Experience the Vintage Charm of Anna Maria Island

Preserving the landscape and architecture of the past, Anna Maria Island resisted building high-rises like beaches to the north and south. This island's quiet delights attract new visitors while locals cherish its pristine scenery.

"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 sands, surrounded by the sparkling Gulf of Mexico on the west and the deep blue bay waters to the east. It is an irresistible escape for winter-weary Northerners and anyone who wants a ticket to paradise.

History of Anna Maria Island

Inheriting the land from his father (Anna Maria Island's first homesteader) in 1892, Will Bean worked with fellow promoter and developer Charles Roser to make the island an escape ready appealing to investors. 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 boasting this shell-seeking destination.

A cottage-lined main street led to a long pier, welcoming steamship-borne travelers. Later tidy plats of cinder block-and-concrete houses for snowbirds and beach motels scattered Anna Maria Island as new properties developed along the gorgeous shore.

Areas of Anna Maria Island

Pine Avenue

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 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.

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 its timeless, weathered dock leading to a double-decker building (with seafood above and a bar below),

Holmes Beach

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 the short, fun-loving Bridge Street at its heart—a salty complement to Pine Avenue. A tiny miniature golf course, seafood joints, waterfront bars with thatched tiki perches, and a pier culminate 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. Spend a day at Anna Maria's southern tip at Coquina Beach, famed for its vast stretches of sand and flanks of palms. Make a pilgrimage at dusk to Bean Point at the north tip of the island to watch the sun drop into the Gulf.

Historic Green Village

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.

Where to Eat

After the first glance, this beautifully old-fashioned place offers some of the most decidedly modern spots.

For Breakfast

A breakfast, or any time of day, treat is the wild original topping combinations at The Donut Experiment. Some featured donuts include Key Lime and Sriracha made with peanut butter, peanuts, and a sriracha drizzle. The Pine Avenue shop will layer your cakey confection with various frostings and wild toppings (including Fruity Pebbles).

There's no better breakfast on the island than at Ginny's & Jane E's, an eye-popping, warmhearted restaurant and marketplace. The food, cooked from scratch, is outmatched only by the legendary oversized cinnamon rolls.

For small takeaway plates, try The Waffle Press. This breakfast spot tops its breakfast creations with classic Key Lime.

For Happy Hour

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.

For Dinner

Dinner at the Sandbar restaurant is a revelation. It's a toes-in-the-sand spot with a stunning sunset view of the Gulf and locally sourced seafood. (Its sister location, Beach House Restaurant in Bradenton Beach, offers similar delights.)

The Mexican-inspired restaurant, Poppo's Taqueria, makes tortillas by hand for fresh tacos, quesadillas, and burritos and has local kombucha and beer on draft.

Where to Stay

In Holmes Beach, spend a few nights at Bamboo Apartments (which owner Alice Sutton's grandparents constructed 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 into 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.

It's an Old Florida treasure 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, andBungalow Beach Resort.

Where to Explore

Shopping

You can spend a day (at least) mining the goods in and around Pine Avenue. Look for Spartina 449 tunics at The Egret's Nest and Lilly Pulitzer resort wear at The Island Cabana.

The Studio at Gulf and Pine has beautiful and affordable options to explore local artists. The Anna Maria General Store is an ideal spot to stock up on treats from the area.

For Outdoor Activities

Morning yoga is offered year-round on Saturdays and Sundays at the Pine Avenue public beach access (voluntary contribution) and is a beautiful 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.