The current study aims to shed light at factors that contribute to tourists’ satisfaction and specifically we are interested in the contribution of ICTs in tourists’ satisfaction and in consequent destination loyalty. The study took place at a Greek island. 139 tourists participated at the study. Cluster analysis revealed three groups of tourists: the first group consists of tourists who are “satisfied-independent” the second group are the “satisfied-organized” and in the last one are tourists who are “not satisfied”. The three groups differ in their satisfaction level and propensity to revisit the destination and recommend it to others. Quantitative data were analyzed in structural equation modelling (SEM). The results support the hypotheses: 1. Tourists’ preferences on travelling organized or independent affect their destination loyalty 2. Tourists’ booking preferences affect their satisfaction 3. Destination image positively influence Attribute satisfaction 4. Destination image positively influence Overall satisfaction and 5. Overall satisfaction positively influences Destination loyalty. These findings offer important implications to destination marketers and to local authorities in designing successful marketing strategies.