A thorough literature review has shown that although there are many theories to explain international trade, researchers are unanimous in affirming that hotel chains' internationalisation is influenced by pull factors, related to specific characteristics of the host country (contextual and transactional environment), and by push factors, related to specific characteristics of the companies and of their home country. This chapter aims to identify which factors influence hotel chains choosing a destination to invest over another. With this purpose, a theoretical model, that included six pull factors related to the contextual environment and five factors linked to the tourism industry, was developed. This model was validated through questionnaire surveys applied to foreign investors running accommodation units in mainland Portugal. Fifty three questionnaires were considered valid, representing 64% of the universe of foreign investors in Portugal (accommodation sector).