Since 2011, Sargassum seaweed has spread widely outside the Sargasso Sea, causing massive strandings on the coasts of the West Indies and Mexico, causing serious economic, ecological, and health problems. This Atlantic pelagic alga has the characteristic of moving in rafts. According to in situ observations, their size and shape can vary with the wind. To better understand the effect of wind on Sargassum coverage and aggregation size, we conducted a large temporal (2019–2022) and spatial scale study in the West Indies using OLCI/Sentinel-3 satellite imagery. During this period, a database of nearly 1 million Sentinel-3 aggregations, including their geometric and wind characteristics, was established. Analysis of the size distribution showed that wind has a dual effect on disaggregation and agglomeration depending on wind speed and aggregation size: (1) low winds favor agglomeration for the smallest aggregations and disaggregation for the largest aggregations; (2) high winds favor disaggregation for all aggregation sizes. In addition, topography also plays a role in size distribution: the Caribbean arc favors agglomeration over offshore zones, and coastal areas favor disaggregation over offshore zones.