Enjoying Live Music on Anna Maria Island

You have a day of enjoying the beautiful beaches of Anna Maria Island. Or maybe you went exploring by bicycle. Either way, sunset is coming, and the question is: Now what? If you are a fan of live music, you are in luck because the island provides you with options. Here are a few of them.

Harry’s Grill

To call Harry’s Grill a local favorite would be an understatement. This cozy little spot was voted the Island’s favorite nightspot, band, bar and grill in 2017, 2019, 2020, 2021 and 2022 by readers of the Anna Maria Island Sun. It boasts a pet-friendly patio area that even has cornhole games available to occupy your time when you’re not eating or listening to the live music. Bonus: If your name is Harry or Harrietta, and you can prove it, you get one free draft beer of your choice. Harry’s is located at 9903 Gulf Drive Anna Maria, FL 34216. Check out their calendar of upcoming music events.

The Ugly Grouper

You can’t talk about the Ugly Grouper without talking about the statue in front of it. The massive sculpture is 20 feet long, 14 feet high and weighs in at 3,180 pounds. Made by Tampa Bay artists from used car parts, metal objects and even some road signs, this work of art lives up to its name in a funky and fun sort of way. The Ugly Grouper features live music seven days a week. Many days the music starts at noon and goes until 8:00 pm. You can find the live music schedule on their website. The Ugly Grouper is located at 5704 Marina Drive, Holmes Beach, FL.

Freckled Fin Irish Pub

The Freckled Fin calls itself a music hall and the schedule lives up to that. Live music is on tap almost every day and those few days without live music have a DJ. Some of those nights are karaoke nights, so if you want to channel your inner rocker or country crooner, the Freckled Fin may be just the ticket. The pub has one of the more diverse offerings of music in the area with different types of music and performers that mix in original songs with cover tunes. Check out their calendar or just take a chance and show up at 5337 Gulf Dr, Holmes Beach, FL 34217. Either way, you’re going to find music.

Island Time Bar and Grill

Located in the historic Bridge Street area, the Island Time Bar and Grill offers beautiful views of the Gulf of Mexico along with live music seven days a week. On weekdays, the music usually starts at 7:00 pm, but the party starts earlier on the weekends. Saturday and Sunday usually see two different acts, one starting at 1:00 pm and the second starting at 7:00 pm. You can check their calendar of events before you go.  Island Time Bar and Grill is located at 111 Gulf Dr. S Bradenton Beach, FL 34217. If you are also looking for a fine dining experience, check out the Bridge Street Bistro upstairs from the bar.

These are just a few of the places you can enjoy live music on Anna Maria Island. If you need more options, contact us and one of our local experts can give you some more options.