In 2011 during a study tour of Sobata (Shivta), a debate took place concerning the likelihood that the central Negev settlements of Elusa, Sobata, Oboda, Ruheiba and Nessana (fig. 1) were significant partners in the trade of prestige Gaza wines during the 5th and 6th c. A.D. I challenged the participants as to whether these sites’ production facilities were of sufficient magnitude to produce a wine surplus for shipping across the Roman world and whether the transport of a bulk product in relatively heavy amphoras to the seaports at Gaza and Ashqelon c.100-120 km distant was both physically feasible and economically viable in the absence of paved roads. This paper will analyse a series of factors, including demography, agricultural technology, wine production capacity and transport possibilities to evaluate the region’s potential and the likelihood of these settlements playing a part in the wine trade of Gaza and Ashqelon.