The flowering phenology of six genetically distant strawberry cultivars (‘Candonga®’ (ES), ‘Clery’ (IT), ‘Florence’ (UK), ‘Frida’ (NO), ‘Gariguette’ (FR), and ‘Sonata’ (NL)) was studied for 3 years in relation to climatic parameters in open-field cultivation at three locations (Norway, Poland, Germany) and in soil-less cultivation at two locations (Italy, and France), covering a distance of 16 degrees of latitude. This proved to be a useful approach for unravelling the climatic adaptation and plasticity of strawberry genotypes and their suitability both for profitable cultivation and as a breeding pedigree. Despite the intercorrelated character of the climatic variables, the observed results highlight the importance of global radiation as a powerful modifying phenological factor in strawberry. Generally, early flower initiation was associated with elevated temperature and global radiation. ‘Frida’ revealed the highest dependency on global radiation for flower initiation, while ‘Sonata’ was least affected by temperature and radiation. In general, temperature and global radiation in periods both preceding and following flower initiation had a stronger positive effect on the number of flowers than on crowns, especially under open-field conditions. The influence of these factors was highly variable across the cultivars: ‘Clery’, ‘Florence’, and ‘Gariguette’ were most affected, while ‘Frida’ was least influenced.