I think I would work towards getting him to 1 day sleep & sleeping in later then 5am! I would try & darken his room as much as possible so in the mornings there isn't anything that may wake him so early. Drag out that early morning nap as long as you can, work towards 10 am for a few days then 10.30 & so on. I think at this age a nap around 11 am or just after he has had lunch for at least 2 hours would be much better then a 5 am start with two sleeps in the day. Having just the one sleep would also help work towards an earlier bed time (if thats what you want). Hopefully with just the one day sleep he will slot into a nice bed time & wake up at a more suitable hour of the morning, say 8am! LOL I get up at 7.30 during the week & often have to wake Isla just before 9am so I can get Evan to school.

I have no suggestion on how to *get* him to sleep when he is playing as I have always fed to sleep. I really struggle with sleep times if for some reason they are refusing the breast, Its something i hope to change a little this time round. I am more then happy to feed to sleep, but I would like to be able to out them down for a sleep & just walk away & know they will go to sleep with out me if its needed. At the moment, I can't leave Isla (it was the same with the boys) to go out at night because DH wont be able to get her to sleep. The only thing I do that runs into bed time is the P&C meetings & I still leave before they finish so I can get back by 9 at the latest.

Anyway, I am with the others to just keep doing what works & what your comfortable with as far as lettin ghim cry, but usually I think at this age they just get too worked up if you leave them for to long, the other thing that maybe you could try if you wanted too is lay with him in your bed for day sleeps, that way you get a nice rest up too.