Sleep monitoring using wearable data has shown promise for personal health, yet large language model (LLM)-based summarization and question answering remain insufficient for personalized sleep guidance. Training specialized models, however, often requires costly expert annotation. Moreover, privacy and accessibility concerns motivate lightweight, local deployment for end users. We present a two-stage framework to address these challenges. Specifically, in Stage~1, a multi-agent LLM pipeline reasons structured sleep guidance from unannotated wearable records, enabling scalable dataset construction. Stage~2 distills guidance reasoning trajectories into small language models (SLMs) through supervised fine-tuning and integrates a training-free Best-of-$N$ selection strategy to enhance inference. Experimental results demonstrate our method outperforms commercial general and medical LLMs and open-source models. Human evaluation further supports the quality of the generated guidance and the feasibility of personalized sleep guidance with SLMs.

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