This study explores the notions of space underlying a famous Hebrew travel account from the twelfth century: Benjamin of Tudela's Sefer masa'ot (Book of travels). Instead of reading it as an eyewitness report documenting the human geography of the medieval world, I seek to understand the "aggregatory" character of a literary work that contains both empirical and imagined information about distant places and lands, some of which it shares with medieval Arabic and vernacular literatures. By means of this knowledge, the Sefer masa'ot reflects on almost the entire geographic trajectory of the then-known world. Highlighting how the book constructs the Mediterranean basin as an interconnected, Jewish space, I furthermore challenge the positivism that still dominates the scholarship on this book. My argument, which is partly based on GIS data, is that its "hodological" representation of geography according to routes does not necessarily reflect Benjamin's own movement in time and space but rather functions as a way of illustrating the connectivity of Jewish diasporas. In order to contextualize its narrative, I also compare Benjamin's Hebrew work to the Arabic Rihla (Journey) by Ibn Jubayr, a contemporaneous Muslim traveler from Granada, as well as other medieval sources. Arguably, both Benjamin and Ibn Jubayr use the (loosely defined) literary genre of the travel account to envision an interconnected and unified Jewish and Muslim oikumene, respectively.