To acquire the wind energy of the oceans, a sailing wind farm has been proposed. The wind farm considered is composed of a semisubmersible floating structure, 11 windmills, four sails, six thrusters, and storage for hydrogen. To maximize the acquired energy, an effective algorithm to search for optimum routes was developed. The algorithm is based on the fact that beam winds yield a maximum of acquired energy. This feature reduces the computation time, and, consequently, efficient route optimization becomes possible in a reasonable time. After setting an operational area for the wind farm, navigation simulations for a 1-year period were carried out. A numerical weather forecast was used as well as the responses of the floating structure, such as the speed of the structure, the output power of the windmills, and the time of course changes. In the simulation, the wind farm evades rough seas to avoid structural damage, and an optimum route is searched for. The capacity factor of the system was used to evaluate the efficiency of the optimized routes. From the simulations, the maximum capacity factor achieved was 42.6%. The dependency of the capacity factor on the initial position of the wind farm was also examined. It was shown that offshore from Sanriku in northeastern Japan is an area suited to the operation of the wind farm. The effect of the initial position on consecutive periods of operation is discussed.