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Inclement weather putting a damper on your vacation, what are some fun unique things to do to make the most of your Anna Maria Island vacation even when a beach or pool day isn't an option!

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 know Halloween is a cherished holiday for families, and Anna Maria Island is the perfect place for spooky fun. Whether you’re staying in one of our luxury vacation rentals or exploring with little ghosts and goblins, discover the best trick-or-treat spots, festive island events, and tips to make your Halloween getaway on Anna Maria Island unforgettable.

Football season is here, and whether you’re an NFL fan, love college football, or just enjoy game day energy, Anna Maria Island has you covered. If you’re visiting and don’t want to miss the big game, check out the best Anna Maria Island sports bars and nearby hotspots. From cheering with locals to enjoying great food, cold drinks, and big screens, it’s the perfect way to catch every touchdown while soaking up island vibes.

While Anna Maria Island is known for its upscale dining and beachfront cafes, sometimes the best nights are found in local watering holes. That’s where the island’s dive bars on Anna Maria Island shine—offering cold drinks, live music, friendly crowds, and plenty of character. Perfect for visitors seeking a casual night out, these hidden gems deliver authentic island vibes without the frills, just fun and good company.

There’s nothing more romantic than a beach wedding on Anna Maria Island. With pristine white sands, turquoise Gulf waters, and breathtaking sunsets, it’s the perfect destination for your dream ceremony. Whether you envision a grand beachfront celebration or an intimate seaside gathering, Anna Maria Island offers stunning venues, luxury rentals, and a laid-back island charm for an unforgettable wedding experience.

Anna Maria Island is more than breathtaking beaches and sunsets—it’s also a shopper’s paradise. From chic boutiques and stylish beachwear shops to local markets with artisan goods, shopping on Anna Maria Island offers something for everyone. Whether you’re seeking unique souvenirs or island-inspired fashion, exploring the island’s shops is an essential part of your vacation experience.

Experience the magic of Anna Maria Island live music, where breathtaking beaches and unforgettable sunsets meet the perfect soundtrack. From laid-back acoustic sets with ocean views to lively nights dancing with local bands, AMI and nearby areas offer vibrant live music venues, bars, and restaurants for every mood. Discover why Anna Maria Island is the ideal destination for beach vibes, nightlife, and unforgettable entertainment.

Known for world-famous theme parks, pristine beaches, and endless sunshine, Florida is the ultimate vacation destination. Why choose between thrills and relaxation when you can enjoy both? Stay on the breathtaking shores of Anna Maria Island for a serene beach escape, then add adventure with nearby attractions like Disney World, Universal Studios, or Busch Gardens. Experience the best of both worlds—white-sand paradise and unforgettable theme park fun.

Discover the beauty and relaxation of Anna Maria Island, where white-sand beaches meet a laid-back island lifestyle. During your stay, treat yourself to top-rated salons offering expert haircuts, color, manicures, and pedicures. Whether you’re planning a romantic getaway or indulging in self-care, Anna Maria Island’s salons blend professional expertise with island charm—helping you look and feel your best in paradise.