Drive the length of Estero Boulevard on a Friday night this summer and you'll pass three different versions of recovery. Near the bridge, where Times Square used to hum with tourists, there's mostly open space and exactly one project that has actually cleared every approval it needs. A couple miles south, past the spot where the old Town Hall stood, a food truck park just broke ground next to a condo building whose residents are suing to stop it. Keep driving to the south end and you'll find a plaza that looks close to whole again, with three sit-down restaurants pouring drinks on a Friday night like nothing ever happened.
If you live here, you already know the island doesn't feel evenly back. What's less obvious is why. It's not that some areas are trying harder than others. It's that the island is running three different kinds of rebuild at once, on three different timelines, and none of them are waiting for the others to catch up.
The South End Got Its Restaurant Back First
Santini Plaza, at 7205 Estero Boulevard, took the hardest early hit. Hurricane Ian wiped out Oliver's Place, Skye's, Sand Bar, and the Subway in one pass, and for months afterward, south-end residents drove to Bonita Springs or up to the island's north end just to sit down for dinner.
That gap started closing this year. South Beach Grille moved into the old Oliver's Place space, a 4,782-square-foot buildout that plaza owner Yariv Shaked originally hoped would open by New Year's Day. It didn't. The grand opening slipped to mid-July, which tells you something honest about how recovery actually moves here: even the most straightforward project, dropping a familiar restaurant back into an existing shell, ran more than six months past its own target.
It's open now, and it's not alone. Skye's is back serving Fresh Mex on the same pet-friendly patio it had before the storm. Sandbar and Grille has reclaimed its spot as the south end's sports bar. Legno Italian Kitchen opened its doors too, and owner John Maffei described the response from neighbors in blunt terms:
"We opened the doors and the whole community supported us right away. The community is amazing here."
Longtime residents Joe Mceneaney and Paul Budil put it differently, calling the plaza their "little downtown on the south end." Sweet Licks Ice Cream, Leanis Swim and Casualwear, and The Islander have filled back in around them. For anyone living south of mid-island, the drive to dinner got a lot shorter this year.
The Middle of the Island Is Still Running on Food Trucks
Head north from Santini and the picture changes fast. Near where the old Town of Fort Myers Beach Town Hall used to sit, at 2500-2510 Estero Boulevard, a very different kind of project just broke ground: Access 26, a food truck park and beer garden named for the public beach access point next door.
Owners Jamie Hotka and Dan Myers spent more than a year getting this approved, and the fight over it says something about what rebuilding actually costs socially, not just financially. The site sits next to the Pelican Watch condo building, close enough that the community pool is just a few feet from the property line. Neighbors David and Helen Tezak sued the town over the approval, arguing it amounted to spot zoning that violated the town's comprehensive plan. That lawsuit is still active even as Stevens Construction breaks ground on the two-story, 3,000-square-foot structure, which will eventually include Manny's Scoops ice cream shop, a retail area, and a bar with covered seating.
Mayor Dan Allers showed up for the groundbreaking in June, which tells you the town sees this as a milestone worth celebrating, not just tolerating. But it's worth sitting with what Access 26 actually is: not a restaurant reopening, but new food infrastructure built around trucks and outdoor seating because that's what's fast to permit and cheap to insure right now. A few blocks south, Mom's Restaurant is still running out of a food truck at its original Estero Boulevard location while its owners work out how to rebuild the real thing. That's the middle of the island in 2026: real food, real crowds, but built around structures that were never meant to be permanent.
Times Square Has One Approved Building. That's It.
Then there's the part of the island most visitors still picture when they think of Fort Myers Beach: Times Square, the plaza across from Lynn Hall Memorial Park where the pier used to draw the evening crowd.
Nearly three years after Ian erased it, Times Square got its first approved permanent building this past December. It's not a restaurant complex or a hotel. It's a three-story building with a ground-floor ice cream shop, Meli's, replacing the old Kilwins on a lot at 50 Old San Carlos Boulevard, with a one-bedroom apartment above it for the property owner, Carlos Chavez, and his family. The lot is barely 1,195 square feet, and the town had to grant a floor-area ratio deviation just to make the project pencil out under current flood elevation rules.
It is, by any measure, a small building. But its significance isn't in its size. It's the first concrete example, literally, of what a compliant rebuild in that district can look like after years of debate over whether Times Square should come back bigger or come back smaller. A second, larger proposal from developer Shlomo Melloul, a three-story building with a rooftop bar and retail space at the corner facing the pier site, was still working through the approval process as of this spring, the most recent update available. Nothing on that corner has broken ground yet.
So if you're waiting for Times Square to feel like Times Square again, with the density of bars and shops that once anchored the island's tourist season, you're waiting on a process that took nearly three years to produce its first ice cream shop.
Three Miles, Three Timelines
None of this means the island isn't recovering. It means the recovery doesn't move as one thing, and treating it that way is how you end up disappointed by news that should actually be good.
If you live near the south end, your daily options this year genuinely multiplied. If you're closer to the middle of the island, what's arriving is food truck infrastructure that residents are still arguing over in court, not a restaurant row. And if your mental image of a night out still centers on Times Square, that image is going to keep not matching reality for a while longer.
Here's a quick read on what's actually open and where, as of this year:
- South end (Santini Plaza, 7205 Estero Blvd): South Beach Grille, Skye's, Sandbar and Grille, Legno Italian Kitchen, Sweet Licks Ice Cream
- Mid-island (near 2500 Estero Blvd): Mom's Restaurant, operating as a food truck at its original location; Access 26 food truck park and beer garden, under construction
- Key Estero Plaza: Sol Tequilla, targeting a September 2026 opening; Jersey Mike's, which had set a tentative July 15 opening date
- Times Square: Meli's Ice Cream Shop, approved and the first permanent post-Ian building in the district; a second, larger rooftop-bar proposal still under review
- Margaritaville Beach Resort: Lah De Dah Beach Bar & Grill, open and serving
None of these categories will look the same a year from now. That's the nature of an island rebuilding under stricter flood codes and tighter insurance math than it had in 2022. But knowing which stretch of Estero Boulevard is actually moving, and which is still working through permits, lawsuits, or both, is the difference between being surprised by the island and understanding it.
I've spent enough years on the construction and permitting side of Southwest Florida to know that a groundbreaking and a grand opening are two very different milestones, and that the gap between them is where most of the frustration lives. If you're trying to make sense of what's changing on this island, whether you're deciding where to eat tonight or thinking further ahead about property here, I'm happy to talk through what I'm seeing on the ground. You can reach out anytime through Jonathan Gunger.
