8. San Juan, Puerto Rico
Despite being an unincorporated territory of the United States, many consider Puerto Rico to be a Caribbean island as well. Relatedly, this island finds its way on this list due to an enduring struggle with crime and political corruption.
A cycle of violence has been identified through an increase in organized crime, illegal drug trade and alleged governmental involvement in such violations. Indeed, the island is not as safe as it used to be–especially in the city of San Juan. A wave of daytime violence linked to drug trade has kept tourists reluctant to visit the island altogether.