Cava or Chipotle but Turkish, with a Mini Grand Bazaar of imported Turkish goods inside.
The Tamiami corridor also picked up serious fine-dining depth. At Amber Cove, familiar Gulf standards like grouper, sea bass and short ribs feel reinvented under former Baleen chef Jehad Alsharabini, who tinkers with formal technique and creative pairings at a level only seen at a shortlist of the region's top restaurants. Farther north, ChaChaCha Fusion Cuban restaurant opened in February at The Strand retail center in North Naples.
If you tried to eat at Bicyclette in February, you know the calculus. In August, the calculus is different. Walk-in seats exist. Reservations open up two days out. The chef is in the kitchen instead of in the weeds.
Waterside Shops Is Rebuilding Its Roster With Two Big Bets
Losing Brio and Häagen-Dazs in the same year could have left Waterside looking hollow. The mall's response is not to replace them in kind. It is to trade a family-casual anchor and a walk-up ice cream counter for two of the most-watched restaurant openings on either coast of Florida.
Buck & Rider is targeting a late 2026 opening at Waterside Shops, featuring an open kitchen, expansive raw bar, and breezy indoor-outdoor seating, with CEO Adam Strecker describing Naples as a natural first choice for the brand's first expansion outside Arizona. The second bet is bigger. RH Restaurant, also targeting late 2026, will be the fine-dining restaurant at the center of Restoration Hardware's new glass-atrium gallery on the former Nordstrom site, and given how RH restaurants have become destinations in their own right at other locations, the Naples version will be one of the most anticipated openings of the year when it arrives.
Read that as a signal about what Waterside thinks its shopper wants for the next decade. It is not another mall-food-court expansion. It is a decision to compete with Third Street South and Fifth Avenue for the evening.
Fifth Avenue, Mercato, and the Naples Bay Resort Additions
Downtown did not sit still either. Chef Vincenzo Betulia debuted an haute steakhouse on Fifth Avenue South with an impressive Wagyu program and blue-chip wine list, and the Naples Beach Club, A Four Seasons Resort, opened reservations for its flagship restaurant helmed by two-time James Beard Award winner Gavin Kaysen. Betulia is the operator behind Osteria Tulia and Bar Tulia. Kaysen is the Minneapolis chef behind Spoon and Stable. Neither is testing the water. Both are here.
Mercato is filling its CAVO-shaped hole with a taverna. Grilled lamb chops, branzino, and Greek-inspired cocktails headline Violí's taverna-style menu coming soon to the Mercato. And on the water, Blackbird Modern Asian will open its second location inside Naples Bay Resort with immersive décor and waterfront views.
There is also a retail piece worth flagging for anyone who hosts. The Good Pour is opening in 2026 as a large-format marketplace for wine, spirits, and craft beer, mixing well-known labels with new discoveries, with a give-back model where a portion of each purchase is directed to a charity you choose through The Good Pour app.
Why Summer Is When Residents Actually Get to Use This
The subtext of every one of these openings is that the operators need summer traffic to survive. Recent months of conversations with chefs and restaurateurs revealed an industry under pressure, with rents and operating costs sky high and the summer months exceptionally slow. That pressure is your leverage as a resident.
Summer in Naples gets a bad reputation from people who have never stayed through one; the crowds thin, the parking gets easy, and the restaurants that stay open start doing things for locals they would never do in January. Chops City Grill is running 25 percent off entrees and steaks through the summer. Third Street South rooms that require weeks of advance notice in February are taking walk-ins on a Tuesday in July.
There is one more piece of context that matters for how residents spend evenings this summer, and it is not a restaurant. On March 4, 2026, the Naples City Council unanimously approved the final design for the Naples Pier reconstruction, a $26.3 million project representing the seventh reconstruction of the 137-year-old historic pier at the west end of 12th Avenue South. A groundbreaking ceremony in January 2026 marked the official start of reconstruction. With the pier closed to walking traffic and FEMA guidelines prohibiting permanent structures like the former Cosmos at the Pier from being built over water, the City Council opted for a portable concession cart instead of permanent indoor dining.
Translation for residents: the sunset walk that used to end in a pier concession now ends on Fifth Avenue or Third Street South. The pier being offline is quietly redirecting foot traffic downtown for at least the next construction cycle, and the restaurants opening this year are the ones catching it.
What This Adds Up To
The single-sentence version: Naples in 2026 is trading breadth for depth. Fewer everyday chain anchors, more chef-driven rooms with real ambition. The Waterside redevelopment, the Tamiami Trail cluster around Heyday and Amber Cove, and the Fifth Avenue arrivals from Betulia and Kaysen are all pointing at the same thing. This is a market that is willing to underwrite serious cooking.
If you live here, the practical move is to stop treating summer as the off-season and start treating it as the R&D window. The reservations you cannot get in February are the walk-ins you can get in July, and the operators are motivated to make you a regular before the season buyers arrive.
When the season does turn and conversations shift toward second-home plans, marina life, or a waterfront move, The Sprigg Group knows the coast the way you know your dining map. Create Your Paradise — Start Your Waterfront Search.
