Visitors are drawn to Anna Maria Island by the warm, inviting waters of the Gulf of Mexico and the pristine stretches of white sand beaches. But the same qualities that make the Island so enticing also leave it particularly vulnerable to storm surges and flooding. The sandy soil quickly becomes saturated, leaving excess water to pool in low-lying areas. Meanwhile, the Island’s flat topography limits the natural flow of water and exacerbates flood risks. Even a thunderstorm can cause temporary but significant flooding on Anna Maria Island. The one-two punch of Hurricanes Helene and Milton brought devastation that was unlike anything its residents had ever experienced.

“You’re not meeting anyone that hasn’t been affected by this to some extent,” says Darcie Duncan. “Every single property, every single business except maybe a small handful. Everybody’s in the same boat.” Duncan, an Island native, is the owner of Duncan Real Estate. In addition to selling properties, her firm offers property management services and manages many of the vacation rentals that have proliferated in recent years. While Duncan was able to reopen her Holmes Beach office fairly quickly, her office on Pine Avenue in Anna Maria took on substantially more damage and required a lengthier closure. Duncan’s focus isn’t on herself, though: since day one, she has spearheaded community-driven relief efforts. In the immediate aftermath of Helene, when roads to the Island were closed, Duncan had supplies including food and water delivered by boat to her dock and distributed them to people who needed them. She started a Facebook group called Anna Maria Island Hurricane Relief to open up lines of communication which currently boasts over 8,000 members. In November she realized that many islanders still wouldn’t have access to working kitchens so she decided to organize a community Thanksgiving meal at The Center of Anna Maria Island, an event that was attended by over 400 people with much of the food provided by local restaurants and expenses covered by private donations. “If I have to say one thing about myself, I’m a good connector of people,” Duncan says. The Center of Anna Maria Island (or The Center as it is more colloquially known) is a nonprofit community center that has served the Island’s population for decades. After Helene, it became a sort of de facto emergency operations center. “We were able to use The Center as a hub of community resources. We immediately started a volunteer database for people who needed help at their houses which was probably 80 percent of the Island,” says executive director Chris Culhane. “We had well over 1,000 volunteers over the couple of weeks of hurricane chaos and I think we went to over 500 houses.”

Chris Culhane is executive director of The Center of Anna Maria Island, which became a hub for storm recovery efforts.

The Center also became a distribution center for the truckloads of donations that rolled in from places as far away as Pittsburgh, Oklahoma and Wisconsin, as well as Sanibel Island which has its own harrowing hurricane history in the recent past. The kitchen at The Center was used to prepare meals for volunteers and for residents without functioning kitchens. Culhane wasn’t just thinking about the immediate impact of the storms—he was worried about the long-term financial ramifications for local hospitality workers who were out of work while the businesses they worked for were rebuilding. The Center puts on several concert events every year, so Culhane used his expertise to pull together a massive benefit concert in just three weeks. The Rock ‘N’ Support Concert was held at the Bradenton Area Convention Center on November 15, 2024 and featured headliners Lynyrd Skynyrd and special guest Marcus King. All proceeds went to two local nonprofit organizations (Shuckin’ Good Cause and The Center of Anna Maria Island’s Hurricane Relief Fund) who funded grants for displaced hospitality workers. “I went from hurricane chaos to concert chaos. Very different kinds of chaos,” Culhane says. “But we probably raised close to $400,000 to support all of the hospitality workers.”

Many of these hospitality workers are restaurant workers. For some restaurants, the future remains uncertain. For over 75 years, The Rod & Reel Pier has been an Anna Maria landmark. The pier sustained significant damage during Helene, but the two-story restaurant at the end was still intact. When Islanders woke up the morning after Milton though, they were greeted by a strange and sobering sight. Milton had completely destroyed The Rod & Reel, leaving behind only the pilings and the iconic sign. Owner Oliver “Oli” Lemke has been outspoken about his plans to rebuild, but zoning issues and the difficulties of insuring a new structure may make that a challenge.

Resilient restaurant owner Jason Suzor stands in front of The Waterfront Restaurant.

The Waterfront Restaurant is another eatery at the north end of the Island that suffered through severe damages. Owner Jason Suzor has experience rebuilding after a disaster. In 2004, just two years after his family purchased it, the original Waterfront building was almost completely destroyed in a fire and took almost nine months to reopen. Twenty years later, The Waterfront was flooded with as much as 4 1/2 feet of water in the back-to-back hurricanes, and clean-up was complicated by residue from the restaurant’s grease traps. Many of Suzor’s employees helped with the physical work of cleanup and assisted the contractors in an effort to hasten the reopening. Ultimately, The Waterfront was able to open its doors on December 3.

“I appreciate everyone’s support in the community,” Suzor says. “I’ve had so many people come by volunteering their time, just wanting to help out.” Suzor is one of several local business owners who shared their story of rebuilding with Island native Ben Webb. Webb started a YouTube channel in the aftermath of the hurricanes to give storm survivors a platform to give their personal accounts of recovery. It’s a topic that hits close to home for Webb—he is the owner of Anna Maria Island Dolphin Tours, a tour boat company that takes groups out to see dolphins and other natural wonders around Anna Maria Island and Egmont Key. “We’ve never been hit, and so you kind of live in denial,” Webb says. “And when it happens it’s just like, ‘Okay, what do I do to continue on?’”

Captain Ben Webb of Anna Maria Island Dolphin Tours interviewed residents about their personal recovery stories.

Webb has a house and two offices, and all three were destroyed by the hurricanes. But his biggest concern is the people who work for him who have now lost their way of making a living. In the weeks after the storm, the business was flooded with cancellations by visitors who were changing their vacation plans. The amount of refunds that had to be issued were crushing for a small business. Fortunately, Webb began to see a rebound in bookings in advance of Christmas and New Year’s and is optimistic that trend will continue. “Hopefully in March a lot more places are going to be open and we’ll be in good shape,” he says.

The Original Sand Dollar in Holmes Beach in the wake of the storms.

One of the first businesses to open on the Island was the Original Sand Dollar, a beach-themed boutique and gift shop that has been an Island staple since the 1960s. But just because it reopened relatively quickly, it doesn’t mean it didn’t take on its share of damage. “It was awful,” says owner Julia Duytschaver. “We probably had almost four feet of water through the whole store. We had floors that had actually bubbled up. It was bizarre. There were three broken windows from the water pressure. Things were floating everywhere.”

Duytschaver, her husband, some employees and even some volunteers rolled up their sleeves and got to work, spending ten hours a day cleaning up the store. They took out the wood floors and left the concrete exposed. Duytschaver’s husband put starfish on the floor and spray painted around them, creating a kind of negative space pattern. She took advantage of what she calls a forced remodel to make some big changes she had been thinking about anyway, like building new fitting rooms and changing the store’s layout. It’s a sweet reward after a lot of hard work. But that work isn’t done.

“In a lot of ways this has pulled people together, especially business owners,” Duytschaver says. “We’ve been so purposeful about getting lunch or patronizing the local places that are open. We always want to shop local anyway, but now we’ve all really banded together. It’s not a competition. We all help each other.”

Phtography by Wyatt Kostygan and Wes Roberts