Previous studies show that the quality of the tourist experience is affected by a large set of factors, many of which not directly related to the acquisition of specific products or services. Research also shows that tourist satisfaction is a determinant of destination loyalty. This study explores this topic by empirically analysing how the relationship between the satisfaction with the tourist experience and destination loyalty is affected by personal factors, such as socio-demographic characteristics and travelling motivations. This study is based on a small region representing an important destination in Algarve, Portugal, and uses data from a survey conducted on tourists of different nationalities during peak season. We identify the reasons leading to dissatisfaction with the tourism experience and, based on structural equation modelling, ascertain the relationship between satisfaction levels with the tourism experience and tourist destination loyalty. Then, a multiple group analysis provides a detailed overview of this relationship by establishing in which groups of tourists the relatedness between satisfaction and destination loyalty is stronger or weaker. In this sense, this study provides an important backdrop for destination managers looking to offer more effective and targeted marketing strategies.