All children and young people need to play. The impulse to play is innate. Yet, the pure essence of play is playfulness a notion not new, yet limitedly researched. Playfulness refers to the individual style each child has to play, which is linked to personality descriptors and attributes. The present study had a twofold aim. On the one hand, it aimed at assessing Greek preschool children's playfulness employing Children's Playfulness Scale. On the other hand, it aimed at examining whether personal and family variables affect children's playfulness. Results suggest that the sample exhibits rather medium levels of playfulness and that during play they enact more cognitive spontaneity, compared with other components of playfulness. Thus, correlation analysis showed that playfulness components predict one another and that several personal and family characteristics correlate with playfulness' aspects. Implications are discussed and suggestions for future research are formulated.