Educational outcomes in Portugal vary across regions, reflecting territorial and socioeconomic disparities. This paper examines how geographic location, regional socioeconomic conditions and school factors are associated with student achievement, using published evidence from PISA and TIMSS, Portuguese empirical studies, regional indicators and policy documents. The analysis combines a targeted narrative review, descriptive analysis of published international-assessment estimates and an exploratory comparative institutional analysis of Madeira and the Azores. PISA 2022 reported that Portugal scored 472 in mathematics, 477 in reading and 484 in science; Madeira recorded 474, 487 and 492, respectively, whereas the Azores recorded 408, 413 and 417. Previous Portuguese research indicates that socioeconomic composition and observable school characteristics account for an important share of regional differences. The Madeira–Azores comparison is interpreted as an exploratory institutional comparison, not as a causal or quasi-experimental test. The study does not estimate the effects of teacher-policy arrangements on student achievement; rather, it identifies hypotheses about how teacher education, professional learning, institutional capacity and wider territorial conditions may interact with regional inequalities. These findings support future research and policy development on context-sensitive approaches to educational equity in geographically peripheral regions.