This study measures the communication ability of wineries in two extreme territories of Southern Italy, Mount Etna and the island of Pantelleria. The evaluation of four dimensions of web communication was carried out by the AGIL Scheme (i.e. adaptation, goal-attainment, integration, latent pattern maintenance). The study provides a generalizable model to be applied in other similar studies. Also, focus groups of experts were carried out. The method proved to be suitable to measure the communication effectiveness of wineries through websites. Extreme territories may add value to the wine, regardless of the brand. The heroic wines may become the symbol of these territories helping environmental safeguard and contrasting territory abandonment by rural communities. The findings highlight that effective communication of heroic viticulture may be used to reposition these wines and increase their competitive advantage in foreign markets. The study generates new ideas for reflection on new types of web communication.