This work aims to propose new methodologies for the quantitative characterization of insomnia. Sleep microstructure, as expressed by Cyclic Alternatic pattern (CAP) sleep, is studied and differences between normal sleepers and insomniacs are investigated. The dynamic in the structure of CAP activation events is studied by use of wavelet analysis and the content of events, i.e. EEG dynamics, is studied in terms of complexity analysis. Both in structure and content, features exhibiting statistically significant differences are proposed, opening new perspectives for the understanding and the quantitative characterization of sleep and its disorders.