2026 Best of Florida Regional Winner
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Dining & Nightlife


One of the best parts of any vacation is the food you eat, and there are plenty of absolutely fantastic restaurants right here on Anna Maria Island. The Island has French restaurants, Indian cuisine, adorable little cafes that serve acai bowls and sandwiches, and everything in between.


Family Fun on Anna Maria Island: Things to Do with Kids & Family Vacation Ideas

Some of the best family vacations aren't about packing every minute of the day with activities. They're about slowing down, spending time together and coming home with stories everyone still talks about years later. That's what makes Anna Maria Island such a wonderful destination for families. Seven miles of beautiful beaches giv...
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Holy Cow Ice Cream: A Sweet Stop in Holmes Beach on Anna Maria Island

Beach days and ice cream just seem to belong together. After an afternoon soaking up the sunshine on Anna Maria Island, few things hit the spot quite like a cold, sweet treat. If you're staying in Holmes Beach or exploring the middle of the island, Holy Cow Ice Cream & Other Cool Stuff is an easy place to add to your vacation ...
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Rainy Day Fun Near Anna Maria Island: Altitude Trampoline Park

A little rain doesn’t have to put a damper on your Anna Maria Island vacation. While sunshine, white-sand beaches and afternoons by the pool may be what brought you to the island, Florida weather occasionally has other plans. When an afternoon shower rolls in—or the kids simply need a break from another day at the beac...
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Back Alley Treasures on Anna Maria Island: Coffee, Local Art & Funky Finds

Historic Bridge Street in Bradenton Beach is known for its laid-back atmosphere, locally owned shops, restaurants and unmistakable Anna Maria Island personality. Tucked among it all is a colorful little spot where your morning coffee can easily turn into an afternoon of browsing. Back Alley Treasures is part coffee shop, part loca...
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Island Donut Company: A Sweet Stop in Bradenton Beach

There’s something about starting an Anna Maria Island morning with a fresh donut that just feels like vacation. If you're staying in Bradenton Beach or exploring the southern end of the island, Island Donut Company is an easy stop to add to your morning. Now located inside Island Scoops on Gulf Drive, visitors can pick up do...
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Vinny’s Italian Kitchen: Italian Food & Take-Home Meals on Anna Maria Island

You don’t have to leave Anna Maria Island to find a little taste of Italy. Tucked away in Holmes Beach, Vinny’s Italian Kitchen is part Italian kitchen, part pizzeria, part bakery and part specialty market. It's the kind of local spot where you can stop for pizza or pasta, pick up Italian groceries and desserts, or tak...
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October on Anna Maria Island: Spooky Events, Halloween, Ghost Tours & Fall Fun in 2026

Sunshine, white-sand beaches and turquoise Gulf waters may not be the first things that come to mind when you picture Halloween, but October brings a different kind of magic to Anna Maria Island. Fall is a wonderful time to visit Florida's Gulf Coast, with plenty of reasons to step away from the beach for an afternoon or evening. ...
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Labor Day Weekend on Anna Maria Island | 2026 Events & Things to Do

Labor Day weekend is the unofficial farewell to summer, and there may be no better place to enjoy one last long weekend by the water than Anna Maria Island, Florida. In 2026, Labor Day falls on Monday, September 7, giving visitors a three-day weekend to enjoy Anna Maria Island's white-sand beaches, warm Gulf waters, locally owned ...
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Best Sports Bars to Watch Football On and Near Anna Maria Island

Football season is officially back — and whether you're a devoted NFL fan, loyal to your college team, or just here for the wings and the energy, there's no better way to enjoy game day than in paradise. If you’re staying on beautiful Anna Maria Island, you’re in luck! The island and surrounding areas are packed w...
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