Maritime security is an issue of vital importance in International Maritime Law. From a human rights and humanitarian perspective, the human element of maritime security is worthy of specific focus, particularly in light of the present world economic crisis. This crisis has highlighted the threats of human trafficking and maritime migrant smuggling, both of which are long-standing issues. These issues are prevalent in many areas of the globe. The Caribbean has for decades had a particularly acute problem in these areas. However, from a maritime perspective, maritime migrant smuggling is more topical in light of the sea transportation element. A combination of desperation and dissatisfaction has for years influenced numerous persons to flee north by boat, thereby endangering, and in many instances losing, their lives. This work explores the motivations behind and the methods employed in such travel within the region, the major places of origin and destination, and the International Conventional response to the problems. Ulitmately, it focuses on Jamaica and suggests legislative and other measures to tackle the problem of Haitians arriving in Jamaica illegally by boat.