In this chapter, the author considers how his past and present personal relations to the sea as his Heimat have directly influenced his professional practice as a university lecturer. His connection to the sea starts with his annual family seaside holidays to Broadstairs on the Kent coast in south-east England for the first 11 years of his life. Aesthetic experience, cognitive understanding of place and his cultural history have shaped my connection with the sea. The author explores how the activity of sailing provides a means with which to connect students to maritime cultural heritage by exploring and studying the places where the land meets the sea: the towns, harbours and quays where we go sailing. The author considers the tension that exists, when teaching about the maritime pasts and cultural heritage, between a romanticised view of seafaring and seascapes and the historical, social, political issues of power, class and gender.