THE BOXES WERE HIDDEN DESIRES things that Chariot has wanted to do/enjoyed doing with Viola, but is too derpy to actually get around to asking her if she wants to do them. The gloves were asking her to train him/spar with him in hand-to-hand (I SWEAR HE HEARD SHE COULD FROM SOMEWHERE BUT I CAN'T REMEMBER WHERE), the shoes were from having fun at that dance, etc. By leaving them out, he's more willing to approach her about these things!

Candyland is dumb Chariot symbolism for ADVENTURES. Like, how he's done an adventure quest with Yuri (that ended in failed success), he wants to do one with Viola that is... not as dangerous. Thus candyland :B