The cultural components of drawing allow one to consider it a symbolic form of cultural communication. The behavioural and cognitive mechanisms involved in the cultural transmission of symbolic communications are situated in an environment embedded in cultural-historical features that should be taken into account, as they give rise to variations in socio-cultural practices. The aim of the present paper is to provide evidence of a range of different pathways through which the acquisition of drawing emerges in divergent cultural contexts. This work stems from the international Day in the Life (DITL) project. From the DITL dataset countries, we show how family members in seven (in Thailand, Peru, Italy, Canada, the UK, the USA, and Turkey) expose their 30-month-old child to opportunities for experiencing drawing. We focus on the way the children are given the opportunity to draw, their spontaneous uptake, and on the different modalities through which they discover relationships between drawings and the objects they represent. In the different interactions observed, we confirm the omnipresence of situations that child development research has identified as promising for drawing-skill development. In all contexts, drawing materials, shared child-adult attention, dyadic asymmetrical relationships, and reciprocal involvements are found to be present.