Using a combination of scanning tunneling microscopy (STM) and density functional theory the hydrogen bond directionality and associated chirality of enantiopure clusters is visualized and controlled. This is demonstrated with methanol hexamers adsorbed on Au(111), which depending on their chirality, adopt two distinct molecular footprints on the surface. Controlled STM tip manipulations were used to interconvert the chirality of entire clusters and to break up metastable chain structures into hexamers.