I aim to advance the study of the Roman economy by exploring economic connections in the rural landscapes of southern Italy from the second to sixth centuries CE. Historical approaches to the Roman economy focus on the big-picture processes of a Mediterranean-wide system, while archaeological approaches focus on the small scale. I bridge them by investigating how the interaction among local, regional, and pan-Mediterranean economies influenced and contributed to overall processes. Engaging critically with Horden and Purcell’s paradigm of connectivity, I develop an archaeological methodology to understand how people, places, and economies were connected in the past. Southern Italy was unique for this period, experiencing seeming prosperity when much of the Italian peninsula was in decline. From the perspective of three Roman provinces—Lucania, Apulia, and Campania—I study how the links between different scales of economic activity contributed to the unique circumstances of this region.