One year ago, back-to-back hurricanes battered Florida’s Gulf Coast — first Hurricane Helene, then Hurricane Milton just a few weeks later.
And one of the hardest-hit places was Anna Maria Island, a seven-mile stretch of paradise that sits just below Tampa Bay.
Helene made landfall near Perry, far up in the Big Bend region, but its massive size pushed storm surge three to five feet high all the way down the coast. Then, on October 9th, Hurricane Milton slammed into Siesta Key as a Category 3 storm — just a short distance south of Anna Maria.
Helene flooded the island. Milton finished the job.
So, one year later, I went back to see what’s changed, what’s still gone, and what’s come back even stronger.
A Small Island with a Big Personality
Anna Maria Island — or AMI, as the locals call it — is squeezed between St. Petersburg to the north and Sarasota to the south.
It’s only seven miles long, but it’s one of the most charming beach towns in Florida: pastel cottages, walkable streets, and not a high-rise hotel in sight.
This isn’t a place for theme parks or nightlife. It’s a place where you ride bikes to the beach, grab a Cuban sandwich at a mom-and-pop shop, and watch the sunset instead of your phone.
And that’s exactly why it was so painful to see it under water last year.
The Rod & Reel Pier — Gone but Not Forgotten
If there was a single image that captured the soul of Anna Maria Island, it was the Rod & Reel Pier.
This Old Florida-style fishing pier and seafood restaurant was so iconic that it even appeared on the cover of “Visiting Small Town Florida” by Bruce Hunt.
Today, it’s gone. Hurricane Milton took it completely — nothing left but splintered pilings and memories.
There’s a sign promising to rebuild, and a new land-based version of the restaurant is in the works. But for now, the spot where the pier once stood has become an informal memorial. Locals and visitors leave behind shells, trinkets, and hand-written notes to what was once the heart of the island.
Anna Maria City Pier — Rebuilding Slowly
The City Pier, another landmark, was also damaged. Parts of its walkway were ripped away, leaving only the restaurant at the end intact.
City officials say the rebuild is underway, but recovery takes time on a small island. What’s still standing is a reminder of both destruction and resilience — the kind of place where people still come to fish, even when there’s not much pier left to stand on.
Pine Avenue: America’s Greenest Main Street
A few blocks inland, life feels surprisingly normal again.
Pine Avenue, often called “America’s Greenest Main Street,” is full of eco-friendly local shops and small businesses.
No chain stores. No neon signs. Just pastel bungalows with solar panels and hand-painted signs.
I stopped by the Anna Maria General Store for a Cuban sandwich — and I’m not exaggerating when I say it deserves its own recovery award.
There are still a few scars here and there — weathered paint, cracked stucco — but the energy is back. The people here clearly take pride in keeping AMI’s “old Florida” vibe alive.
The Historical Museum and the Old Jail
At the Anna Maria Island Historical Museum, I saw where the floodwater reached nearly three feet high during Helene.
Volunteers pointed out the waterline inside — a literal reminder of how deep things got.
Out back, you’ll find one of Florida’s strangest landmarks: the Old City Jail. Built in the 1920s, it had no roof, no bars, and no air-conditioning. Locals used to say you’d spend a night there “cooling off” — if the mosquitoes didn’t convince you to behave first.
Bean Point and Passage Key
At the very northern tip of the island is Bean Point Beach, a wide, quiet stretch of paradise.
It’s breathtaking — turquoise water, powdery sand, and sometimes even manatees gliding past the shore.
The lack of parking keeps it peaceful; it’s mostly locals and those willing to bike or walk in.
From Bean Point, you can see Passage Key, a small island just offshore. It’s a federally protected bird sanctuary — and, depending on who you ask, also a clothing-optional hangout known locally as “Naked Island.”
Only in Florida.
The Sandbar and Captain Anthony’s Seafood
Down at Anna Maria Island Beach, things look lively again. The Sandbar Restaurant is open, packed, and serving sunset dinners right on the sand.
But just down the road, I met the owners of Captain Anthony’s Seafood, who told me a much tougher story.
They suffered nearly $300,000 in damages when Helene hit. Their business and home were almost completely wiped out.
They showed me photos of their flooded shop — and of the world-record fish they’ve caught over the years.
They told me how locals helped them find pieces of their equipment scattered across the island — even a freezer that floated three blocks away.
If there’s a silver lining to hurricanes, it’s the way communities like this pull together. Listening to them, you realize: resilience here isn’t just about rebuilding buildings. It’s about rebuilding lives.
Holmes Beach: Small Town Laws with Big Impact
Holmes Beach looks great today, but it also tells an important story about what makes Anna Maria Island unique.
Years ago, residents passed an ordinance banning high-rise construction to preserve the island’s small-town feel. The only exceptions — the Martinique Condos — are still standing (and still considered eyesores by many locals).
There’s also a local rule limiting chain restaurants. Besides a Dunkin’, a Domino’s, a Publix, and a CVS, everything else here is locally owned. That’s part of what gives AMI its sense of place.
This isn’t a resort island. There are no big hotels, no Margaritaville.
Most visitors stay in small boutique inns, beach cottages, or Airbnbs.
You don’t come here for theme parks — you come to slow down, ride a golf cart, and live like a local for a few days.
Manatee and Coquina Beaches
The island’s two biggest public beaches — Manatee Public Beach and Coquina Beach — are both looking great.
Manatee Beach is the island’s main hangout, with a big café, volleyball courts, showers, and the largest lifeguard tower I’ve ever seen.
Parking fills up fast, though, so get there early or take the free trolley that runs the length of the island.
A few miles south, Coquina Beach offers a more laid-back vibe, shaded by tall pines and surrounded by walking trails and picnic spots.
If Manatee is the social hub, Coquina is the exhale — quiet, breezy, and beautiful.
And no, Manatee Beach isn’t named for actual manatees. It’s Manatee County.
Bridge Street and The Drift In
At the southern tip of the island, Bridge Street is where the action is — bars, shops, live music, and even a mini-golf course right in the middle of it all.
The Bridge Street Pier was damaged in the storms but has since been repaired. You can fish here again, or grab dinner at the Anna Maria Oyster Bar at the end of the pier.
And then there’s The Drift In, the island’s most legendary dive bar.
It turns 100 this year — and it comes with an incredible story.
As the legend goes, Babe Ruth was a regular here back in the day. After a long night of drinks, he accidentally left without paying his tab. The next morning, he came back to make it right — and ended up buying the entire bar instead. He ran it for a few years as a tribute to his father, who’d owned a bar back home.
For decades, The Drift In was a locals-only dive that smelled like beer, bait, and bad decisions. Today, it’s still a dive bar — just a more approachable one. The Babe’s memorabilia still covers the walls, and the regulars still tell stories that sound just barely believable.
One Year Later
Driving around the island today, you’ll still see work trucks, roofers, and construction crews. Some homes are gutted. Some signs are still broken. But the island is open. The beaches are clean. The sunsets are just as beautiful as ever.
So, what happened to Anna Maria Island?
It got hit. Twice.
And it came back.
This is Florida’s most resilient little island — still charming, still local, and still one of the most beautiful places in the Sunshine State.
Planning Your Visit
Best way to get around: Free trolley, bike, or golf cart.
Parking tip: Arrive early or park off-island and trolley in.
Can’t miss stops: Pine Avenue, Bean Point, The Drift In, and the Sandbar Restaurant.
Closest airport: Sarasota-Bradenton (SRQ), about 40 minutes away.
