Experience the Vintage Charm of Anna Maria Island This Winter
Plan a trip to Anna Maria Island just up the coast from Tampa, FL.
"What a Florida postcard!” developer Will Bean must have thought over 100 years ago, seeing this seahorse-shaped, 7-mile-long barrier island with white sand washed by the sparkling waves of the Gulf of Mexico on the west and lapped by the deep blue bay waters to the east. It would be an irresistible escape for winter-weary Northerners, for folks fleeing yellow fever in Tampa just up the coast, and for anyone else who sought a ticket to paradise.
Inheriting the land from his father (Anna Maria Island’s first homesteader) in 1892, Bean worked with fellow promoter and developer Charles Roser to make the island into an escape ready for investment. With a knack for publicity, he even purchased exotic seashells to secretly scatter along the beaches every night so tourists would find them—and write home of this shell-seeker’s dream.
That meant a boom in the early 20th century: a cottage-lined main street leading to a long pier that welcomed steamship-borne travelers, and later tidy plats of cinder block-and-concrete houses for snowbirds and beach motels scattered like Monopoly properties along that gorgeous shore. And then that was it, really. While beaches to the north and south surged with high-rises in the seventies and later, Anna Maria Island tapped the brakes. So now, to arrive here in the 21st century is to greet that older landscape. It’s no wonder that folks who’ve caught on to the island’s quiet delights cling tightly to them.
Spend a few nights at Bamboo Apartments (which owner Alice Sutton’s grandparents built in 1971) or the 1916 beachfront cottage on the property, and you instantly hear the whisper of Old Florida. “My grandmother had one phone for the whole place,” Sutton says. “She’d run out to the beach to see if her guests wanted to take a call when it came in. They usually didn’t!” It’s easy to see why: With a small knoll of sand and sea oats breaking to a wide beach infused with western breezes and rolling waves, it still feels like Sutton has the only phone on the island. And there’s no need to take any calls, thank you.
Three towns dot Anna Maria Island’s length. Each requires slow driving (25 mph in most cases) and displays its wares with ready ease. At the north end sits the city of Anna Maria anchored by Pine Avenue, Bean’s original then-sand-and-seashell main street that bisects the island. Here, brightly painted restored homes and mercantile buildings from the original boom now hold charming markets, galleries, bakeries, museums, bike shops, restaurants, and (naturally) vacation-rental offices. At first glance so beautifully old-fashioned, this place offers some of the most decidedly on-trend spots: Poppo’s Taqueria, where they make tortillas by hand and have local kombucha and beer on draft; The Donut Experiment with wildly original combinations of toppings; and boutiques with of-the-moment clothing. In Anna Maria’s Historic Green Village is a group of old buildings retrofitted with solar panels and rainwater cisterns to become a net-zero community. It’s proof that you can live the Florida life—and even stay cool—without wasting resources.
While Pine Avenue hums with the old and the new simultaneously, just up the road, the island’s iconic circa-1950 Rod & Reel Pier holds onto a timeless now with its narrow, weathered dock leading to a double-decker building (with seafood above and a bar below),
And the wonders roll on. In Anna Maria’s slender midsection, the town of Holmes Beach is ground zero for ogling mid-century Florida homes and plying old-school souvenir shops and beach bars. Farther south, Bradenton Beach holds at its heart the short, fun-loving Bridge Street—a salty complement to Pine Avenue—with a tiny miniature golf course, seafood joints, waterfront bars with thatched tiki perches, and its own pier that culminates in a fine oyster house with views up and down the bay.
With dozens of short public pathways to get to the Anna Maria beaches, the choices seem almost dizzying—and they’re all fantastic. Pick the access closest to you, take an umbrella for shade, and occupy your slice of Gulf Coast paradise. Or spend a day at Anna Maria’s southern tip at Coquina Beach, famed for its wide stretches of sand and flanks of palms. Or make a pilgrimage at dusk to Bean Point at the north tip of the island to watch the sun drop into the Gulf while its waters play with the wavelets from Tampa Bay. See legions of terns hunker down, facing into the breeze in such a way that they look as if they’ve come to take in the sunset. Watch as a great blue heron arrives to stalk a shore fisherman who has left his bait unattended while he takes a dip in the peach-tinted waters. “What a Florida postcard!” you might think. And you wouldn’t be wrong.
Airports of choice: Tampa International Airport (TPA) and Sarasota Bradenton International Airport (SRQ)
Average February high: 74°F
Where to Eat
There’s no better breakfast on the island than at Ginny’s & Jane E’s, an eye-popping, warmhearted restaurant and marketplace in Anna Maria. Everything is cooked from scratch, the outsize cinnamon rolls are legend, and the shopping is irresistible. (Florida ornament for next Christmas? Check.) Also on the sweet side, Pine Avenue’s The Donut Experiment will layer your cakey confection with a variety of frostings and wild toppings (including Fruity Pebbles), and The Waffle Press plates smallish takeaway waffles with toppings like Key lime. Nearby, Poppo’s Taqueria does incredibly fresh tacos, quesadillas, bowls, and burritos. Then at happy hour, The Waterfront Restaurant near City Pier mixes the island’s best cocktails. For beach-bar-style fun, head straight for the Bridge Tender Inn in Bradenton Beach or The Ugly Grouper in Holmes Beach. Dinner-time at the Sandbar restaurant is a revelation: a toes-in-the-sand spot with a stunning sunset view of the Gulf along with topflight locally sourced seafood and more. (Its sister location, Beach House Restaurant in Bradenton Beach, offers similar pleasures.)
Where to Stay
In Holmes Beach, the Bamboo Apartments are an Old Florida treasure right on the sand and steps away from the island’s free trolley stop. Done up with vintage-style rattan and wicker, all five units are delights; the original 1916 duplex cottage lined in heart pine (including the ceiling and floors) is nostalgic perfection. Other motels bursting with charm include Cedar Cove Resort & Cottages, Haley’s Motel, Bungalow Beach Resort, and SeaSide Beach Resort.
Where to Shop
You can spend at least a day mining the goods in and around Pine Avenue. Look for Spartina 449 tunics and caftans at The Egret’s Nest, fun Draper James looks at Pink & Navy Boutique, and Lilly Pulitzer resort wear at The Island Cabana. The Studio at Gulf and Pine features local artists and has beautiful and affordable options. The Anna Maria General Store is an ideal spot to scout for treats from this area.
Where to Play
Morning yoga is offered year-round on Saturdays and Sundays at the Pine Avenue public beach access (voluntary contribution) and is a wonderful way to greet the day. Rent bikes and more gear for the week in Anna Maria at Beach Bums Island Attitude and Lazy Turtle Beach Rentals. They’ll set you up to get outside.