The Caribbean has been considered as a potential region for the winter production of processing cucumbers (Cucumissativus L.). The industrial framework, transportation considerations, production costs, and marketing strategies are evaluated by utilizing pertinent studies, trade journals, and industry interviews. Three marketing strategies will be discussed; brined, fresh green stock, and attracting the processor to the region. Of these, producing fresh green stock has the greatest short term potential. This can be achieved through securing grower contracts and competitive backhaul rates, market proximity, and reduced production costs. These factors justify the Caribbean as a viable alternative to established areas for the export of cucumber products to the U.S. market during the winter season. The development of this market can be enhanced by improvements in the Caribbean transportation networks and stable governments.