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Many pleasure trips are often characterized by the visit of more than a single destination. Despite the topic is well documented in literature, the empirical studies are limited to a few pioneering studies. This lack may be attributable to the failure of tourism organizations to collect data on multi-destination trip behaviors, as it results, for example, from the system of European statistics on tourism (according to the Council Directive 95/57 EC), where no information on the average number of destinations visited within a single trip are provided. This paper aims to analyze the main implications of multi-destination trips both on tourism statistics and in tourism planning, and to describe the research design and the solutions adopted for the analysis of incoming tourism in Sicily. Some results related to the number of destinations visited and on the main travel itineraries undertaken by tourists in Sicily derived from the survey are presented.