Sleep disturbances are more common in patients with Parkinson's disease (PD) than in the general population and are considered one of the most troublesome symptoms by these patients. Insomnia represents one of the most common sleep disturbances in PD, and it correlates significantly with poor quality of life. There are several known causes of insomnia in the general population, but the complex manifestations that might be associated with PD may also induce insomnia and impact the quality of sleep. The treatment of insomnia and the strategies needed to improve sleep quality may therefore represent a challenge for the neurologist. A personalized approach to the PD patient with insomnia may help the clinician to identify the factors and comorbidities that should also be considered in order to establish a better individualized therapeutic plan. This review will focus on the main characteristics and correlations of insomnia, the most common risk factors, and the main subjective and objective methods indicated for the assessment of insomnia and sleep quality in order to offer a concise guide containing the main steps needed to approach the PD patient with chronic insomnia in a personalized manner.