The aim of this article is to analyze the social media effects on enotourism. Two territories of similar extension and with historical coincidences in their development have been selected: the Okanagan Valley, Canada, and the region of Somontano, Spain. Methodologically, an analysis of the content on Twitter has been performed, collecting 1377 tweets. The conclusion is that wineries create sentimental and experiential links with the users, avoiding commercial communications. Specifically, Okanagan wineries establish a relevant conversation network on Twitter based on the high percentage of responses, which is 31.3%, but this is not so in the case of Somontano, which is 12.8%. The tourist attractions most used to create a bond are the wine landscape and the gastronomy in the case of both territories. The tourism sustainability variable remains a minor matter in the emission of messages on Twitter.