You don't have to transition the baby.  Once he's sick of it, he'll let you know.

With my kids, this usually happened on it's own.  As newborns, my children slept pretty soundly wrapped out. But after a while, they start to escape and wake themselves up. Then at this point, I find that they can't sleep without the wrap, but they keep escaping anyway. At some point I decide not to wrap them anymore, which is a transition period for babies. After a couple of nights when sleep becomes a struggle, they finally get used to not having it.

Good luck!

 I haven't had any experiance with this yet but have you tryed wrapping looser each night? Or try doing it for naps then move onto night sleep. I havent tryed any of this yet as my 1st daughter didnt need to be wrapped, but my new bub needs to be wraped a little so thsi is what i would try, will be good to see other tips :)