Nowadays, following the increased interest and need for the issue of sustainability, tourist destinations are called upon to promote sustainable tourism development through the implementation of investments and initiatives. Despite the investments by the destinations, how are these perceived by tourists and residents? Based on this, this paper aims to assess the perception of sustainable investments in a coastal area located in Tuscany, through the administration of a questionnaire among 750 people, including both tourists and house owners. The study adopted statistical logit and probit models to detect the perception of sustainable initiatives in relation to beach satisfaction. Moreover, this research developed a model for understanding if there are substantial differences in perception between Italian and foreign beach users and at the same time between residents/house owners and tourists. The findings reveal that those who perceive investments in sustainability are more than satisfied with beach and facilities. The model shows that foreigners and residents/house owners perceive sustainable investments implemented in the destination more than tourists and Italian respondents. This research can provide support to local operators and policymakers in defining the destination image in relation to sustainability.