Category: The Delicious

The holiday season on Anna Maria Island is magical. With tropical charm, white-sand beaches, and stunning sunsets, the island becomes a festive paradise. Enjoy holiday boat parades, Christmas markets, and twinkling lights on Pine Avenue. Celebrate Christmas with local church services or ring in the New Year on the beach. From family gatherings to romantic getaways, Anna Maria Island is the perfect holiday destination.

At Once Upon A Beach, we believe fine dining is an essential part of every luxury vacation. That’s why we’ve curated a list of the top fine dining restaurants within 15 miles of Anna Maria Island. From elegant waterfront views to locally inspired gourmet cuisine, these handpicked dining destinations will elevate your island getaway and create unforgettable culinary experiences during your stay.

Anna Maria Island is renowned for its serene beaches, breathtaking sunsets, and charming small-town atmosphere—but it’s also a hub for exciting community events year-round. From lively parades and vibrant local markets to food, art, and music festivals, the island offers unforgettable experiences for visitors of all ages. No matter when you visit, Anna Maria Island promises something special to celebrate.

There’s something about starting your day on Anna Maria Island that makes every morning feel magical. Maybe it’s the soft ocean breeze, the sound of waves gently crashing, or the laid-back island vibe. Whether you're looking for a quick, casual bite or a more leisurely brunch experience, Anna Maria Island offers plenty of delicious options to kick off your day in paradise.

There’s nothing quite like indulging in a scoop (or two) of delicious, creamy ice cream on a warm, sunny day at the beach. Whether you’re looking for a classic cone, a refreshing frozen treat, or a decadent sundae, Anna Maria Island offers a variety of ice cream shops that are sure to satisfy your sweet tooth.