With a pleasant wind sets this gentle, breezy tone that instantly tells you this is a summer romance visual novel and nothing bad could possibly happen here. Zansho Omimai Moushiagemasu is a 2008 PC VN and the vocal and soundtrack collection nails that nostalgic countryside warmth.
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Smile of a childhood friend has this soft piano melody that just radiates comfort. The melancholic sound of rain shifts the mood perfectly with slower, more wistful textures underneath. Even now, in my heart hits harder as a full chorus arrangement than you'd expect from a smaller title.
They even included karaoke versions which is such a sweet bonus. If you're into slice-of-life VN soundtracks that feel like a warm August evening in a small Japanese town, this is exactly that.