This 38-page monograph delves into the origins of the planing sailboat, from the discovery of the uses of hydrodynamic lift in the early 19th century to the shapes evolving today. I prepared it with help from an international group of sailors and naval architects, and I welcome further input for possible future revisions of the text. The only illustrations not done by me are at least a century old. I leave to others the granular histories of various racing sailboat classes, and attempt only to trace the history of planing sailboats as a type -- the ideas behind them and the evolving understanding of what makes them fast.