The hurricane boundary layer (HBL) has been observed in great detail through aircraft investigations of tropical cyclones over the open ocean, but the coastal transition of the HBL has been less frequently observed. During the landfall of Hurricane Irene (2011), research and operational aircraft over water sampled the open ocean HBL simultaneously with ground-based research and operational Doppler radars onshore. The location of the radars afforded 13 hours of dual-Doppler analysis over the coastal region. Thus, the HBL from the coastal waterways, through the coastal transition, and onshore was observed in great detail for the first time. Three regimes of HBL structure were found. The outer bands were characterized by temporal perturbations of the HBL structure with attendant low-level wind maxima in the vicinity of rainbands. The inner core, in contrast, did not produce such perturbations, but did see a reduction of the height of the maximum wind and a more jet-like HBL wind profile. In the eyewall, a tangential wind maximum was observed within the HBL over water as in past studies and above the HBL onshore. However, the transition of the tangential wind maximum through the coastal transition showed that the maximum continued to reside in the HBL through 5 km inland, which has not been observed previously. It is shown that the adjustment of the HBL to the coastal surface roughness discontinuity does not immediately mix out the residual high momentum jet aloft. Thus, communities closest to the coast are likely to experience the strongest winds onshore prior to the complete adjustment of the HBL.