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R was also home with me and then with our nanny until 21 months. We started him 3 days a week 830-330 (Montessori program) and still with the nanny one day and she also did their after care. I hate to say but we had a really tough transition. He cried a lot, had a tough time with the transition from activity to the next, barely ate at school, and barely played. I think it would have resolved sooner but he got quite sick after the first week and missed several days of school. It took a month for him to get more into the program, but continued to cry a lot at drop offs and during activity transitions. It honestly broke my heart a little and I almost totally pulled him, but his teachers encouraged us to keep at it and my husband really wanted to forge ahead. Just at the two month mark, due to unforeseen circumstances, we separated from our nanny. I added a fourth day to his schedule (he is home with me one day) and added late care from 330-530 for both he and his brother. I then saw a dramatic change in his demeanor surrounding school. He started skipping off to school in the morning, loves his buddies, never cries there, and is happy as can be. I'm not sure if 2 months was the magic number for us, or adding a day, or simply just having total continuity of care....but it's great and I'm so happy we persisted. A key was being really open with his teachers -- and following up with them a loT. Our story is definitely not typical, but I wanted to share it so that you know that even if you have a rough start, it can turn out to be great!

My suggestions would be to send him half days the first few days but then have him go full days. Make his drop offs very matter of fact and not drawn out - it's time for school now, I love you and I'll be back to get you at 5. Bye!! No tears or clinging to him etc. Ask the teachers to help him separate from you. Also talk to him about it a lot in advance. He is young but will understand more than you think. Read a few books about it! I like I love you all day long a lot!

Great advice here. My girl started daycare at 8 weeks but had a really hard transition from one class to the next at 18 months. She cried at dropoff for about 6 weeks. She was mostly okay after drop unless she saw her prior teacher. The teacher tried hard to be out of sight but they have to cover each other. She's over two now and will still get upset at drop if the routine is different. Keep goodbyes brief and let the teachers help.

@fuzzypeaches: our providers told us he was on the severe end in terms of transitioning. I think most kids who have never been to school fully transition after a month.

DS started playschool at 23 months, right when he was in the midst of an insane clingy phase. He only goes 2x a week, so it did take a few weeks for him to get acclimated (would cry at dropoff, I would feel terrible, but it would only be like 5 mins total), and now he is totally fine with my leaving. I think the more he goes, the better it gets. When he is off for holidays or school is closed and he only goes 1x a week, that's when it gets difficult again. Good luck!