Breakup of the near-continuous winter sea ice into discrete summer ice floes is an important transition that dictates the evolution and fate of the marginal ice zone (MIZ) of the Arctic Ocean. During the winter of 2014, more than 50 autonomous drifting buoys were deployed in four separate clusters on the sea ice in the Beaufort Sea, as part of the Office of Naval Research MIZ program. These systems measured the ocean-ice-atmosphere properties at their location whilst the sea ice parameters in the surrounding area of these buoy clusters were continuously monitored by satellite TerraSAR-X Synthetic Aperture Radar. This approach provided a unique Lagrangian view of the winter-to-summer transition of sea ice breakup and floe size distribution at each cluster between March and August. The results show the critical timings of a) temporary breakup of winter sea ice coinciding with strong wind events and b) spring breakup (during surface melt, melt ponding and drainage) leading to distinctive summer ice floes. Importantly our results suggest that summer sea ice floe distribution is potentially affected by the state of winter sea ice, including the composition and fracturing (caused by deformation events) of winter sea ice, and that substantial mid-summer breakup of sea ice floes is likely linked to the timing of thermodynamic melt of sea ice in the area. As the rate of deformation and thermodynamic melt of sea ice has been increasing in the MIZ in the Beaufort Sea, our results suggest that these elevated factors would promote faster and more enhanced breakup of sea ice, leading to a higher melt rate of sea ice and thus a more rapid advance of the summer MIZ.