Used Highlander Sailboats for Sale

The Highlander is a distinguished 20-foot one-design sailboat, renowned for its lively performance and suitability for both competitive racing and comfortable family day sailing. Conceived by the celebrated designer Gordon "Sandy" Douglass, the Highlander quickly established itself as a versatile and enduring presence in the sailing community. It embodies a blend of speed and stability, making it an approachable yet exciting boat for a wide range of sailors. Built by Douglass & McLeod, a company synonymous with quality plywood and later fiberglass construction, the Highlander represents a significant chapter in American small boat sailing history.