This study investigates the impact of geographic location on birch and grass pollen seasons in Akureyri, Iceland, and Kraków, Poland, during the years 1998–2023 highlighting the significant variations in pollen dynamics due to differing climatic conditions. Wind-dispersed (anemophilous) pollen is not only crucial for plant reproduction but also a prominent trigger for allergic diseases affecting a large portion of the global population. We analyzed atmospheric pollen concentrations alongside meteorological variables to assess the timing, duration, and intensity of pollen seasons in both locations over the period 1998–2023. Results indicate that birch pollen seasons are more sensitive to meteorological factors, including temperature and precipitation, than grass pollen seasons. In Akureyri, both birch and grass pollen seasons demonstrate greater responsiveness to environmental changes, with complex interactions involving preceding weather conditions. In contrast, Kraków exhibits a more stable climate, with clearer correlations between meteorological variables and pollen production. This comparative analysis reveals that while Kraków grass pollen seasons are predominantly influenced by temperature, Akureyri dynamic weather leads to more variability in pollen season characteristics. Understanding these differences is essential for predicting future changes in pollen exposure and their implications for public health, particularly in light of climate change. Our findings emphasize the need for localized research to unravel the intricate relationships between geographic location, climate variability, and pollen season characteristics, providing valuable insights for managing allergic diseases related to pollen exposure.