The present contribution discusses some methodological choices undertaken by a team of researchers and educators in order to encourage the school inclusion of young children in six Roma communities located in the region of Thessaly (central Greece). For several reasons, well documented in our previous research papers, Roma children face serious conflicts when they are required to participate in formal school practices (e.g. oral linguistic code, bilingualism, cultural diversity, language marginalization, boundary identities). At the same time, a ‘top-down’ curriculum policy serves mainly to perpetuate marginalized and inferior positions in terms of both learning and cultural identities and is highly connected to Roma children’s low motives for participation and high dropout rates. Taking the above into account, we have explored the possibility of a sociocultural and political posture towards designing and implementing learning activities (in the form of local based curriculum and playful outdoor activity) addressing issues of language and mathematics that are purposefully rooted into local authentic practices. For this purpose a systematic fieldwork went hand in hand with activity design that aimed to incorporate familiar artefacts to bridge discursive practices amongst communities and to develop dialogical spaces for Roma, and non-Roma, children to renegotiate their learning identities.