Social media influencers are an integral element of firms’ social media marketing strategies. Despite growing academic interest, only a few articles address managing influencer marketing from a firm’s perspective. In addition, there is scant knowledge of how influencers interpret organizations’ guidelines and produce the content associated with their commercial collaborations with brands. This omission is critical as influencers are in control of the message conveyed to the social media audiences and require managing in order to avoid image incongruity between the firms’s own and influencers’ communications. Drawing on a multi-method study including semi-structured interviews with destination marketing organizations and influencers, ethnographic observation and semiotic analysis of social media content, the findings contribute to two-step flow communication theory by showing how the “second step”, the influencer, decodes and transmits the commercial messages to his/her followers in the context of destination marketing. Social reality – the destinations, milieus, places and businesses to be visited – and the campaign objectives are all entangled in the content narrative and interpreted by the influencer and her knowledge of her audience into what they could mean and become in the social media environments’ semiotic and symbolic landscapes. We argue that the interpretation and contextualization of the message occurs via two mediating layers: influencer’s creative process and the chosen technological platform’s materiality. Influencers’ own interpretation and understanding of the intangible objectives and influencers’ perception of the social media audience’s understanding of the certain intangible element are determinative in the interpretation and contextualization of marketing messages of the campaign’s commercial stakeholders.