There exists an exact dynamic analogy between a sailboat and a sailplane, if it can be assumed that the sail does not generate moment around the mast and that the moment due to heel can also be eliminated. It is shown, both theoretically and experimentally, that a directionally stable sailboat can be realized. It is also shown that the above assumption of no-sail-moment can be realized by introducing a new type of mast which can elastically rake in the pitch direction and a wing sail which can freely rotate around the mast. The effectiveness of these sail and rig is verified by experiments.

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