The current evidence base for outdoor and nature-based education in a context of education for sustainability is limited and unrepresentative of the realities of small, urban schools, which tend to be characterised by small outdoor spaces devoid of nature. To address this research gap, we carried out two studies in Malta, as an example of a densely populated and heavily urbanised context. A survey conducted among educators in Maltese primary schools explored the occurrence and frequency of outdoor teaching and factors that influence attitudes, perceptions, and practice of outdoor teaching. A complementary study mapped built, hard and soft landscapes of all primary school footprints in Malta. The two studies converge to shed light on possible systemic or physical factors leading to a low incidence of outdoor teaching and in particular, of nature-based teaching in small, urban schools. Nonetheless, our findings show strong interest in such teaching approaches amongst study participants. Our study thus establishes a research priority to identify factors that could support outdoor teaching in such contexts.