During the summer of 2017, a musically and culturally diverse group of fifteen young musicians from Haifa, Israel, and fifteen from Weimar, Germany, came together for ten days in each city to form the “Caravan Orchestra,” a new ensemble that sought to reopen lost musical connections between cognate Jewish, Arabic, and European repertories. Seeking to explore an “often-overlooked historical, transnational cultural matrix” rooted in the long arc of the Ottoman empire, the Caravan project proved to be a wider voyage of discovery, in which a large group of stakeholders from two countries—ethnomusicologists, musicians, students, funders and institutions—explored what such a conversation might entail. Like many intensive musical projects, the Caravan Orchestra was a transformative experience for many of those involved, marked by the exhilaration of producing good music on a concert stage and validated by audience applause, dancing and ovations. Yet beyond aesthetic satisfaction, what kind of insights can such a project offer into the “disrupted musical histories” that it seeks to explore? In this article, I explore this question via three elements of the Caravan experience: musicianship, repertory, and identities.