Florida is the peak zone for hurricane risk. The authors evaluate the current vulnerabilities and risks associated with the residential property insurance system in Florida and its financial capability to respond to future hurricane events. The state’s residential property insurance system is composed of private insurers and Florida’s three public risk financing entities: Citizens Property Insurance Corp. (Citizens), the Florida Hurricane Catastrophe Fund (FHCF) and the Florida Insurance Guaranty Association (FIGA). The Florida residential insurance market has been transformed since the last Category 5 hurricane—Andrew—made landfall, and the current system has not been tested with a major hurricane loss. The authors used the characteristic event (CE) methodology to analyze the impacts of 20-, 50- and 100- year hurricanes on the Florida market from both a micro and a macro perspective. Using a set of realistic assumptions, the analysis illustrates and quantifies Florida’s vulnerabilities to hurricane losses by estimating the numbers of private insurer insolvencies and resulting impacts on Florida’s public risk financing entities for each of the hurricane scenarios.