AbstractWith the adoption of the United Nations’ Agenda 2030, some member states of the European Union have voluntarily assessed their state regarding the 17 Sustainable Development Goals (SDGs) by use of the United Nations’ monitoring system for administrative bodies. However, this system does not consider specific challenges in achieving SDGs that are faced with respect to vulnerable geographical contexts. Among these contexts falls the emblematic case of insular regions suffering from particular natural and geographical “handicaps” that, in most cases, confine their efforts to SDG achievements. The goal of this paper is to feature a monitoring system that is capable of measuring progress of insular territorial contexts to 2030 SDGs; the study is adjusted to the islands’ particularities. In doing so, the link between the structural problems of the islands and the UN 2030 SDGs is established, feeding the design of a monitoring mechanism by means of an Islands Sustainable Development Index (IISD). IISD integrates environmental, social, economic, and innovation dimensions, represented by four core indicators, namely the IEND, ISD, IED, and IID, respectively. The results of this research demonstrate: (i) the need to assess progress of the islands toward the SDGs, taking into account the “insularity” dimension, that is, incorporating in the monitoring system respective intrinsic and extrinsic peculiarities of such territorial contexts; and (ii) how intrinsic quantitative and qualitative attributes of island regions, embedded in an integrated analytical approach, can inform strategic decision making in order to achieve higher levels of sustainability performance in these specific territorial entities.