In this chapter, the authors trace three key concepts — climate, landscape and feeling — as they are manifest in different parts of Western Europe between the medieval and early modern period and across a number of discursive genres and styles. They discuss historical changes in the concepts of ‘climate’ and ‘landscape’ as ways of categorizing and describing human interactions with the world and its weather. The authors consider the way pilgrims, travellers and explorers move through different terrains, whether real or imagined, discovering new and comparative perspectives. They examine their methodological approach: focusing attention on the language of affect that underpins discourse about the environment that is ostensibly more ‘scientific’. Seasonal wind patterns were crucial for the pilgrimage schedule as spring ushered in north-east winds for travels across the Mediterranean to Jerusalem. The authors conclude with a longer exemplum that both signal a significant shift in the way weather and wind were viewed toward the end of period.