Low-level regions of high wind speed known as tip jets have been identified near Cape Farewell, Greenland's southernmost point. These wind systems contribute to this area being the windiest location on the ocean's surface and play an important role in the regional weather and climate. Here we present the first analysis of the wind systems that make the Siberian coast of the northern Bering Sea the windiest location in the North Pacific Ocean during the boreal winter. In particular we show that tips jets characterized by enhanced northeasterly winds occur in the vicinity of the two prominent headlands along the coast, Cape Navarin and Cape Olyutorsky. The advance of sea ice in the region is shown to impact the frequency and location of the high speed winds in the vicinity of these two capes. Furthermore, we show that these jets are associated with the interaction of extra-tropical cyclones with the high topography of the Koryak Mountain range, situated just inland of the capes. The windstress imparted to the ocean via the tip jets is argued to help drive the formation of dense water in winter in the northern Bering Sea, thus playing an important role in the regional oceanic circulation.