Recreation Centers and Programmes have historically been designed by adults for adolescents as places of refuge, rehabilitation, and recreation. However, today’s virtual play spaces, such as Teen Second Life, differ in that the play environment is co-constructed by children. Yet, similar to traditionally adult constructed play spaces, an adult presence within Second Life protects young users from adult and sexual content. This duality creates a unique virtual space in which the benefits of both free and constructed play are present. In addition, the offline anonymity of virtual interactions offers another level of safety and freedom that promotes identity exploration and experimentation. This paper will discuss the relation and interaction between virtual space and the creation of technologized cultural tools, the similarities and differences of virtual and physical play, the value and benefits of virtual play, as well as the possible detriments of children’s play becoming exclusively confined to virtual space.