This chapter follows on the heels of the participants of the first modern Jewish-cum-Zionist pilgrimage to Palestine in spring 1897. It was organized by the British Jewish society the Maccabean Club, and spearheaded by the lawyer Herbert Bentwich, who, on Zionist leader Theodor Herzl’s request, gathered a group of 21 Jews and non-Jews to explore the potential of a Jewish homeland in Palestine. From London to Palestine and back, the chapter unfolds how early explorers of Zionism made sense of Jewishness, nationhood, and territorial attachment or detachment to both Europe and Palestine. More specifically, it traces how the participants identified different distinctions along the way between Jewish and non-Jewish as well as civilized and non-civilized, and argues that these differences later would crystallize into Zionist and non-Zionist positions. The chapter elicits a new pragmatistic framework in which we can see Zionist (and non-Zionist) emergence as a reality that had to be validated through experiences, sensemaking, and boundary work.