"Our fishing town is now becoming an art town." Stephanie Cox didn't hedge when she said it at a recent public meeting. She runs the nonprofit that spent fifteen years making it true: the Morada Way Arts & Cultural District, six blocks that most of us treated for years as a stretch of highway you passed on the way to somewhere else. This year those six blocks became somewhere else themselves, the first place in Islamorada where you can park once, eat dinner, wander into a gallery, catch live music, and drive home without ever moving your car.
Nobody built this on purpose, at least not as one project. What actually happened is that two unrelated efforts, a slow-building arts district and a private fishing club forced to rebuild from scratch, both hit their stride at the same time, on the same half-mile of Old Highway. Neither one planned it that way. Together they changed what a Tuesday evening in the village can look like.
From One Gallery to a Full Block
Morada Way runs between two landmarks every local can picture without checking a map: the Hurricane Monument to the north and the Green Turtle Inn to the south, roughly Mile Marker 81 to 82. The nonprofit that organizes the district describes it as the only walking arts corridor in Islamorada, and the largest one anywhere in the Keys outside Key West.
That description would have sounded generous five years ago. The district's events chair remembers a time when Jessica Ann Art was the only studio with its lights on. The growth since then has come in bursts rather than a straight line, most of it in the last three years, and it shows in what's actually open on a given night now:
- Gallery Morada, the anchor space at the corner of Morada Way and Old Highway
- Wonder & Wyld and Morada Way Clay, both now part of the regular gallery stops
- Florida Keys Brewing Company, part taproom and part gallery space, with an outdoor beer garden
- Seven restaurants within an easy walk of each other: Kaiyo Grill, Chef Michael's, Ma's Fish Camp, Green Turtle Inn, Islamorada Fish Company, Morada Bay Café, and Pierre's
The Third Thursday Art Walk has run on this stretch since 2011, six to nine in the evening, and for most of that run it was a nice event inside a mostly empty corridor. What changed isn't the event. It's that the storefronts around it finally filled in enough that the corridor works as a place to spend an entire evening, not just ninety minutes once a month.
A Private Club Filled In the Other Half
A few minutes up Old Highway, on Madeira Road, a much older institution went through its own forced reinvention. The Islamorada Fishing Club started in 1950 at what was then Dewey's Bait and Tackle Shop, and the membership bought the property outright in 1955. The original clubhouse stood on that same lot for nearly seventy years until it was demolished in 2023 to make way for something bigger.
The new three-story building opened on Thanksgiving, and 2026 marks its first full calendar year in operation. It's a private club, so it isn't a spot anyone can walk into off the street the way you can with a gallery on Morada Way. But its return changes the texture of that end of the village anyway. The rebuilt clubhouse has a rooftop lounge with seating for 80 and unobstructed bay views, a second-floor dining room with an elegant bar, and a menu built around wood-fired pizza, charcuterie, and raw bar plates. General manager Vinnie Feola and chef Oscar Pajares have leaned into the seafood-forward side of the menu. As Pajares put it, "Octopus is the thing to have from the bar menu."
The tarpon, sailfish, and member-guest tournaments that built the club's reputation are back at the storied Madeira Road address too. This year's calendar included the Captain's Cup Sailing Tournament in January, the Golden Fly Tarpon in mid-May, and a run of fly-fishing tournaments, the Don Hawley Invitational, the Ladies Tarpon Fly, and the Gold Cup Tarpon, that filled most of June before the Captain's Cup Dolphin Tournament closed out the month. Weekly prime rib nights and rotating Sunday brunches are back on the calendar too. The club's conservation arm also opened its doors for at least one public-facing event this year, an informational session on the effort to Save Alligator Lighthouse that drew more than 60 attendees.
None of that makes the fishing club a public amenity. What it does is put a second, unmistakably local landmark back on the map at the exact moment Morada Way was filling in six blocks away. A village this size doesn't get many chances to have two anchors reactivate in the same year.
The Restaurants That Filled the Gaps Between
Dining picked up outside the walking district too, which matters because it means the six blocks aren't carrying this alone. Papa Joe's Waterfront reopened in 2024 on the exact footprint where the original restaurant operated for almost 75 years before it was demolished in 2010. The site sat empty for over a decade, so its return closed a gap that had been part of the village's skyline for most of a generation.
On Plantation Key, Tony and Isis Wright, who already run Italian Food Company locations in Islamorada, Tavernier, and Key Largo, opened a fourth concept called Lido 73 at 90451 Old Highway, an indoor-outdoor spot built around a waterfront setting with breakfast service daily. It's a different stretch of the village than Morada Way, but it's more evidence that the dining scene isn't just clustering in one six-block pocket. It's thickening across the whole village at once.
One Practical Thing Worth Knowing This Month
If your evening errands or your drive home take you through Plantation Key, pad in a few extra minutes for the rest of the summer. The Florida Keys Aqueduct Authority finished connecting a new 36-inch steel water main running more than six miles from Snake Creek Bridge to Julep Road, with the line fully flowing since mid-July. The part still in progress is the flushing of that transmission main, expected to continue through the end of August, followed by paving work scheduled to run from August into September. It won't affect Morada Way or Madeira Road directly, but it's the kind of evening traffic detail that's easy to miss until you're stuck in it.
What Actually Sticks Around
The pipeline work will finish. The paving will get done before the weather turns. What's more durable is the six blocks that already exist, already busy on the third Thursday of every month, and already the closest thing this stretch of the Keys has ever had to a downtown you can walk end to end. Add a fishing club running a full slate of tournaments again for the first time in years, and this has been a genuinely unusual twelve months for a village that has spent most of its history built around driving from one destination to the next rather than parking and staying.
None of this happened because anyone planned a district. It happened because a nonprofit kept adding one studio at a time for fifteen years, and because one clubhouse had no choice but to rebuild from the ground up. The two timelines happened to cross this year. Next year they might not line up so neatly again, which is part of why it's worth noticing while it's still new.
Ally Kelley has spent years watching Islamorada's small shifts add up to something bigger, the kind of local detail that shapes daily life long before it shows up in a listing description. If you're curious how changes like these are shaping the Middle and Upper Keys, or you'd simply like a local perspective on the market, Ally Kelley is always glad to talk.
