“Linear” geographical objects such as rivers and infrastructure are increasingly proving to be interesting places to experiment with trans-scalar relational planning and design covering vast areas, which strive, not without difficulty, to go beyond the physical and non-physical limits of each disciplinary field. This article examines such experimentation through two case studies in Italy: the Progetto strategico della rete ecologica del Parco Fluviale Gesso Stura (“Gesso Stura Riverside Park eco-network strategic project”) between the Alps and the Po Valley in the province of Cuneo, and the creation of the Parco del torrente Sangone (“Sangone River Park”) near the Metropolitan Area of Turin.