Day Trips to Anna Maria Island

Anna Maria Island is only 55 miles from downtown Tampa, but it feels like a world away. As soon as you cross over the bridge onto the barrier island, you are transported to a bygone era when beach towns weren’t crammed with large chain stores and mammoth beach hotels and condos.

“There are no high-rises,” Chamber of Commerce President Terri Kinder points out; building-height restrictions were written into the island’s charter and contribute to the easygoing, Old Florida feel. We hopped on the Anna Maria Island Trolley to explore the three cities that make up the island and discovered why locals plant roots here that run decades deep and why visitors return again and again.

Bradenton Beach

Our first stop— the huge public beach at the southern tip of the island: Coquina Beach. A beautiful canopy of Australian pine trees lines the walkway between the parking lot and the dunes. We spot a couple enjoying a quiet stroll under the shade of the majestic trees and a mom lugging beach chairs as her kids run to the sand. Stepping onto the beach, we stumble upon a scene straight out of a postcard: soft, white sand set against turquoise water and a bright sky. It quickly becomes clear that the star attraction on this island is the beaches. Also home of the famous Coquina Beach Market.

Cove Bradenton Beach

Our next stop is Historic Bridge Street, a small, rustic commercial area. Idyllic scenes abound: lunch goers dining under an old oak tree overlooking the marina; kids watching dolphins from the pier; families golfing together at a small, eclectic mini-course tucked away behind the shops; and shoppers exploring quaint boutiques. At Cove, a smiling baby commands our attention. She is the daughter of store owner Kelly Headley, a proud island native. Her shop, she tells us, is a place to showcase “all the talent here.” She sells original artwork, handmade candles and soaps, and artisan jewelry made by fellow locals.

Gulf Drive Cafe

Continuing on Gulf Drive, we see restaurant after restaurant on the side of the road, all of them right on the beach. Two gigantic chickee huts are home to Gulf Drive Cafe, where it takes us less than 15 seconds to walk from a table to the water’s edge. One of the most famous restaurants in Florida also sits on the beach here on Anna Maria Island. Zagat-rated Beach Bistro is in Holmes Beach, where we head next.

Holmes Beach

A long residential stretch leads us into Holmes Beach in the middle of the island. We soon discover that most of the businesses are unique, mom-and-pop shops with stories that share a theme that has by now become familiar: setting up shop on the island decades ago and never leaving. Jim Brady moved here from Texas and opened West Coast Surf Shop in 1964. A recent fire could have shuttered the 55-year-old store, but in this town where neighbors help neighbors, the community rallied to raise money. The shop is now back open for business and proudly holds the title of the oldest surf shop in the state.

Duffy’s Tavern

Next, we visit another island staple, Duffy’s Tavern—owned and operated for more than 40 years by a former town mayor. Almost everyone is wearing a bathing suit and flip-flops and eating a burger—the restaurant’s claim to fame. Jimmy Buffett comes to mind among all the cheeseburgers in paradise.

City of Anna Maria

Reaching the northern end of the island a few hours before sunset proves to be fortuitous. It’s the perfect place to wind down after an action-packed day. We are struck by the southern charm of Pine Avenue, where boutiques and restaurants are housed in stately buildings with inviting verandas.

Poppo’s Taqueria and The Donut Experiment

The front porch that Poppo’s Taqueria shares with The Donut Experiment is packed with people enjoying ancho chicken tacos or donuts topped with Fruity Pebbles. Watching families bike and shoppers stroll, it feels like a movie scene.

Sandbar

For a must-see view of the sunset, we are told to head to the beachfront Sandbar restaurant. They don’t take reservations, and you could wait more than an hour, but you can spend it on the sand. Ending the day where we began—on the beach—and watching the sun go down over the Gulf of Mexico, we are struck by how fortunate we are to live in this part of the state. At this moment, we fully grasp the lure of Anna Maria Island and why a visit here should come with a warning: You may never want to leave.