This chapter begins with a brief description of the Caribbean Islands and the area's historical relevance. The drastic change in Caribbean settlers' lives are also discussed in the succeeding parts. As the chapter progresses, a series of security problems surrounding the region are discussed. The sudden increase in the number of criminal cases in particular republics in the Caribbean region are examined. The growing crime rate in the area as well as the effects of more complex criminal modus operandi are also tackled. The problems that the region faces regarding much serious crimes such as the rampancy of drug trafficking and abuse as well as indiscriminate bloodshed are scrutinized. This chapter also gives a breakdown of the effects of the increasing crime rate in the Caribbean region. Also included in the chapter are security measures that the authorities have been resorting to in order to bring peace and order to certain parts of the region. However, in places the chapter provides arguments regarding the securitization of the region and how much will it affect the republics therein.