Anna Maria Island, a narrow, seven-mile-long strip south of Tampa Bay, used to be loved for what it lacked. Unlike most beach towns, AMI had no high-rises, almost no chain stores, and—until recently—no terrible hurricane damage.
Amanda Escobio Ryan has loved Anna Maria ever since she used to visit as a child. The licensed massage therapist moved there in 2006 after a difficult divorce—“it was a healing place for me, as it was for many people”—and opened her own bodywork business two years later. Working with the Silver Surf Gulf Beach Resort, Escobio Ryan refashioned a tiki hut into an oceanside treatment room, adding massage tables and privacy curtains.
By 2024 she was running two thriving spas at either end of the island and had to make hard decisions—including about hurricane insurance. “Buying the insurance premium would have been $15,000,” she says. “I didn’t pay it. I always said, ‘The day the hurricane comes, I’ll figure it out.’”
In the fall of 2024, two hurricanes came, and since then she and all the other islanders have been figuring it out: how to return, rebuild, and reconfigure their homes, businesses, and lives.
Hurricane Helene struck first; Escobio Ryan last saw her massage tiki hut in an aerial photograph, bobbing down the island’s flooded main street like a raft on a river. Days later Escobio Ryan returned by boat to determine what could be salvaged. A TV news crew found her sorting out soaked merchandise. Pushing wet hair out of her eyes, she said, “We’re strong, we’re salty, and we’re not going anywhere.”
Two weeks later Milton hit, putting the island under four feet of water—again. “Every building had a dumpster in front of it,” Escobio Ryan recalls. “Every swimming pool was filled with sand.”
Early this year, the salty air rang with grinding cement mixers and earth-moving equipment. “That’s the new soundtrack to the island,” Escobio Ryan says. “It used to be leaf blowers on weekends, and people would complain. Now it’s jackhammers, roofers pounding, and chainsaws, and it makes us smile. You can hear construction noise in the massage rooms, and I thought clients would be disturbed, but they say, ‘It’s good; it’s progress.’”
As that progress continues and Anna Maria welcomes back visitors, here are a few of Escobio Ryan’s highlights—both classic and newly built—on the island:
Beach Cruising
The best way to see the island, Escobio Ryan says, is by golf cart. On a recent sunny day she picked out a blue two-seater from the fleet at Robinhood Rentals. “It’s like being in a boat,” she says, “only on land! It’s open, you’re out there, and it even helps with parking. It just feels better.” Curls tucked under a sunhat, she steered toward the beach near Magnolia Avenue—her favorite. Facing the water on the short block are just four houses: sky blue, lemon yellow, and mint green. “I call these houses the ‘painted ladies’ because they’re a little bit like San Francisco, but they look out on this tropical beach.”
Nearby, Thrive Yoga & Fitness offers free (donations accepted) classes right on the sand near the Sandbar Restaurant, where visitors can drop in and downward-dog with the locals. Across the street in the old IGA is Ginny & Jane E’s, a combination café and artists’ showcase that is hugely popular with beachgoers; Escobio Ryan especially likes the homemade chips with ranch dressing.
Ode to Holmes Beach
In the middle of the island sits its largest town, Holmes Beach, home to Manatee Public Beach (one of the few with lifeguards). Escobio Ryan takes her kids to the Beach Cafe for all-you-can-eat pancakes on Sundays, or to dance on the sand on nights when Mike Sales performs. She’s also a fan of what she calls fake New Year’s Eve: “On December 31st at sunset, they claim it’s midnight and do a big countdown and then a big toast. And then everyone can go home and feel like they’ve celebrated.”
Across from the public beach is the beach shack Skinny’s Place, a fixture since 1952. “They’re the best burgers on the island,” Escobio Ryan says. “And you have to say you want a Fatty Burger!” Holmes Beach also houses one of the more glamorous places to stay on the island, the Bali Hai Resort. “Sometimes I get clients who want to splurge a little bit, and I’ll send them to Bali Hai. It’s special because their rooms open right onto the beach.”
For longer stays, Escobio Ryan sends people to the Silver Surf, three airy, bright buildings within sight and sound of the waves. “It has a private beach, with shade and chairs all set up, so it makes it really easy to stay there, especially with kids.”
Silver Surf also hosts Escobio Ryan’s new, purpose-built massage hut, which replaced the one that washed away; its thatched-roof “chickee” was done by a Seminole company according to an original Native design. “It’s more spacious, more airy, and more waterproof than the old tiki,” Escobio Ryan says. “It’s no longer a nightmare if we get caught in a downpour.”
Bradenton Beach and Bridge Street
At its southern end, in Bradenton Beach, the island narrows to less than half a mile wide between the Gulf of Mexico and Palma Sola Bay. In between is historic Bridge Street, host to the Sunday outdoor market, a mini golf course, and many locally owned shops. With stores open late and live music many nights, it’s the perfect place for a cocktail, appetizers, and souvenir shopping stroll, Escobio Ryan says. And if someone doesn’t want to drive after a day of sun and sipping, they can hop on the free, open-air Island Trolley.
This neighborhood also holds one of the island’s best attractions, a kind of treasure hunt. “Somewhere on Bridge Street,” Escobio Ryan says with an air of mystery, “is the Heart Rock of Anna Maria Island.”
In the middle of Bridge Street, Escobio Ryan’s Sea-Renity Spa and Eco Boutique offers beachy gifts as well as luxurious massages. Between clients, the massage therapists go to Island Time Bar & Grill for fresh-squeezed orange juice and to Back Alley for frozen lemonade. For a full meal, Escobio Ryan will visit the tiny café Pane E Amore. “I love the atmosphere, and it’s the best lasagna I’ve ever had. The owner is a wonderful Italian guy who loves to cook and talk to people.”
Finally, “for a big night out, I’d start at the Doctor’s Office [craft cocktail bar] and with a walk on the beach at sunset, then have dinner at the Bridge Street Bistro. I love their Caesar salad with fresh fish. Or for a fancier meal I’d head to SALT Bar & Table, and then get dessert on Longboat Key [the next island south] in the Haye Loft Lounge.”
Despite the destruction of the hurricanes and the ongoing changes, Anna Maria Island remains well loved. Its heart stone remains, a natural formation that anyone can find, a fitting symbol for an island that is solid, grounded, and shaped by storms and time.
