The relationship between the representation of landscapes and the production of landscapes are integral. Drawings, models, or other types of representational tools offer possibilities in understanding the landscape in different ways and are a critical part of the design process rather than simply a presentation tool. In this studio, we shifted between drawings and models, experimenting with an iterative and cyclical process of documentation and speculation. Students used established means of representation to develop a composite and complex understanding of the landscape. The studio examined the relationships between people and the natural and built environment. Through a series of exercises, students developed their skills in landscape architectural representation; identified and analyzed key aspects that shape a site context; developed a vocabulary to build landscape experiences and proposed appropriate interventions in natural and developed contexts. The final design exercise was sited on the Jubilee Battery, an area rich in history and subtropical ecology in Hong Kong Island. Remnants of Hong Kong’s coastal defense batteries are juxtaposed with a newly constructed educational facility, bringing a diverse set of users to the site. Students explored a dynamic palimpsest of the site which led them to the design of a path and a sequence of outdoor spaces.