Spatial orientation is the ability to maintain knowledge of our position with respect to other cues within an environment. This is an essential skill, forming the foundation of other abilities, including spatial navigation. Previous research has identified that virtual environments impede participants’ ability to orient accurately. Research exploring the role of environment type, specifically nested environments, has further identified a situation which hinders orientation ability. This thesis seeks to link these research bodies, exploring orientation ability within virtual nested environments. Across a series of experiments, it was found that participants struggled to accurately orient within these environments, especially when a link to the external environment was unavailable. The addition of orienting cues within the environment, however, reduced this difficulty. Participants provided with additional cues recorded significantly lower orientation error. This effect is apparent following either active exploration or a passive video tour. Subsequent studies illustrated that other factors such as anxiety, as manipulated via the use of stereotype threat, also influenced orientation accuracy within a nested environment. Geovisualisations were explored to examine whether orientation difficulties are observed in symbolised, rather than realistic, virtual environments. Participants reported orientation difficulties and demonstrated an inability to accurately track their position within symbolised space. Results suggest that geovisualisation users, similar to users of virtual nested environments, require increased support to efficiently orient. Results support that orientation within digital nested environments is difficult due to the lack of consistent visual cues within the multiple aspects of the environment.