This autoethnography explored my experiences in designing a nature-based literacy unit in Hawai'i. Whereas a small body of research highlights a positive relationship between nature-based experiences and literacy outcomes, there is minimal research on the planning process. I wanted to understand the experience of planning for nature-based literacy learning events. Using Rosenblatt's transactional theory, this study explored how outdoor spaces can promote literacy learning. Data collection included lesson plans, unit plans, researcher journals, and artifacts. Data analysis and interpretation was conducted using familiarizing, coding, grouping, and writing. The findings indicate that the local environment can be read as an environmental text while simultaneously serving as a context for traditional print text reading and writing. Four themes emerged from the data: the environment as text, cultural significance at the center of the unit, challenging nature of logistics, anxiety, and unpredictability, and motivation and engagement are central aspects of planning. The research demonstrated that educators must determine what constitutes 'nature,' question the boundaries of efferent versus aesthetic reading, and should recognize how their prior experiences influence their lesson and unit planning. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]