Tonight works best because Disneyland slows down in a good way after dark. If you want a couple of headliners, use the lighter evening lines first, then walk through Fantasyland at dusk for photos, when the soft light brings out details you miss in daytime. Keep an eye on the app for the Disney Illuminations time, and if it is around 23:00 in summer, aim to be on Main Street or in Central Plaza by about 22:30 so you can stand together without splitting up. One thing people forget is that some Main Street vehicles can pause around parade or crowd peaks, so it helps not to leave them for the very end. Then, when the show ends and the crowd starts moving, you can step right back into the night and head out together.
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