Transition dilemma

So when exactly am I supposed to start the transition of going to bed earlier, what with the school year looming...uh, I mean, hovering?

He is such a night hawk. Naptime seems to affect bedtime. Naptime used to be from 1ish to 3ish - sigh.... the good old days. Somewhere along the line he switched the naptime to 2ish...and if I try to wake him up at 4, 4ish, 4:30, 4:30ish...well. Let's just say that he is usually awake at 5. Ish.

Unless I bribe him with smarties or chips.

Either of which we now have in the house on a regular basis.



So back to the dilemma: how am I supposed to stick a kid to bed at 8 pm when:
1) it's still light out
2) he can hear lots of outdoor noises, like ice cream trucks driving by blaring music at 8:30 pm
3) he slept three hours at naptime, which he obviously still needs at 29 months?

Some days he won't nap at all. I'm sure I've complained blogged about this before somewhere along the line.

It has crossed my mind to keep him up at naptime for a few days in a row to move the night time bed time up a bit...but then I have to deal with crankiness and accidents and at least one minor crisis in the pre-supper-bedtime hours and that does not appeal to me at all.

So the plan, at least for now, is to wake him a little earlier each day, and hope he will go to have his nap a little earlier each day, until September.

I'm new at this, I have no idea if it'll work.