Culture-oriented tourists are a new, emerging, category of travelers. They live a vacation as a learning experience - an opportunity to discover unexploited resources of an area, including folk traditions, habits of the everyday life, rituals, history, or gastronomy. They look for original, engaging and customized traveling proposal. The MEDINA project (partially funded by the European commission) aims at developing a transnational web portal to promote culture- oriented tourism in the Mediterranean basin. The portal addresses multiple aspects of cultural heritage, highlighting the local identify of the fourteen Mediterranean countries involved in the project and pinpointing the trans- Mediterranean dimension of their civilizations, their commonalities, and their cross influences. MEDINA will also develop the organizational and technological infrastructure for the sustainability of the portal, after experimental phase. The paper discusses some of the key MEDINA issues