The purpose of this study was to investigate novel methods on an unmanned sailing boat, which enables it to sail fully autonomously, navigate safely, and perform long-term missions. Two robotic sailing boats have been developed especially for this purpose. A compact software model of a sailing boat's behaviour allowed for further evaluation of routing and obstacle avoidance methods in a computer simulation. The results of real-world experiments and computer simulations are validated against each other. It has been demonstrated that autonomous boat sailing is possible by the effective combination of appropriate new and novel techniques that will allow autonomous sailing boats to create appropriate routes, to react properly on obstacles and to carry out sailing manoeuvres by controlling rudder and sails. Novel methods for weather routing, collision avoidance, and autonomous manoeuvre execution have been proposed and successfully demonstrated. The combination of these techniques in a layered hybrid subsumption architecture make robotic sailing boats a promising tool for many applications, especially in ocean observation.