Many island municipalities depend upon the tourist industry, but this industry can be a double-edged sword. On the one hand, it provides a source of income to people in the region, using the natural resources they have. On the other hand, the low-skill services that are connected to tourism have low wages and productivity, and the possibilities of productivity increases are low. This article aimed to analyse the possibilities for economic development in the Croatian islands, using a conceptual model inspired by Harris and Todaro’s theoretical outline (Harris & Todaro, 1970; Todaro, 1969). We analysed 18 municipalities located on the islands. The conceptual model classified municipalities by three criteria: unemployment rate, employment growth, and wage. We found 18 island municipalities that have low unemployment, high employment growth, but still low wages, which is a contradiction in neo-classical economic theory. However, it can be explained by the existence of amenities and the tourist industry being low-skilled and therefore having a low wage level. We used population data to analyse demographic trends and the propensity to move from these municipalities. Regardless of the high quality of life on islands, employment possibilities are very limited, particularly for persons with tertiary educational attainment. Therefore, in the past, people born on islands have had to seek education and employment on the mainland. However, telework and digital nomadism have dramatically changed the situation. With digitalisation and flexible work, there are new possibilities for the islands to attract people to both work and spend leisure time. This has led to a number of issues, not least the question of taxation.