The sharing economy, underpinned by digital platforms like Airbnb and Uber, which pair individuals’ needs and wants, from accommodation to rides, is on the ascent. These new business models, where capital and labour are provided by several dispersed individuals rather than by a single centralized entity, defy the operational structure of comparable traditional activities. In the sharing economy, in fact, the personal and the professional spheres blur, and selfish motivations mingle with altruistic aims, while transactions span the whole market-to-gift spectrum. Against this background, in which the classification of individuals and transactions is less straightforward, the article intends to assess the practical feasibility of specific EU VAT notions such as “taxable persons” and “taxable transactions”, as interpreted by the ECJ and the VAT doctrine. In addition, the research seeks to test these concepts against a framework of selected tax principles.