A novel strategy to assess the main variables that potentially affect the migration of antimony from PET bottles to beverages, including mineral waters and juices, is herein proposed. In a preliminary step, an LC-ICP-MS method previously used for water analysis was optimized to correct identify Sb species present in the studied matrices using HRMS. Subsequently, the influence of temperature and storage time up to 30 days on Sb migration from PET bottles into peach and pineapple juices of the same brand was studied. Storing PET bottled drinks at elevated temperatures (i.e., in a hot car or in summer) can cause antimony migration to exceed the limits allowed in the EU or USA. Because the behavior observed differed from the results reported for Sb migration in mineral waters, a second approach was proposed: three mineral water and two juice samples were kept in different PET containers and stored at an elevated temperature (up to 60 °C) to understand the role of the PET type and matrix simultaneously. This study demonstrated that both matrix characteristics and type of PET bottle greatly influence antimony leaching, highlighting the need to consider these variables together when conducting migration experiments. The obtained results can be helpful for developing future legislation concerning migration of pollutants from packing to food commodities.