||Is the drawing to scale? And just how accurate must you be with your digitizing? Is there any way for someone to survey some part of the feature in the drawing?
If the drawing was to scale, I would take the dimensions I could figure out from the drawing, go to a project with the correct georeferencing, match up something, like that shoreline so I could orient where the features on the drawing should go and then create those features using the editing tools available in ArcMap. If I had a little more info about what you're trying to draw, I might be able to suggest some specific tools.