Category: The Boozy

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.

Whether you're enjoying a relaxing beach getaway or looking to sip cocktails while watching a spectacular sunset, there are plenty of bars and happy hour spots to explore. As the team behind Once Upon A Beach, your trusted luxury vacation rental agency, we're passionate about making sure our guests have the best island experience, from where to stay to where to play. Here's our ultimate guide to the best bars and happy hours on Anna Maria Island.

While the island is renowned for its pristine shoreline and relaxed atmosphere, it’s also home to a thriving local cocktail scene. Whether you’re winding down after a day in the sun or celebrating a special occasion, there’s no better way to indulge than by sipping a finely crafted cocktail made with fresh ingredients, bold flavors, and local flair.