Hi there. My daughter gave up her morning nap right around her one-year birthday. She was always solid in the morning but afternoons were always challenging and sometimes short, so I figured we'd give the one nap thing a try. After the transition she started sleeping much longer in the afternoon, usually at least 2 hours. One intermediate step to try would be waking him up from his morning nap after an hour, no more than an hour and a half. If he still seems awake in the afternoon, I would experiment with dropping to one nap. The trick is to gradually move the one nap later and later in the day, because he may still want to go back to sleep at 9am. So over the course of a week or two, keep him up til 10, then 10:30, then 11:00, until you can get the nap to move until mid-day. During this period you should put him to bed extra early, to help him adjust and still get his sleep needs met. When you drop to one nap I would definitely put him to bed by 6:30 or 7 at the latest. These are not all my ideas, I learned everything I know from "Healthy Sleep Habits, Happy Child," by Dr. Weissbluth. It's a good resource, especially since it sounds like he has been a challenging sleeper all the way around. Good luck.