Need Advice for 2 1/2 Year Old That Doesn't Sleep Well

Hi J.,
There could be a couple of reasons that he is doing this. Has he always gone to bed late? Has he had a good bedtime routine in the past? If he hasn't you may want to start one. Both of my kids have a bedtime routine that may take up to a half an hour.
You also need to either make the nap earlier or eliminate it. My first son stopped taking naps around that time. He would want to take a nap late but I would entertain him until dinner (6ish) and then give him a bath and put him to bed. Sometimes as earlier as 6:30-7:00. He slept through the night without waking. Some days were harder than others to keep him up and it took probably a good 6 months until he adjusted. I would try and keep him up for an hour or two and then put him to bed. Good luck.
Chris

Don't ever let him nap at 5:30. If my kids slept from 5:30 to 8, they'd be up till 11 also. Make sure his nap is much earler in the afternoon, like right after lunch. Even if he sleeps from 1-3 he'd probably be ready for bed by 8ish.

You really need to adjust his schedule, my 3 1/2 year old was EXACTLY the same way, I had to get rid of naps ..period. which is really hard when they are tired at night, it required a lot of entertaining in the evening, and then around 6:30 we start getting ready for bed, it took about a week, and at times I wanted to pull my hair out, but it is possible so long as you put your mind to it, and stick with it, have meals prepared ahead of time so that is one less added stress at night that you have to worry about. I have new issues w/ her know but for the most part she is pretty easy to get to sleep at night, but that is only if she hasn't had a nap or fallen asleep in the car, Good luck, it will get better if you put a little effort into changing his routine.

Have you tried giving him a bath with sleepy time bath, then using lavender lotion? My last child was the same way, and I would rock him about a half hour before his bed time and scratch his back real light, he still calls it "scratch my back like it tickles" it always worked on him to calm him down and transition into sleep time. Good luck!

J.,
Well, you can try to limit the nap time and only allow an hour then wake him... Have activities ready to keep him awake...
Also, tough love, let him cry it out...this wont happen overnight by any means.... took me two weeks with my oldest (now almost 18 and cant sleep enough lol)
Each night gets easier on you and him....
Good Luck
T.