Category: The Boozy

Football season is always an exciting time, whether you're a passionate NFL fan, following college football, or simply enjoying the camaraderie and excitement of game day. If you're visiting or staying on Anna Maria Island and don’t want to miss out on the big game, you’re in luck. The island and its nearby areas offer a variety of lively sports bars where you can cheer for your favorite team, enjoy great food, and catch all the action on the big screen.

While Anna Maria Island offers plenty of upscale dining options and beachfront cafes, sometimes all you want is a cold drink, good company, and a no-frills environment. That’s where Anna Maria Island’s dive bars come in. These local watering holes are perfect for anyone looking for a casual, fun night out with a little grit and plenty of character.

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.