During the last years, economies and societies have seen a continuous change inside all their aspects. In this scenario, tourism has always played an increasing crucial role in the growth of many countries and the adoption of Information Communication Technologies (ICTs) has led to several transformations in the core of this sector. Specifically, tourism has registered a tremendous growth in the diffusion of technologies which tourists interact with for searching information, communicating, generating content, transaction, and has seen the use of tools like mobile apps, social media platforms, virtual tourism communities, able to transform the tourist’s travel experiences and to support tourists in discovering new attractive destinations, scheduling activities, personalizing their travel, and, more in general, making smart decisions. Moreover, the use of ICTs has culminated with the notion of Smart Tourism Destinations (STDs), where ICT is a driver for a smart growth and for the competitiveness of a destination. Further studies have enlarged this idea, highlighting that the fundamental constructs of a STD are human capital and social capital constructs, supported and enabled by advanced ICT infrastructures. In order to work toward the development of a smart and sustainable tourism destination, it is necessary to assess the “state of the art” of a tourism destination under different perspectives and evaluate its promptness to adopt a smart configuration. In literature several authors have considered many aspects of smart tourism and STD. Nevertheless, there is the need of investigative and holistic frameworks able to integrate all the perspectives of a STD. Accordingly, the aim of this paper is setting up a conceptual methodological framework that integrates different levels of analysis using several dimensions characterizing a tourism destination. Such framework attempts to assess and evaluate the state of the art of a tourism destination in terms of smartness, to provide hints among the tourist actors toward the development of a sustainable tourism destination and to improve the customer perception of a destination.