Objectives: The aim of this study was to compare a sample of Italian (n = 29) and Finnish children (n = 32) with Down syndrome for possible differences emerging from diverse educational surroundings. Besides the level of adaptive and challenging behaviors, some other issues were compared, including teacher satisfaction. Methods: We used the children's teachers as informants. They were interviewed using standardized scales. Results: No differences in adaptive behavior or challenging behavior were observed between the samples. All children from the Italian sample were fully included in mainstream classes, while in the Finnish sample, 92% of all the school years were spent in self-contained special education classes. The Italian sample received physiotherapy and speech therapy more often than the Finnish sample. Satisfaction concerning the resources and organization of the children's education was high among the Finnish informants, but rather low among the Italian informants. Conclusion: The results illustrated some differences in the organization of special education of children with Down syndrome in Finland and Italy. The interpretation of the level of adaptive and challenging behavior scores was hampered by the high standard deviations, indicating the inner heterogeneity of the samples.