Drive down Estero Boulevard past Times Square on any given week this summer and you'll pass two kinds of businesses standing a few hundred feet apart. One has rebar in the ground and a foundation being poured. The other has a generator humming behind a serving window, tables set up on gravel, and a laminated menu clipped to a stand. Both are open. Both are serving customers. Only one of them is betting on staying.
That distinction, permanent construction versus a truck or trailer that can be hitched up and moved, is the single clearest signal for anyone trying to read how the island is actually doing right now. Not the beach itself, which has been fully renourished and looks as good as it did before the storm. Not the tourism numbers, which bounce around with the season. The tell is in what property owners are willing to build versus what they're still hedging on nearly four years after Hurricane Ian.
The Two Kinds of Businesses on This Island Right Now
If you've lived here through the rebuild, you already sort places into these categories without thinking about it. It's worth naming them out loud, because the mix is shifting month to month.
Back for good, in permanent locations:
- South Beach Grille, reopening in Santini Plaza, had targeted a grand opening around mid-July, one of the most anticipated returns on the south end. It was a go-to hangout for residents before the storm, and its comeback in a rebuilt storefront rather than a trailer says something about the owners' confidence in that stretch of the island.
- Jersey Mike's, also landing in the Key Estero Shopping Plaza, was working toward a similar mid-July opening window, a national chain betting on the island's rebuilt retail corridor.
- Lah De Dah Beach Bar & Grill, inside Margaritaville Beach Resort, has been a reliable lunch and dinner option since the resort itself came back newer and more storm-hardened than most of what surrounds it.
Still testing the water:
- Sol Tequila, taking over the old Mr. Tequila spot in Key Estero Plaza, is aiming for a September 2026 opening. It's the same family and mostly a name change, but it's still in the build-out phase rather than serving.
- Mom's Restaurant, a longtime comfort-food institution on Estero Boulevard, was still running as a food truck at its original location as of this spring, years after the storm. The menu, the Buttermilk Biscuit Sandwich, the Chicken Salad Biscuit, the Meatloaf Grilled Cheese, the cinnamon rolls people used to drive across the bridge for, hasn't gone anywhere. The building it used to occupy has.
None of this means the truck operators lack confidence in the island. Running a truck can be a practical first step while permits and financing catch up, and food trucks have genuinely kept parts of Fort Myers Beach fed and social since 2022. But there's a real difference between a business that's building for the next twenty years and one that's still deciding.
Why an Ice Cream Shop Broke a Four-Year Stalemate
For most of the time since Ian, Times Square existed in the kind of limbo where everyone had an opinion about what should happen there and nothing actually got built. That changed in December 2025, when the Town Council unanimously approved a three-story mixed-use building on the former Kilwins site at 50 Old San Carlos Boulevard, about a hundred feet from where the old pier used to stand.
The project is modest by square footage. Ground floor houses an ice cream vending concept called Meli's Ice Cream Shop, owned by Carlos Chavez, with a one-bedroom residence for his family spanning the second and third floors. The town granted a floor area ratio deviation from 1.8 to 2.5 to make it work on a lot just under 1,200 square feet, squeezing in nearly 2,800 square feet of development. Chavez also agreed to pay toward a future wave-mitigation wall if the town builds one.
The scale isn't the point. The approval is. It's the first permanent building anyone has actually gotten through the process in the district that used to be the commercial heart of the island, and it broke a standoff that had left Times Square running on ice cream trailers and pop-up counters since the storm.
It's not the only sign that permanent capital is starting to move. A short walk away, a developer that originally proposed a 31-room hotel near Times Square saw that plan rejected by the Town Council last year after local pushback. The revised, smaller project was slated to start construction in early July 2026, a $13 million investment that shows the same pattern: ambition gets scaled down to fit what the island and its residents will actually accept, but the building still gets built.
