This chapter proposes the theme of the history of travel and travelers for a comprehensive approach to teaching and learning history for active citizenship education. In particular, we analyze briefly on the historical ways: itineraries, routes, and cultures. From the routes of faith to the itineraries and routes of trade to the routes of conflict (European explorations and conquests in the Americas, from the crusades to the world wars) and their participants; your travel and trade. Over the millennia, the sea has been the main vector of trade and the Mediterranean ports have been crucial places for the economy. Networks of exchanges from foodstuffs to metals, from timber to grain, spices and textiles, men, women, slaves, yesterday as still today; the journeys and mirages of forced nomads. These are contents that through an active methodology can offer a critical approach to the phenomenon of travel considered decisive for the elaboration of European societies and make students acquire a vision of the complex relationships existing between different cultures through an approach by outcomes of history. Knowing the fundamental moments and processes of the European history of time travel with glances at world history starting also from personal and local history and expounding historical knowledge by making connections and arguing one’s own reflections, we believe can develop education for democratic citizenship through critical and responsible behavior inspired by the values of freedom and solidarity at all levels of organized life (local, national, European, and world).