Tourism may not sustainably support territories with limited natural resource stock such as islands. The volume of visitor arrivals and the industry investments can increase the pressure even beyond sustainable levels. There is an evident and unresolved tension between these two great polarities, sustainability and economic growth driven by tourism. The aim for policymakers is to find an acceptable equilibrium between these two dimensions. This paper investigates tourism evolution between 2007 and 2019 in 15 Mediterranean islands, comparing tourism pressures through statistical indicators. The analysis will compare tourism demand and supply trends in these contexts. The performances will be evaluated to identify the islands’ positioning between sustainability needs and tourism development opportunities while considering post-COVID-19 challenges.