Sail Freight has slowly worked its way into the realm of sustainability discourse as a way of reducing emissions from transportation, providing logistical solutions using the emissions free power of the wind and technologies proven effective for over 5000 years. This attitude toward Sail Freight and transportation in general has some merits, but none of these discussions seem to have examined the issue of readopting sail freight at scale. This paper proposes methods of understanding this issue of scale by calculating the needs of a city for food. Using foodshed analysis to calculate necessary fleet capacities therefrom, as well as the labor needed to support this fleet, a model is provided for the New York Metro Area. The capacity for building this fleet and training sailors with current sail freight infrastructure and operations is then examined, with recommendations and analysis for addressing these challenges over the coming decades.