The purpose of this study was to investigate the lesson planning practices of three experienced band teachers at the high school level. For the purposes of this study, experienced teachers were those with 25 or more years of teaching experience. Research questions were: (a) how do experienced high school band teachers plan for teaching, and (b) how do they draw meaning from the lesson planning process? The study employed a comparative case study design to provide rich, detailed description of both planning processes and the meaning attached. Data sources consisted of lesson planning artifacts, a focus group interview, and individual interviews. Findings suggested that participants' planning was multi-layered, nested, linked to reflection, and flexible. Participants regarded lesson planning as important but rejected prescribed lesson plan formats. Recommendations for future research and implications for practice are discussed.