Natural phenomena triggered by different sources generate natural hazard events, such as extreme weather events, earthquakes, volcanic eruptions, fires, landslides. These phenomena often lead to serious consequences such as damage to the natural territory, structures, and infrastructures, and loss of human lives. Generally, risk is the probability of damage due to the hazard of the events and its interaction with exposure and vulnerability of the affected humans and environments. Therefore, understanding the processes that trigger natural phenomena, and their modeling, are key factors in the assessment, planning, and management phases of these risks and the choice and design phases of adequate and sustainable mitigation measures. From this point of view, Calabria, a region in Southern Italy, represents an interesting case study due to its geomorphological, climatic, hydrological, and anthropic peculiarities which make it extremely susceptible to natural disasters as it happened several times in the past with earthquakes, tsunamis, floods, fires. Therefore, the paper, through the case study of Calabria, describes a multilevel analysis of natural hazard events. The main objectives concern understanding the mechanisms that generate natural hazards in complex territories particularly subject to phenomena such as the Calabrian one and understanding the mechanisms that create compound or sequential phenomena, also considering the presence of amplification factors such as anthropization and coastal erosion. This analysis is divided into six levels. Level 0 involves the cognitive analysis of natural hazard events typical of the Calabrian territory. Level 1 consists of the analysis of the most important natural hazard events that occurred in Calabria. Level 2 involves the definition of hypothetical event scenarios; for example, the occurrence of an important past tsunami or flood considering the territory’s current anthropization. Level 3 involves a rapid analysis of the effects produced by these scenarios. Level 4 involves a detailed analysis of the effects produced by these scenarios. Finally, level 5 involves the analysis of the triggering mechanisms of the natural hazard events, the probabilities of compound or sequential natural hazard events, and the amplification factors. These analyses are crucial for effectively planning and managing territories subjected to natural disasters and identifying possible mitigation measures.