Fifty Three Fifty The Pourhouse – Holmes Beach Cafe on Anna Maria Island Nestled within the charming enclave of Holmes Beach on Anna Maria Island, Fifty Three Fifty The Pourhouse is a delightful local treasure that combines the best of both worlds. By day, it beckons as a warm and inviting cafe, and as the sun dips below the horizon, it transforms into a vibrant beer and wine bar. This versatile establishment, conveniently located at 5350 Gulf Drive, stands as a testament to the island's culinary diversity. At the heart of Fifty Three Fifty The Pourhouse lies its cafe persona, offering a range of culinary delights that speak to the essence of Holmes Beach. With an array of breakfast options, including the ever-popular Avocado Toast and the decadent Brown Sugar Banana French

Freckled Fin Irish Pub is your go-to destination for live entertainment in a lively and welcoming atmosphere. Located in the heart of the community, we host an array of talented musicians who cover a wide range of genres, from acoustic tunes to vibrant band performances. Our events are carefully selected to get you up and dancing, tapping your feet, and enjoying an evening of pure fun. Whether you're a fan of rock, roll, or soulful acoustics, our lineup is designed to impress and entertain. Come for the music, stay for the camaraderie, and don't miss out on a chance to win exciting prizes in our interactive trivia nights. Your evenings are promised to be filled with great tunes, refreshing drinks, and splendid company at Freckled Fin!

With its clean, Florida atmosphere meshed with traditional yet slightly modern dishes, Island Gourmet Grill is a fantastic choice for dinner with friends or a romantic date with a loved one, and the service and visually appealing atmosphere will surely entice guests to come back for more. Al Fresco dining is also available along with a full wine bar. Not only does Island Gourmet Grill offer a beautiful dining environment, but the cuisine is fantastic. Some modern Italian classics accompany array of fresh seafood, steak, chicken dishes and delicious hand made pizzas.