10 Florida Islands Locals Say Don’t Feel Like Old Florida Anymore
Florida’s islands once stood as shorthand for escape, places where time bent toward tides, cottages leaned into sea breezes, and life moved with a hush. Over the years, growth, storms, and demand have reshaped many of them.
What were once sleepy hideaways now carry shinier storefronts, fuller resorts, and crowds that never quite leave. And yet, if you know where to look, the spirit lingers. It hides on back lanes shaded by palms, in quiet coves where the water still feels timeless, and in the stories of family-run spots that haven’t changed.
Each island has its own balance of memory and reinvention. Here are ten Florida islands where traces of “Old Florida” are still waiting to be found.
1. Key West
Roosters strut the side streets while Conch houses sag gracefully under their pastel paint. The lanes away from Duval still feel like a painter’s sketchbook.
Step onto the main drag, though, and it changes. Cruise-day crowds fill bars, and shop windows flash neon instead of lantern light. The island hums louder now.
I wandered back toward the harbor and found quiet again. Sitting under a leaning palm, I realized Key West rewards detours more than itineraries.
2. Marco Island
The skyline rising over the sand tells its own story: towers, balconies, and a carefully pruned waterfront. It looks more like a brochure than a memory.
Marco began as a low-rise refuge, known for shelling walks and beaches that stretched without interruption. Those roots peek through in history boards scattered around.
Try sunrise walks. Before beach chairs fill the horizon, pelicans glide just as they always have, and the island feels closer to its simpler beginnings.
3. Sanibel
Shells crunch underfoot in the same familiar way, though the backdrop has shifted. The horizon holds construction cranes alongside shorebirds.
Hurricane Ian’s aftermath brought rebuilding, and with it came new footprints, sleeker houses, pricier rentals, and a different pace. The relaxed rhythm is tougher to find.
Early morning still carries the Sanibel I imagined. Bending down to collect shells with the tide sliding in, I felt part of the long line of visitors who once knew the island as purely quiet.
4. Captiva
Shells crunch underfoot in the same familiar way, though the backdrop has shifted. The horizon holds construction cranes alongside shorebirds.
Hurricane Ian’s aftermath brought rebuilding, and with it came new footprints, sleeker houses, pricier rentals, and a different pace. The relaxed rhythm is tougher to find.
Early morning still carries the Sanibel I imagined. Bending down to collect shells with the tide sliding in, I felt part of the long line of visitors who once knew the island as purely quiet.
5. Anna Maria Island
Local chatter points out how sunsets here have become an event in themselves. Crowds line up phones ready, chasing the orange glow.
The island once moved slower, full of small beach cottages and short-term stays that never felt overwhelming. Now rentals stack up, and peak weeks squeeze the lanes.
Aim for weekdays outside holidays. The island still has pockets of its gentle self, especially early mornings, when the sand is dotted only with shells and herons.
6. Siesta Key
The sand still powdery-white, cool even under noon sun, is the first thing you notice. It’s dazzling in a way that hasn’t changed.
Around it, though, the atmosphere has shifted. Louder seasons bring busier lots, night crowds stretch later, and the energy is less about calm than about celebration.
Walking the shoreline at dawn, I understood why people cling to this beach anyway. Before the music starts, it’s just water and sand, as soft and timeless as ever.
7. Clearwater Beach (Barrier Island)
North and south of the pier, the sand feels calmer, with smaller motels holding on and fewer umbrellas dotting the horizon. The edges breathe easier.
Step closer to the center, though, and towers dominate the skyline. Events fill the calendar, and the boardwalk buzzes with a pace that never seems to pause.
Tip: wander beyond the pier if you want a glimpse of the earlier Clearwater. The beaches away from the hub still carry that slower charm.
8. St. Pete Beach
Retro motels in bright pastels still hold ground, their neon buzzing softly as night sets in. They hint at the strand’s long memory.
But larger hotel brands now share the same sand. The beach road fills with traffic, though always slower than the glossy brochures suggest. Growth is steady but not subtle.
Early evenings felt best here. Watching locals walk dogs past old signage reminded me that the island still wears its retro skin proudly, even as the landscape shifts.
9. Key Largo
The highway stretch through town hums with busy traffic, lined with dive shops, chains, and restaurants vying for drivers’ attention. It feels like an entry point more than a hideaway.
Beneath that noise, the water still tells a softer story. Early paddles through creeks reveal mangroves and herons, the quiet that once defined the island.
I carried that contrast with me. Between highway bustle and kayak stillness, Key Largo felt like two places layered together, both real, both holding their ground.
10. Amelia Island
Downtown Fernandina still greets visitors with Victorian storefronts, shaded sidewalks, and the kind of architecture that feels preserved in amber. The charm hasn’t faded.
Yet, much of the main visitor experience has shifted. Resorts and golf carts steer the rhythm now, with manicured lanes that smooth over the island’s older quirks. It’s a different kind of polish.
Walking side streets helped me find the balance. Between weathered porches and shaded parks, Amelia still shows its gentler side, even if it takes a little searching.