Gulf boulevard bars with live music in Madeira Beach, Florida

Located at 14995 Gulf Boulevard in Madeira Beach, Florida, the Daiquiri Shak Raw Bar & Grille is the perfect spot to cool off and enjoy a wide variety of frozen daiquiris. With over 15 different flavors to choose from, you're sure to find a favorite. In addition to their frozen drinks, the Daiquiri Shak also offers a delicious raw bar featuring fresh clams, oysters, shrimp, mussels, and more. Their unique take on wraps is a must-try, and their dinner entrees range from Twin Sirloins to Caribbean Mahi and everything in between.

Located at 14080 Gulf Boulevard in Madeira Beach, Florida, Caddy's is the perfect spot for waterfront dining. Enjoy stunning sunset views while indulging in a menu filled with delicious food and drinks in a welcoming, family-friendly atmosphere. Open seven days a week, Caddy's offers a diverse selection of dishes and beach-inspired frozen drinks to satisfy both locals and tourists alike. With its tropical scenery, friendly staff, and flavorful cuisine, Caddy's Madeira Beach is a must-visit destination for anyone looking to experience the best of beachfront dining in Florida.

Bula Kava Bar & Coffee House (Bula on the Beach) is a unique institution located at 14601 Gulf Boulevard in Madeira Beach, Florida. As a bar, cafe, food, and store all in one, we offer a diverse range of quality products for our customers to enjoy. Our Kava is sourced from the best dried Kava grown in the Vanuatu and Solomon islands, by selected farmers who use traditional and organic methods. The Kava plant has a rich history, with its origins traced back to Vanuatu where it is cultivated in volcanic soil. The botanists Lebot, Merlin, and Lindstrom discovered that Vanuatu has the largest varieties of Kava, with some strains being more potent than others.

Caddy's Treasure Island is a waterfront restaurant located at 9000 West Gulf Boulevard in Treasure Island, Florida. This institution offers the best happy hour specials along Florida's Gulf Coast, with locations in Clearwater, Tampa Bay, Bradenton, Madeira Beach, John's Pass, and Indian Shores. Guests can enjoy drink specials and live music Sunset Sessions at all locations. Caddy's also has a rewards program where you can earn points for every $1 spent. The menu features seasonal food highlighting the best in seafood and American cuisine. Book a private beach cabana for your next event and check out the cocktail of the month and other drink promotions. Come grab a drink, feel the beat, and enjoy the beautiful waterfront views at Caddy's Treasure Island.

Welcome to John's Pass, the ultimate destination for relaxation and entertainment located at 14300 Gulf Boulevard, Madeira Beach, Florida. Nestled in the heart of this vibrant coastal community, our bar offers a perfect blend of laid-back charm and lively atmosphere, making it the ideal spot for locals and visitors alike. At John's Pass, we pride ourselves on our extensive selection of craft beers, expertly mixed cocktails, and a curated wine list that caters to all tastes. Our friendly and knowledgeable staff are always on hand to recommend the perfect drink to complement your mood or meal.