This study addresses transportation accessibility challenges on Port Island, amid concerns over declining population and urban density. The aim is to gain foundational insights for improving local mobility while considering sustainability and environmentally friendly transport options. A questionnaire survey was conducted to evaluate current conditions regarding accessibility, safety, and comfort within the island’s transportation systems. Findings indicate that perceptions of accessibility differ by user group, and overall, both safety and comfort levels are deteriorating. The study highlights that rather than expanding conventional public transportation, a more tailored approach is needed—one that enables individuals to travel at the right time and place, based on personal needs. These results suggest the introduction of flexible, demand-responsive personal mobility solutions may offer a more effective and sustainable transportation strategy for Port Island’s future.