A hazard assessment has been performed on rock slopes impending over a segment of the Taorminese Road, which connects two popular tourist destinations in northeastern Sicily: the urban centers of Taormina and Castelmola. The road crosses steep rock slopes with a complex geological and tectonic history. The section of the road close to Castelmola is often affected by rockfall phenomena, causing injury to people and serious damage to buildings and traffic. The study analyzes the geostructural setting of the unstable rock masses, by evaluating their mechanical properties and the kinematics of potential failures. Rockfall simulations confirm that falling rocks would involve the Taorminese Road with different kinetic energy rates and prove useful for suggesting the most suitable mitigation technologies for future remedial works. The modified Rockfall Hazard Rating System has been applied to highlight the different levels of hazard along the road. The compiled hazard map shows that portions of the slopes need urgent remedial works, especially because Taorminese is the only access road to Castelmola and its interruption would lead to the isolation of the village.