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  • Writer's pictureLisa Codianne Fowler

Anna Maria Island

Miles Away but Worlds Apart

By Lisa Codianne Fowler

The sand feels silky and cool between my bare toes. I’m sipping a chilled mimosa while gazing upon the sugary strands of the beach. Bopping to cool jazz on a warm day at Anna Maria Island, I’m lovin’ this gulf-front table at The Sandbar restaurant. They call it Sunday Jazz Brunch. I call it heaven.

What’s Old is New Again

The Sandbar started out in 1911 as The Bathhouse, where visitors would spend the day at the beach and use The Bathhouse lockers to store their belongings. During World War II a fire nearly destroyed the building, and it was converted into army barracks. Today The Sandbar is a favorite beachfront eatery and top venue for weddings and events. Having undergone multiple remodels, it lovingly preserves, protects and honors the history of Anna Maria Island.

The island, though far from its colorful days of bootlegging, speak easies, and houses of ill repute, remains refreshingly eccentric. An hour’s drive from Tampa, this laid-back paradise is where Key West meets Caribbean.

Powder white sand, sparkling gulf waters, and sunsets in tropical technicolor… these are the main reasons that people flock to this barrier island. Perched between the turquoise waters of the Gulf of Mexico and peninsular Florida, it’s the ideal spot to fish for grouper, catch a beer at a tiki bar or simply unwind and celebrate the sunset. Parasail, kayak, play mini golf, tour the area by bicycle, the world of outdoor recreation is your oyster. Come for a day or stay for several for a true taste of island flavor.

Cool Digs

Anna Maria Island is replete with boutique properties, from seaside cottages to quaint B&Bs. Many are members of the prestigious Small Superior Lodging Association, including the Harrington House Bed & Breakfast, a romantic favorite smack on the beach. Anna Maria Guest Houses proffers properties on Pine Avenue, “The Greenest Little Main Street in America”, just steps away from its namesake’s fun and funky shops and the island’s seaside splendor.

What you won’t see are high rises. The structures are limited in height to no more than three stories. So if you’re looking for a suite on the 20th floor, you won’t find it here. But if your idea of paradise is nature at its laid-back finest, there is no better place to experience it than Anna Maria Island.

Village Charm

Though the island is just seven miles long, it is comprised of three celebrated communities: Bradenton Beach, Holmes Beach and Anna Maria. You can easily experience them all by taking the hop-on, hop-off trolley from one end of the island to the other. It runs every 20 minutes from 6 a.m. until 10 p.m., and it’s free.

Historic Bridge Street in Bradenton Beach hosts a quirky jumble of cafes, galleries and shops where you will discover unique gifts, jewelry, home décor and beach-inspired fashions. You’ll want to stop into the Blue Marlin, housed in a hard-to-miss bright blue 1920’s cottage. This cozy enclave specializes in fresh seafood and hearty fare, and features wines from smaller vineyards. On the weekends, the owner kicks it up a notch with live music from prominent local bands in their shaded courtyard.

The city is also home to the Bradenton Beach City Pier, a scenic spot for fishing and the site of the original bridge connecting Anna Maria Island to the mainland. Longboat Pass at the southern tip of the Island is a favorite haunt of boaters and anglers. Its fish-fertile waters host flounder; snook; sheepshead; sailfish, redfish – and from spring through fall – the mighty silver king. During the week, the area is a peaceful haven. But weekends, it’s party time. Dock together, boat hop, turn up the tunes and eat, drink and dance until the fiery sun slips behind the horizon.

There’s No Place Like Holmes

The community of Holmes Beach occupies the middle of the island at its widest point, and boasts three miles of beautiful beach where fishing, birding and water sports top the list of year round activities. As a commercial center, it has a mix of residential homes, condominium developments and businesses, all working in harmony with the island’s small town heritage. Restaurants, shops and art galleries are scattered throughout the town.

Down on Main Street

The north end of Anna Maria Island holds its own allure, the city of Anna Maria. From historic Anna Maria City Pier, the number one tourist attraction in Manatee County, it’s a ten-minute walk to the Rod and Reel, a lively family restaurant on another great fishing pier. Explore Pine Avenue, the city’s “Main Street”, unlike any other. Years ago the big draws were the General Store, bait shop, and jail – where wives purportedly sent their husbands when they came home inebriated.

More recently, partners Ed Chiles, Mike Coleman and Ted LaRoche purchased the majority of remaining lots to ensure the integrity of the city’s Old Florida ambience. Using reclaimed wood and natural landscaping, picturesque period cottages were designed, now an eclectic mix of locally-owned and operated shops and galleries. The Anna Maria Olive Oil Outpost is a culinary treat; find fresh-baked designer donuts at The Donut Experiment - owned by a retired policeman – and boutiques such as The Shiny Fish and Island Cabana offer whimsical island-themed gifts. Beach Bums is “your friendly neighborhood rental shop” where you can rent everything from beach cruisers and baby trailers to golf carts and kayaks.

All That Jazz

Sea breezes, the sound of the waves, seafood at its finest, live music, and, you're on the beach... so take that perfect snapshot. Don’t miss the Sunday Jazz Brunch at The Sandbar; tour the island, and have a delectable dinner with a side of spectacular sunset at The Beach House. As part of the Chiles Group, both feature locally-sourced, sustainable and heritage menu items, or what they term, “farm to fork; gulf to table; pasture to plate; crop to cocktail”. Savor that margarita and linger awhile. After the sunset, the stars illuminate the sky like diamonds on black velvet.

For more upscale dining, reserve a table at one of the most romantic and highest Zagat-rated restaurants in the country. At the intimate Beach Bistro, a panoramic sunset view sets the mood for an equally stunning meal.

Extraordinary Accolades

Anna Maria Island was chosen as the "#3 Prettiest City in the Country" by Forbes in 2013, one of the "Top 30 Islands in the World" by Condé Nast Traveler in 2014 and one of the "Top 10 Island Beaches for Perfect Sand" by Condé Nast Traveler in 2015. In addition to being a "TripAdvisor Traveler's Choice Destination Winner 2013 and 2014" it has also been proclaimed the "Top Family Vacation" spot in all of the US.

Kids, young marrieds, singles and seniors love it here. What’s not to love? Seagulls, dolphins… you know, dolphins are notorious for being sociable, friendly and smart. Of course they’re smart. They’re here, aren’t they?

If you go:

For more information on Anna Maria Island, or for help in planning your getaway, visit or call Bradenton Gulf Islands at 941-729-9177, ext. 231; Toll-Free 800-822-2017.

Cover of the Tampa Tribune/Tampa Bay Times 2015 Travel Florida section

Reprinted from The Tampa Tribune/Tampa Bay Times Annual Florida Travel Section 2015

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