B.B.
I would call the provider and arrange a couple days that maybe he could go for an hour... Just so he can get used to the dropping off and momma always comes back idea.
I have myown inhome daycare and I can say its always worse when the parents dally... When you drop them off do it quickly and then scoot out the door. Always with a smile on your face and remain relaxed. Even if he's crying, GO!! With you out of sight then the provider can pull out her magic and calm him right down. :-) I have never had to call a parent because a child was not calming down... When you return make it light. I'm here... Quick hug... Not I MISSED YOU SOO MUCH!!! While you cling to him for dear life... That sends the wrong message... Give a quick hug and ask things like what did you do today? Wow, that sounds like FUN!! :-)
Since he is used to going to care its really not going to shock him about being dropped off... Just that its somewhere new... So try a quick visit without you there and he'll have no problems!