On the mend from hurricanes, Anna Maria Island still feels like Old Florida

The most photographed spot on Florida’s Anna Maria Island, if not second to photos of the sun setting over the Gulf of Mexico, may be the Old City Jail.

The rough stone structure is graffitied with the words, “No roof, no doors, no windows, no bars, no guests for yrs n’ yrs,” and makes for a quirky photo opportunity. A plaque tells me that in 1927, revelers from a nearby dance hall were jailed for public disturbance. The jail, which had only bars on the windows, left the prisoners exposed to Florida’s ferocious mosquitoes all night long. Needless to say, the dancers were on their best behavior after that.

But what captured my interest most during my visit to this sleepy Gulf Coast barrier island wasn’t the famous old jail — it was its next-door neighbor, Belle Haven Cottage.

Built in 1920, the cottage has worn many hats over the years — a fish packing plant, a rental retreat and a bait shop. Today, it serves as a temporary home for the Anna Maria Island Historical Society’s antiques and heirlooms while the society’s museum undergoes repairs from the damage left by Hurricanes Helene and Milton last fall.

Belle Haven has withstood more than a century of storms like those, both serving as a piece of the island’s history and now protecting it.

That resilience was evident everywhere I looked on Anna Maria Island. Mere months ago, there was 3 feet of standing water in several businesses, and sand was piled along roads and against buildings.

But repairs had been made and daily life in Anna Maria seemed to have returned to normal when I visited in January, though subtle reminders of recovery remained. Construction crews were busy at work, rebuilding what the hurricanes had taken.

One morning, I picked up a pastry and coffee from Mademoiselle Paris French Restaurant & Bakery and walked four blocks to the other side of the island, planning to enjoy breakfast at the landmark Anna Maria City Pier. But when I arrived, I found the pier still closed, its wooden planks swept into the Anna Maria Sound months before.

Arriving on the island after a 30-minute drive from Sarasota Bradenton International Airport, I’d checked into Bungalow Beach Resort, in a classic 1930s-style low-slung cottage that I almost missed among the pastel-colored hotels and motels lining the beaches. Owned by lifelong Floridians, the Sand Dune Bungalow is a beautifully preserved piece of coastal history, adorned with vintage postcards and photographs that capture the spirit of Old Florida.

Once part of a trio of bungalows at the resort, this charming cottage is now the last one standing after the devastating 2024 hurricanes. (The resort recently restored its rental options by adding a duplex next door.) The bungalow carries nearly a century of memories while providing a peaceful retreat by the sea. With direct access to the beach, my days unfolded in a rhythm of simple pleasures — strolling along the water’s edge in search of delicate shells, sinking into a lounge chair with a beach read, and sipping fresh coconut water from nearby Surfing Coconut as the waves rolled in.

One of the most special parts of the Anna Maria Island experience is the relative lack of chain businesses. The only chains are a grocery store, a pharmacy and maybe a few other essentials. Instead, everything feels new to visitors, who can spend their days relaxing at the beach or biking and walking between mom-and-pop gift stores full of seashell-encrusted picture frames, sunset paintings and other ocean-themed knickknacks. Nights are spent dining at quaint beachside restaurants and bars, where the house specialty is often fresh-caught grouper from the Gulf of Mexico (or Gulf of America, if you prefer).

With swaying palms and colorful stores, Pine Avenue feels like its own little slice of Old Florida. This walkable street is lined with charming boutiques, art galleries and breezy cafes, all steps from sugar-white beaches. You can browse coastal clothing from local brands at Pink & Navy, find artisanal cooking and dipping oils at the Olive Oil Outpost, or indulge in a slice of homemade Key lime pie from Hometown Desserts.

I stopped into Shiny Fish Emporium to pick out a birthday gift for my sister. The small store, owned by a husband-and-wife duo, is full of bright clothing and baubles, mostly in delicate shades of pink. While it was quiet on the sleepy morning I visited, I could imagine the store full of doting grandparents and their grandchildren, painting sand dollars and picking out souvenirs together.

As I wandered the aisles, Dan, one of the owners, shared stories of how this little retail district prepared for the hurricanes. I learned that Flex Seal is better at keeping floodwater out than sandbags, and how his family and neighbors came together to fix up their stores again. With no support from corporate parent companies, business owners and the community picked up the pieces to welcome visitors back.

On my last night on Anna Maria Island, I met up with a childhood friend who had recently moved to nearby St. Petersburg for dinner at the Porch, an upscale restaurant housed in a historic building. Over steaks, seafood and glasses of wine, we reminisced and caught up on the last few years before saying our goodbyes.

Despite the uncharacteristically cool night, I couldn’t resist one last walk along the beach. The shoreline was empty, bathed in soft moonlight, the waves whispering against the sand. Here, far from the glow of Tampa Bay, the sky stretched wide and unspoiled, save for the sparkling constellations that loomed over the gulf. As I stood at the water’s edge, toes sinking into the cool sand, I felt the quiet, timeless magic of the island.

While pieces of its past have been swept away into the ocean, Anna Maria Island still feels like an escape to Old Florida, with kitschy charm and postcard-perfect beaches — just like in the vintage photos that adorned the walls of my bungalow.