Over the last decade, several events such as Sailbot, World Robotic Sailing Championship and the International Robotic Sailing Conference (WRSC/IRSC) and Microtransat have sparked an explosion in the number of groups working on autonomous sailing robots. Many of the challenges in building truly autonomous sailing robots still remain unsolved. These proceedings present the work of researchers on current and future challenges in autonomous sailboat development, presented at the WRSC/IRSC 2014 in Galway, Ireland, 8th – 12th September 2014.