A "hitchhiker" pest is defined as an agricultural pest organism moving in or on a commodity which is not one of its hosts or moving in or on a conveyance (airplane, ship) or shipping container. Our objective was to examine the movement of plant pests as hitchhikers in trade. We examined USDA data and the scientific literature to address the frequency of hitchhiking pests arriving at airports and maritime ports in the Greater Caribbean Region. We concluded that most insects, mollusks, weed seeds, and plant pathogens are likely to survive shipping conditions. Of the 6.2 million cargo containers entering maritime ports within the Greater Caribbean Region, more than 1.4 million were estimated to have arrived with contaminants. The immense number of conveyances and containers circulated in international trade make this a pathway that presents a high risk, but is difficult to control.