The mesoscale variability in the Caribbean Sea is dominated by anticyclonic eddies that are formed in the eastern part of the basin. These anticyclones intensify on their path westward while they pass the coastal upwelling region along the Venezuelan and Colombian coast. In this study, we used a regional model to show that this westward intensification of Caribbean anticyclones is steered by the advection of cold upwelling filaments. Following the thermal wind balance, the increased horizontal density gradients result in an increase in the vertical shear of the anticyclones and in their westward intensification. To assess the impact of variations in upwelling on the anticyclones, several simulations were performed in which the northward Ekman transport (and thus the upwelling strength) is altered. As expected, stronger (weaker) upwelling is associated with stronger (weaker) offshore cooling and a stronger (weaker) westward intensification of the anticyclones. Moreover, the simulations with weaker upwelling show farther advection of the Amazon and Orinoco River plumes into the basin. As a result, in these simulations the horizontal density gradients were predominantly set by horizontal salinity gradients. The importance of the horizontal density gradients driven by temperature, which are associated with the upwelling, increased with increasing upwelling strength. The results of this study highlight that both upwelling and the advection of the river plumes affect the life cycle of mesoscale eddies in the Caribbean Sea.