As students of Islam, we internalize the idea of the pre-modern Islamic world being a well-connected commonwealth. Generations of scholars have fortified this idea through their close reading of primary sources. However, the latest digital studies in other disciplines (primarily, literary history) show that many academic ideas that became practically axiomatic are based on unsystematic treatment of primary sources and may well be distorted. The paper thus seeks to re-evaluate the notion of the "connectedness" of Islamdom through digital analysis of biographical collections. Biographies often mention places which their subjects visited. Such itineraries provide us with an opportunity to represent each individual on a geographical map as a series of connected dots. Using text-mining techniques and geographical information systems (GIS), one can combine thousands of such itineraries into a map showing connections between Islamic urban centers and province. More importantly, a chronological series of such maps will allow us to look into how these connections changed over time. The paper will discuss major methodological challenges and possible ways of modeling "connectedness" based on data available in biographical collections. The paper will offer a preliminary analysis of al-Dhahabi's "History of Islam" and major biographical collections of legal schools.