The article revisits how Zionist sport activists and leaders in the Palestine of the 1920s and 1930s portrayed the desired transformation of their bodies and identities. It focuses, in particular, on the role that images of the “orient” played in that wishful transformation. For this purpose, the paper juxtaposes two different sport experiences that were carried out by members of the Maccabi Sport Organization: hiking expeditions within Palestine of the 1920s and 1930s and two motorcycle tours from Palestine to Europe, held in 1930 and 1931. In focusing on these two divergent examples, the article shows how the wishful transformation that Zionist sport activists and leaders expressed was informed by what could be termed re-orient-ation. By using such a term, the article points to an unresolved desire to actively re-build a local Palestinian Jewish identity while simultaneously preserving an obdurate self-image of a European settler in a degenerate East.