One of the few beachfront bars anywhere on the Gulf Coast where you can legally wiggle your toes in the water while holding your drink, Caddy’s on Treasure Island is a Gulf Coast legend. The panoramic views from the open-air second floor are some of the best on any beach in Pinellas County — watch the Treasure Island sunset crowd gather on the sand every evening from a vantage point that feels like you’re floating above it. BBQ, daily live music, and cold drinks from open to close keep the energy consistently high. It can get rowdy on weekends, which is either a feature or a warning depending on your preference.
