Phenological, aerobiological, and weather data are useful tools to study local and regional flowering dynamics in crops with economic importance. The present study focuses on four autochthonous grapevine cultivars, namely, ‘Treixadura’, ‘Godello’, ‘Loureira’, and ‘Albariño’ (Vitis vinifera L.), which belong to the Designation of Origin Ribeiro area (located in northwestern Spain) from 2015–2019. The aims of the work were to (1) compare the airborne pollen concentration in the vineyard collected by two different traps, (2) analyze the influence of the main meteorological variables on cultivar phenology and pollen concentration, and (3) test the contribution of the air masses on pollen concentrations in the vineyard. Phenological development has been assessed twice weekly, according to the Biologische Bundesanstalt, Bundessortenamt und Chemische Industrie (BBCH) scale. Airborne pollen concentrations were monitored by using two traps during stage 6 (flowering), namely, a Hirst volumetric sampler and a Cour passive trap. The bioclimatic conditions affected the duration of flowering, ranging from 11 and 24 days. The highest seasonal pollen integral (SPIn) was registered in 2016 for the Hirst sampler, with 302 pollen, and in 2019 for the Cour trap, with 1,797,765 pollen/m2/day. The main variables affecting pollen concentrations were average temperature during the main pollen season, as well as, temperatures and dew points during the pre-peak period. The relationship between pollen data registered by both traps and the obtained harvest indicate that the Hirst trap may be more suitable for predicting a local production and that the Cour sampler is more appropriate for forecasting regional productions.