The Pier Is Still Waiting on Washington
Not everything is moving at the same pace. The Fort Myers Beach Pier, the 560-foot landmark that anchored Lynn Hall Memorial Park and gave generations of residents a place to fish and watch the sunset, is still stuck in federal review nearly four years after the storm destroyed it. As of March 2026, the U.S. Army Corps of Engineers was still reviewing Lee County's rebuild plans, a fact that frustrates the people who own property nearby.
Shlomo Melloul, a developer who's proposed a three-story building with a rooftop bar on two Times Square parcels facing where the pier used to stand, put it plainly back in March 2026 when asked about the delay:
"This is a long time."
His own project, unlike Meli's Ice Cream Shop, hasn't cleared the approval process yet. It's still plans on paper, submitted but not voted on, which puts it in the same waiting category as the pier itself. Current guidance points to a pier completion sometime around August 2027, which would put the rebuild timeline at just under five years from the day Ian made landfall. That's the kind of number that only means something once you set it against Meli's four-month path from Kilwins demolition site to unanimous council approval. Some projects on this island move at the speed of a local vote. Others move at the speed of a federal agency, and residents are living through the gap between those two clocks.
What Never Actually Left
While all of that construction math plays out, the parts of daily life that don't require a building permit never really stopped. The Santini Farmers Market runs every Tuesday and Thursday morning through the winter and spring season, most recently from November 2025 through the end of April, and it will return again this fall. It sets up near a cluster of businesses that made it through the storm intact: The Book Nook, Leani's, Bad Ass Coffee, Surfstyle, Sweet Licks Ice Cream, and Ace Hardware. It's an easy walk from several condo buildings and timeshares on that stretch of Estero Boulevard, and it's been described more than once as a place voted a neighborhood favorite going back to when it was established in 2010.
The Fort Myers Beach Market, on Old San Carlos across from SOB's, holds the distinction of being the first market on the island to reopen after Ian, a detail longtime residents tend to remember even if visitors don't. Beach Baptist Farmers Market runs Wednesdays and Fridays from October through May, free parking, dog friendly, proceeds supporting a coffee mission in Guatemala.
None of these markets needed a Town Council vote or an Army Corps review to keep running. They're a reminder that the island's actual social fabric, the produce vendors, the coffee stand regulars, the Tuesday morning routine, was never as dependent on Times Square's rebuild as the headlines suggested.
The Calendar Fills In Around the Construction
The rest of the year's rhythm has filled back in too. Cars & Coffee at Santini Marina Plaza brings out classic and specialty car clubs on select summer mornings, coffee and breakfast on site, free and open to the public. Bayside Veterans Park has been running a concert series this summer, with acts like The Bed Banditos and Guilty Pleasure taking evening slots earlier this month. The Mound House hosted a Summer Lecture Series this season, including an August 13 talk on weather forecasting and the region's changing climate, a fitting subject for an island that spends a lot of its year watching the tropics.
Wings on the Beach, an island-wide competition featuring a dozen local restaurants each serving up their own take on a chicken wing, crowns a Golden Wing Champion every year and gives residents a reason to walk the length of the island in an afternoon. The Island Hopper Songwriter Fest brings touring songwriters into local bars and beachfront venues for a weekend that's become one of the more anticipated stops on the island's calendar.
Reading the Concrete
If you want an honest read on how Fort Myers Beach is doing, skip the summary language about resilience and recovery and just count. Count how many storefronts have poured foundations versus how many are still running out of a truck. Count how long a project sat in front of the Town Council versus how long it's been waiting on a federal agency. Count the markets and events that never needed anyone's approval to keep going, because those numbers tell you where the island's confidence actually sits right now, not where a press release says it should be.
The island isn't finished rebuilding, and pretending otherwise doesn't help anyone who lives here. But the gap between Meli's Ice Cream Shop breaking a four-year stalemate and the pier still waiting on Washington is the most honest map of the place you'll find.
If you're weighing a move within the island, thinking about a waterfront purchase here, or just want a second opinion on what a property's rebuild status actually means for its value, iConnect RE has spent years watching this exact recovery play out parcel by parcel. Schedule a consultation when you're ready to talk through what you're seeing on the ground.
