Supervision is at the core of every successful organization or institution. The fundamental thrust of this study is to examine the challenges external supervisors encounter and the mitigating measures they employ to ensure supervision of schools in island communities within the Krachi-East and Krachi-West Education Directorates in the Oti Region, Ghana. The study employed the mixed method approach to studying phenomena, precisely the sequential explanatory mixed method. The quantitative data was gathered from seventeen (17) participants and analysed descriptively using mean and standard deviation with the help of the SPSS software package and presented in tables. The qualitative data from three (3) interviewees was analysed based on themes that are related to the research questions. The study established that the accessibility of island schools by external supervisors was a major challenge. This was due to a lack of readily available canoes and the required accessories for safe travelling by water. The study recommends that schools in such enclaves be provided with outboard motors, canoes, and life jackets as well as operators.