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During the wintertime, easterly (E) to southeasterly (SE) flow in the Hawaiian coastal waters is frequent. These wind regimes alter the location and magnitude of channel and tip jet accelerations and the orientation and horizontal extent of the wake zones from east-northeast (ENE) trade wind conditions. The differences are the result of changes in orographic blocking by the Big Island and Maui, with respect to the prevailing wind. During an E wind event, the fastest winds over the ‘Alenuihāhā Channel (>9 m s⁻¹) occur in the channel exit with sinking of the inversion, which rises again downstream. Although the upstream wind speed is similar to typical summer ENE trade winds (7–8 m s⁻¹), the maximum channel wind speed is 3–4 m s⁻¹slower in the exit. The SE flow is characterized by maximum (~6 m s⁻¹) northeasterly (NE) channel winds along Maui’s south shore and at the channel exit. These winds are the result of orographic blocking on the eastern end of Maui as the northwestern tail of a tip jet off the northeastern coast of the Big Island impinges on Mount Haleakalā. Channel wind speeds are modulated by the speed and direction of this tip jet, which itself varies diurnally and throughout the approach of a midlatitude cold front. Removal of the Big Island shows how the tip jet speed and orientation modulate the pressure gradients and winds in the ‘Alenuihāhā Channel. Removal of the Maui County terrain reveals the impact of orographic blocking on the occurrence of channel winds off Maui’s south shore.