The paper presents results from a study examining the relationship between large-scale modes of climate variability with the fluctuations in the yield of barley, durum wheat, olives and sunflower crops in Tuscany, Italy. In particular, the blocking circulation over the growing season, with associated hot and dry conditions, decreased yield for olive crops, barley and durum wheat. The teleconnections analysed in this study are the winter North Atlantic Oscillation (NAO) and the Summer North Atlantic Oscillation (SNAO); the West African Monsoon (WAM) and the Intertropical Front (ITF); and although NAO, SNAO, ITF and WAM are not strictly related to each other, the values of these indices are strongly related to the atmospheric circulation regimes and related weather types. Thus, they have an impact on precipitation and temperature patterns in Italy and on yields of important crops in Tuscany. Results show that the large-scale temperate and tropical variability directly influences the crop yield through three main circulation regimes. These patterns illustrate the importance of the large-scale modes, which, together with the associated weather types, have an impact directly on Tuscan crop yields; both barley and olive yields decline significantly when the ITF is further north with warmer and drier conditions in Italy.