The Wreck of the Zephyr by Chris Van Allsburg

From chapters.ca:
At the edge of a cliff lies the wreck of a small sailboat. How did it get there? "Waves carried it up in a storm," says an old sailor. But is it possible that waves could ever get that high? There is another story -- the story of a boy and his obsessive desire to be the greatest sailor, the story of a storm that carried the boy and his boat to a place where boats glide like gulls high above the water and not upon it. Chris Van Allsburg tells that story of the boy and his boat, the Zephyr, in words and haunting, full-colour pastel paintings. His sailboats sail the night sky with the stars in pictures so vivid that the reader can almost hear the wind in the sails.