Monitoring the main grapevine phenological stages is a key procedure for optimizing vineyard activities and improving yield and quality attributes. Remote sensing may be an effective and practical monitoring tool, as data from on-board satellite sensors can measure vegetative growth. In the current study, a 12-year time series of four main phenophases (budburst, flowering, veraison and harvest) were obtained from an experimental vineyard located in Lisbon (Portugal). LANDSAT surface reflectances were used to calculate the Enhanced Vegetation Index (EVI) and derived metrics. Both time series were then analysed. Results show statistically significant relationships between vegetation metrics and phenological timings and intervals, such as the linkage between the peak greenness and flowering/veraison. The current study highlights the applicability of remote sensing to monitor grapevine phenology in both retrospective and real-time, bringing an added-value to the winemaking sector.