I think this’s interesting topic ! thank all for writing this.

At this point he will be especially clingy while you are there for the first day or two, but if you tell him you will stay and don’t even go to the restroom without telling him first, he should start to feel more comfortable about checking things out. You can help with this by engaging in the different activities silently. Eventually, he should become interested in the activities as well. Once he does, don’t say a word. Just continue to play next to him. After a day or two of him enjoying himself without needing to be by your side and hopefully not even looking for you, prepare him that the next day you will leave after snack but then be back to pick him up. Gradually work yourself out at the pace he needs. You are his safety. He can’t enjoy himself if he does not feel safe. But with you there, he can build confidence in the safety of that space and those people. Slowly, as he becomes more secure, he will not need you there to feel safe and have a good time.

Make sure the workers do not take away his hat or teddy. That is like me taking your car keys or bus fare.

I know my ideas will probably not be your first choice. However, I think for the long run, this is what I would do. I have been a nanny for years and worked at childcare centers with many types of kids. If you follow through with this and show him in your actions that you respect his feelings by being honest (not sneaking out), moving at his pace, and letting him find his security in what works for him (you and then his teddy and hat), I think you will find yourself no longer than a few weeks from now with glorious hours to yourself and a happy little boy that loves his nursery school.