When DD was five months old she would have three naps each day.
1: 8.30am-9am
2: 11.30am-12pm
3: 2.30pm-3pm
I just wanted to clarify this from my last post, sorry if it didn't make sense - the above times are when she went down for the naps, not the start and end time of her naps! So she would go down between 8.30am and 9am for her nap. Sorry bout that.

Mummaloo, sometimes DD won't re-settle either, such a pain but theres nothing else you can do. I think giving him the wind down time before every nap like the sling is a great idea, lets him know whats coming up.

Do you get him up at 5.30am? Maybe you could try leaving him in his cot an extra 10-15 minutes each day until 6.30am or whenever you want to get up?

DD is also more tired in the morning and often went back down at 8am for a nap at 5 mths old.