He says sailboat when him and Jack meet at the stadium before Jack operates on his future wife. He tells Jack he is training. But why do we even think that he may have been telling the truth. I don't think Desmond was training for nothing at all except to see how Jack would perform with a little manipulation, and Jack did well, he performed a miracle. I think if we look into all the peoples flashbacks they are coersed (I think that is how you spell it) by someone into doing something they don't want to or they don't think is possible. Hense the human experiment on behavioral patterns.