Projections of grapevine phenophases under future climate change scenarios are strategic decision support tools for viticulturists and wine producers. Several phenological models are tested for budburst, flowering, and veraison and for two main grapevine varieties (cv. Touriga Franca and Touriga Nacional) growing in the Douro Demarcated Region. Four forcing models (Growing degree-days, Richardson, Sigmoid, and Wang) and three dormancy models (Bidabe, Smoothed Utah and Chuine), with different parameterizations and combinations, are used. New datasets, combing phenology with weather station data, widespread over the Douro wine region, were used for this purpose. The eight best performing models and parameterizations were selected for each phenophase and variety, based on performance metrics. For both cultivars, results revealed moderate performances (0.4 < R2 < 0.7) for budburst, while high performances (R2 > 0.7) were found for flowering and veraison, particularly when Growing degree-days or Sigmoid models are used, respectively. Climate change projections were based on a two-member climate model ensemble from the EURO-CORDEX project under RCP4.5. Projections depicted an anticipation of phenophase timings by 6, 8 or 10–12 days until the end of the century for budburst, flowering, and veraison, respectively. The inter-model variability is of approximately 2–4 days for flowering and veraison and 4–6 days for budburst. These results establish grounds for the implementation of a decision support system for monitoring and short-term prediction of grapevine phenology, thus promoting a more efficient viticulture.