Source : Webster's Revised Unabridged Dictionary (1913)

Sharpie \Sharp"ie\, n. (Naut.)
   A long, sharp, flat-bottomed boat, with one or two masts
   carrying a triangular sail. They are often called {Fair Haven
   sharpies}, after the place on the coast of Connecticut where
   they originated. [Local, U.S.]

Source : WordNet®

sharpie
     n 1: an alert and energetic person [syn: {eager beaver}, {busy
          bee}, {live wire}, {sharpy}]
     2: a person who swindles you by means of deception or fraud
        [syn: {swindler}, {chiseller}, {chiseler}, {gouger}, {scammer},
         {grifter}, {sharper}, {sharpy}]
     3: a long narrow shallow-draft boat with a flat bottom and a
        triangular sail; formerly used along the northern Atlantic
        coast of the United States