The island used to be "blue-hair, and nothing was happening," Dutton says. Now, all ages swarm in, spawning more art galleries, festivals and last year's first bridal fair, where inns, caterers and photographers displayed their wares to woo engaged couples. (The Anna Maria Chamber of Commerce is promoting it as a Florida beach wedding capital and plans another fair Jan. 25).
As for residents, Anna Maria "draws a lot of talented, intelligent people," Dutton says. "It's a very special place. It has got a blessing on it."
On this Friday, a manatee swims lazily at Leffis Key nature preserve at the island's southern tip. A sand-castle-building competition is underway in Bradenton Beach. Near the island's midpoint, a group of white-haired women sit in white plastic chairs at the Cafe on the Beach to share weekly games of contract bridge and conversation.
That night at the Bridgetender Inn and Dockside Bar, a locals' hangout in Anna Maria's Bradenton Beach — the most commercial of three incorporated communities on the island — waitresses call visitors "hon" and "dear," and the couple at the neighboring table starts a conversation while a guitarist plays a white-bread version of reggae star Bob Marley's Stir It Up.
"We're very proud of our area," says Barbara Trivoli, a vivacious redhead sipping a Corona Light on the terrace overlooking a marina under a full moon. "We have a very safe environment here." She and her husband, George, a finance professor, live across from the island in Cortez, Fla., and often drive over to eat.
Indeed, the dining is as good as the fishing that lures many visitors. Options range from a simple grouper sandwich for $8.50 and a $6.95 pitcher of beer at the old Rod & Reel Pier, where you can cast a line, to the world-class, white-tablecloth Beach Bistro, where chef/owner Sean Murphy stirs up great reviews with a locally adored plum-tomato soup with Maytag blue cheese and risotto with truffle foie gras and mushrooms. He arrived three decades ago, not planning to stay, and he and his wife brought up two kids in a place "where everybody knows your name."
The bistro's clubby lounge, where photos of star patrons such as Robert De Niro and Ed Asner line wood-paneled walls, is a version of TV's Cheers bar. Bartender Fred Sullivan, 59, introduces a newcomer to patrons and recommends the succulent "White Castle Slider" — foie gras and prime beef on a sweet garlic bun with Béarnaise sauce. It's an affordable ($14) option on the $30-plus entree menu.
Down the bar, retired St. Louis banker Terry Schaeffer, like many here, came down for a vacation, and he and his wife ended up buying a home.
"The natural beauty attracted us, and we fell in love with it," he says. "It's not the land of excitement" — there are some party bars with live bands, such as D. Coy Ducks, but the sidewalks tend to roll up early.
Those expecting vacation manses are surprised. Anna Maria doesn't look fancy ."There's a lot of money here, but it's 'quiet money,' " bartender Sullivan says.
The dearth of gated estates and streets lined with unassuming homes with carports don't signal affluence. A free trolley ferries visitors up and down Gulf Drive. You can lease digs near the beach for $1,000 a week in high season — especially with more "for rent" signs dotting lawns this year.