This paper analyses the orientation towards sustainability in the online communication of Italian Regions, by evaluating – between December 2019 and January 2020 – the content of official tourism websites and assessing whether this orientation is associated with specific destination characteristics. Sustainability orientation of the websites is measured by the Green D-web Score, a checklist of 35 items of sustainability-oriented content. The destinations’ profile is considered in terms of adoption levels of sustainable regulations and practices, the intensity of tourism development, the size and the tourism maturity. The analysis returns Green D-Web Score scores between 5 and 32, out of a maximum of 35, with a median value of 19.5. Sustainability orientation of online communication is significantly and directly associated with the adoption of sustainable regulations and practices and the tourist pressure of the destination, while relationships with size and maturity are not significant.