Against water, or against wind? Sailing against the wind feels fastest, because your SoG adds to the relative wind; but sailing downwind is much faster. The mo

Against water, or against wind? Sailing against the wind feels fastest, because your SoG adds to the relative wind; but sailing downwind is much faster. The more interesting part is that boats can actually sail faster than the wind that powers them! Depending on the surface, from 1.6 times the true wind speed in a catamaran on water, to 5 or more times the wind speed in an iceboat.