In the context of power system decarbonization, the demand-side strategy for increasing the share of renewable energy is studied for two constrained energy systems. This strategy, which is currently widely suggested in policies on the energy transition, would impact consumer behavior. Despite the importance of studying the latter, the focus here is on decisions regarding the type, location, and timeframe of implementing the related measures. As such, solutions must be assessed in terms of cost and feasibility, technological learning, and by considering geographical and environmental constraints. Based on techno-economic optimization, in this paper we analyze the evolution of the power system and elaborate plausible long-term trajectories in the energy systems of two European islands. The case studies, Procida in Italy and Hinnøya in Norway, are both electrically connected to the mainland by submarine cables and present issues in their power systems, which are here understood as relatively isolated power systems. Renewable energy integration is encouraged by legislative measures in Italy. Although not modeled here, they serve as a backbone for the assumptions of increasing these investments. For Procida, rooftop photovoltaics (PV) coupled with energy storage are integrated in the residential, public, and tertiary sectors. A price-based strategy is also applied reflecting the Italian electricity tariff structure. At a certain price difference between peak and off-peak, the electricity supply mix changes, favoring storage technologies and hence decreasing imports by up to 10% during peak times in the year 2050. In Norway, renewable energy resources are abundant. The analysis for Hinnøya showcases possible cross-sectoral flexibilities through electrification, leading to decarbonization. By fine-tuning electric vehicle charging tactics and leveraging Norway’s electricity pricing model, excess electricity demand peaks can be averted. The conclusions of this double-prospective study provide a comparative analysis that presents the lessons learnt and makes replicability recommendations for other territories.