We report analyses of marine and terrestrial proxies from IODP Site 339-U1385 on the southern Portuguese Margin. We focus on two time-windows, representing distinct climatic contexts: one from the Early Pleistocene interval of 41-kyr glacial cycles (1335-1385 ka) and one from the Early–Middle Pleistocene Transition (~1110-1200 ka). Analyses were undertaken with respect to (i) oxygen isotopic composition of planktic and benthic foraminifera, reflecting changes in surface-water conditions, and global ice-volume and deep-water hydrography, respectively; (ii) the relative composition of C37 unsaturated alkenones, reflecting surface-water conditions; (iii) pollen content, providing an integrated picture of regional vegetation changes in southwestern Portugal; and (iv) X-ray fluorescence (XRF) sediment composition changes, reflecting variations in the relative proportion of detrital (Zr) and biogenic (Sr) sediment supply.