What temperament is your little one?
My lo is spirited/touchy. For our wind down ritual, I put him in his crib, I sing him some songs then, he inevitably starts whining. If it progresses to crying, I pick him up and sing him a couple more songs or just hold him. Sometimes it's PU/PD.
I's not a very good wind down ritual for him but, honestly, I have yet to find a very good one that works (and I've tried a few). He just seems to go from okay to overtired within minutes. Also, he doesn't sit still long enough for me to do something relaxing with him. If I sit down with him, he wants to climb the back of the chair or play with the crib (which is next to the chair), or he starts whining/crying (which I know is a touchy/spirited trait). All I can say is SHEESH!