Urbanisation, environmental degradation, and lack of green spaces in dense metropolitan environments raises critical considerations for curriculum research. Urban densification has led to the prominence of high-rise architecture across city skylines and similar trends are underway in education where ‘vertical schooling’ (VS) is making its debut in Australia (Bleby 2016; Edwards 2017; The Urban Developer 2018). The issues discussed in this article relate to an impending future urban landscape of VS with limited space for direct contact and access to nature. Firstly, the prominence of VS within the national context is discussed, identifying critical questions relating to its potential impact on students’ access to, understandings of, and relationships with nature. Secondly, an overview of the benefits of nature and outdoor learning is presented and followed by an examination of curriculum links that support education for sustainability and place-based outdoor learning. Lastly, the new spatialities of VS are problematised, specifically in relation to the separation of schooling from community. The points and counterpoints highlight considerations regarding physical design and architecture on environmental and social sustainability, serving as a call for curriculum researchers to explore new ways of looking at nature in VS, and innovative approaches to making sense of the different meanings that become attached to such an idea.