This paper uses two complementary examples from an autoethnographic study of learning and sailing to explore some connections between informal lifelong learning activities, their objects (purposes) and the hybrid (digital and material) technologies on which they depend. The examples focus on an aspect of the craft of sailing and on understanding the relations between sailing, place and local history. The paper argues that close attention to activities in which people engage can help discover some less visible purposes of learning and can broaden our understandings of situated skills. The paper also argues that being able to find and configure environments suitable for learning are important capabilities for successful lifelong learners. The paper has two additional implications for thinking about research and development in educational technology. First, a technology becomes educational by virtue of its relation to emerging activity, rather than because of any intrinsic physical properties. Second, educational technologies are often assembled in complex meshworks. Understanding how they function involves analysing dynamic relations and interdependencies: listing the affordances of individual components is not enough.