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Is there a way to move his nap earlier in the day? I'm no expert for sure but my DD is only 19 months and 3 is just too late for her to be sleeping. I usually put her down between 11-2, but she really only naps for 1.5 hours max. I'm lucky if she sleeps 12-1.

But my DD also has an earlier bedtime (7pm) so idk of my advice is helpful.

We got a baby monitor where you can talk through the camera to the baby, and when I see my DD out of her bed and playing I'll tell her to go back to bed and lay down through the monitor. So far it's worked, and she listens, which is almost comically absurd to me because she is in a huge toddler defiant stage and never listens to me otherwise.

Sorry you're going through this! We also recently transitioned to a toddler bed and it's been okay but naptime is about half of what it was, and she frequently gets hysterical when she wakes up. When she was in a crib she'd just sit in there and play. But now she lays at the door and cries for us when she wakes up.

@macintosh: I'm going to be the dissenter and say that it sounds like it could be overtired and wired.
My son is 2.5 (last week) and his schedule is:
7:30ish awake for the day
12:30/1pm - 3pm nap
7/7:30pm bedtime

He truly can't handle a lot of wake time in the 2nd half of the day otherwise he's really difficult to get down. He's still in a crib but if we deviate from a 7/7:30 bedtime (4 hours from nap wake up) he will kinda freak about his bath, only wants me (even though daddy does bedtime practically every night), won't let us put on PJs, etc etc. He just becomes difficult.
So I would suggest an earlier bedtime. Start with 7:30 for a week and see how he does. A half hour truly can make a difference (it does for us).

@macintosh: Yea that could be true too! How long has this difficulty winding down been going on? A lot of sleep consultants say that you shouldn't make any permanent adjustments for a while to ensure that it's not just a phase and that it actually does need permanent solution. I forget what it is exactly - maybe more than a month?

I don't see a problem with your schedule - B is 3 and is just starting to drop his nap but he's always slept 12:30/1ish to 2:30 or 3 with no problems, and goes to bed at 7:30, although he's up earlier, at 6. Fingers crossed that it's just a phase!

It can take my DD (23 months) about an hr to fall asleep. She usually just roams around the crib reading, throwing toys and taking her pjs off. No advice just commiseration. She's been like this for a few months but I think the daylight savings change has made getting to sleep harder for her... she's now sleeping in in the mornings!

We're at a similar point with DD, who is now transitioning to a floor bed from her crib. We are doing a sleep-training type of approach to bedtime, though - go through the entire bedtime routine like normal, then lights off and shut the door. She cries for 10 minutes and then puts herself to bed.

It does really sound to me like your LO needs an earlier bedtime. Falling asleep at 9pm is VERY late for a kiddo this young! We put DD to bed at 7:15 and she's asleep by 7:40 at the latest, sleeps straight through til morning, and naps 1.5-2 hours at daycare.

I'd actually say he's overtired! My 3 year old will nap 3-530 and still go to bed at 830!

@PawPrints: ha! Hopefully the novelty will wear off. We had it for years and never used it. Then we brought it into bed out of desperation when we weaned from the paci and he definitely played with it for a couple days turning on the different colour lights, but now he doesn't touch it. I was just happy he wasn't screaming while he played with it and eventually he fell asleep! He's in a crib still so we turn it on when we turn out the lights, read books, then it stays at the end of the crib and he has his other loveys up top with him.

If that doesn't happen, maybe it could be put in a place out of reach/explain that she can't touch it at night because it's 'special'?

Can you try this clock:

My Tot Clock (New & Improved) https://www.amazon.com/dp/B00NC10YFA/ref=cm_sw_r_cp_api_32xYybMT3C6V9

It has different color faces for different times like nap or night or wake up or whatever - like 5 colors - so you can use it as a prompt. Like bedtime routine can be yellow but as soon as the lights are blue it's night night time.

We use a low tech version with a digital kitchen timer to help our son transition. We use a 2 minute warning and say "okay when the alarm goes off it's time to get out of the tub" or whatever.

Definitely would try an earlier bedtime. My LO is 2 and we have had the same routine for a long time - PJs, teeth, books, songs all start at 6:30 with hope to sleep by 7, but never past 7:30. When we first started her in the open crib (at 21 mo) we went back to the Ferbet method (checks after 3,5,7 mins) and it took 3 nights before she would just put herself to sleep. We started potty training at 22 months and have had some set backs (requires more patience if she is asking to go potty) but overall she still gets it. We just gave her the usual lovies - no special toys - the new bed seemed special enough!