The Island Mass Effect has been primarily attributed to nutrient enhancement of waters surrounding oceanic islands due to physical processes, whereas the role of land runoff has seldom been considered. Land runoff can be particularly relevant in mountainous islands, highly susceptible to torrential rainfall that rapidly leads to flash floods. Madeira Island, located in the Northeast Atlantic Ocean, is historically known for its flash flood events, when steep streams transport high volumes of water and terrigenous material downstream. A 22-year analysis of satellite data revealed that a recent catastrophic flash flood (20 February 2010) was responsible for the most significant concentration of non-algal Suspended Particulate Matter (SPM) and Chlorophyll-a at the coast. In this context, our study aims to understand the impact of the February 2010 flash flood events on coastal waters, by assessing the impact of spatial and temporal variability of wind, precipitation, and river discharges. Two specific flash floods events are investigated in detail (2 and 20 February 2010), which coincided with northeasterly and southwesterly winds, respectively. Given the lack of in situ data documenting these events, a coupled air-sea-land numerical framework was used, including hydrological modeling. The dynamics of the modeled river plumes induced by flash floods were strongly influenced by the wind regimes subsequently affecting coastal circulation, which may help to explain the differences between observed SPM and Chlorophyll-a distributions. Model simulations showed that during northeasterly winds, coastal confinement of the buoyant river plume persisted on the island’s north coast, preventing offshore transport of SPM. This mechanism may have contributed to favorable conditions for phytoplankton growth, as captured by satellite-derived Chlorophyll-a in the northeastern coastal waters. On the island’s south coast, strong ocean currents generated in the eastern island flank promoted strong vertical shear, contributing to vertical mixing. During southwesterly winds, coastal confinement of the plume with strong vertical density gradient was observed on the south side. The switch to eastward winds spread the south river plume offshore, forming a filament of high Chlorophyll-a extending 70 km offshore. Our framework demonstrates a novel methodology to investigate ocean productivity around remote islands with sparse or absent field observations.