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I have to give D an early nap every once in awhile. I guess I'd suggest slowly pushing the one nap back. So when he starts to get tired, wait another 15 minutes or so. One nap around noon seems to be the most common. We started with naps around 11 and eventually it's 12 or 12:30.

Do walks help him sleep? Maybe you can do a long walk in place of the afternoon nap so he's resting?

@hilsy85: Ah...I can't imagine dealing with the weather! I'm sure that's part of the problem too. Maybe try a bath or other bedtime like activity before the nap to start it later and maybe trick him into sleeping longer?

Aww...I was hoping this would go smoothly for you!

How long is he sleeping at night?

A 1.5hr isn't bad...it just really sucks if it starts before noon and he refuses to take a 2nd nap. My LO often took 1h15 naps at the beginning of the transition (and truthfully, we never got consistent magical unicorn 3-hr naps either).

You could either try the mini-catnap in the mid-morning or just keep him busy and constantly entertained so he catches a 2nd wind. Ideally he would have a minimum of 5 hours before his nap then 5 hours after.

Hmm...I'm sure the illness plays a part. Eventually things will even out. We actually transitioned then traveled a week later. We went 2 time zones west and dealt with EWUs and short naps while also staying in a hotel room and house hunting. It will get better!! After a few days his nights got much longer (12-13) and naps were only 1-1.5...sometimes 2+ though. I think it's a misconception that the 2 naps will consolidate into one giant nap. I do think night and nap sleep distribution constantly fluctuates.

My best advice would be to minimize overtiredness and do early bedtimes for now (and maybe deal with slightly early wake ups) until he can handle a longer waketime in the morning so his nap falls midday. Good luck!

We had the same issue! DD showed signs around 18 months but at last we went back to 2 naps because she just wasn't getting enough rest. She showed signs again at 22 months (super late) and transition went much smoother. It took less than a week to get to the new schedule once she was really ready.