In the new economy SMEs face new challenges in their B2C transactions, such as the use of new Information and Communication Technologies (ICT). Electronic commerce may represent a com-petitive advantage to make enterprises more visible to consumers. The main barrier to the development of successful e-commerce business is represented by websites not meeting basic accessibility and usability features. To tackle this issue, heuristic evaluation and the gap analysis approach has been adopted. Website usability issues have been measured by a panel of consumers assessing a selected website each. Potential e-consumers simulated an online purchase, thereby allowing them to acquire insights on the importance and prospective satisfaction on each of the usability issues taken into considera-tion. The statistically significant usability issues mainly involve efficiency of navigations (useful naviga-tion tools or sequence of navigation), accuracy in content and supplied information. Additional in-formation underlining the link between wine production and its territory enhances consumers? iden-tification. Consumers are more keen to purchase by easy structure of websites than design and style.