This article presents an exploratory study aimed at analyzing the instructional design of learning personalization practices in three secondary education centers that promote connections between students' learning and/or their learning experiences in and out of school. We propose three dimensions for analysis, according to a constructivist and sociocultural perspective: the learning activities and contents designed to connect students' learning and/or learning experiences across different contexts; the educational agents that enhance these connections; and the mediating tools used. Results indicate that our multidimensional model is useful for identifying the different didactic strategies that appear in each case to foster connections, and for detecting the aspects that need improvement. Conclusions suggest that in personalized learning environments, the focus of educational activity must be shifted from making connections between students' learning to the learning experiences that students have at different times and in different contexts, helping them to build their personal learning pathways.