The main objective of this chapter is to understand if Destination Management Organizations (DMOs) are effectively exploiting the potential of the digital world and are considering online information in the management model of tourism destinations. To this end, an exploratory study was carried out, focusing on a regional DMO in Portugal: Tourism of Alentejo/Ribatejo. The methodology used in this study unfolds in three phases: (1) a content analysis of strategic and operational plans and/or activities of the DMO under study; (2) analysis of its online presence, namely its website, social networks, and positioning in the Google search engine; and, finally, (3) a semi-structured interview with the president of the DMO. The results indicate that DMOs start to wage digital communication, opting to be on the Internet through their own website and with a profile created in some social networks. However, their activity in social networks is not regular. On the other hand, DMOs are still in a very incipient phase in the use of web and social networks data to support the organization's decision making.