The Pailolo Channel between Maui and Molokai is arguably one of the best downwind runs on Earth. The lines are so true, and the wind direction so consistent, it allows for one of the most radical open-ocean paddling adventures in the Hawaiian Islands. But lest we ever forget, those winds are a giant life force unto themselves that we cannot begin to control. They’re in charge.
To wit, more than a decade ago now, Pearl Jam icon Eddie Vedder—a lover of ocean play himself—was paddling the channel on a six-man sailing canoe when the craft ran into trouble and overturned. The team stayed with the overturned canoe for hours before a broken mast apparently allowed the traditional vessel to right itself. Half the crew was able to scamper aboard. But they did so without paddles, and the wind immediately shot the vessel downwind and quickly out of reach of Vedder and two female companions.