He is at the age where naps become difficult. I think you need to start a specific sleep schedule now that he is old enough that he can start learning to fall asleep on his own. It sounds strange but the earlier they go to bed, the longer they sleep at night. Have him wake up around 7 am, take a 9 am nap, a 1pm nap, possibly a 1/2 hour nap around 4pm and then bedtime at 7pm. If he wakes up early from his nap, let him stay in the crib until an hour is up. If he starts to really cry (not whine or babble), go in and check on him. My son often poops during naps and wakes himself up, but if that's not the problem, let him know that he has to rest for an hour by making him stay there. at night, it's still acceptable for him to wake up 1-2 times at night for a feeding. I exclusively breastfeed too so my son still wakes up once around 4 or 5 (he's 7 months). You can also get him a tiny security blanket (we found one about 12" x 12" that he loves to hug and chew on) or a little stuffed animal that you can include in his sleep routine and make sure you have a consistent sleep routine for naps and bedtime- bath & change(if needed), dim the lights in the house, read a story, breastfeed, rock or walk around with him for a few minutes, maybe sing the same song to him every night, and put him down with his security blanket/stuffed toy. And if he wakes up at night, be sure to keep the lights off as much as possible so he goes back to sleep easily and don't play with him or talk to him. Just get him changed, feed him, and put him back down. Otherwise he will think of it as playtime and wake up just to see you and play with you. I also suggest that you buy Healthy Sleep Habits Happy Child. Yes, this is one of the cry it out methods, but it also has lots of good advice and other methods that work well for people who don't believe in that. It explains how sleep works at different ages and why it is so important. We didn't do the strict cry-it-out method in the book. We never let him cry for more than 10 or 15 minutes, and if he started crying hard, we went in to comfort him. You also need to differentiate between whining & crying. Don't go in and pick him up the second he makes noise. Let him stay in there for at least 5 minutes and see if he falls back to sleep on his own. Luckily, it was much easier than we thought it would be. It only took about 3 nights before he fell asleep on his own without crying at all and those first nights he cried maybe 10 minutes at the most and it was never any hysterical crying. We were able to get our son to fall asleep on his own with minimal crying, and he stays asleep until 5 or so and then eats and goes back to sleep again. If we are staying over at someone else's house, he sometimes fusses before bed, but for the most part he does really well. And he started out as a newborn being a really difficult sleeper with some colicky behavior, so this does work even on those kids who are tougher. On nights that he does wake up, it is usually only when he has teething pain or something like that, and I feed him and he goes back to sleep easily on his own. If that is the case, a dose of Tylenol before bed should help him to sleep longer. Your son may be getting his second tooth. My son got his first two within two weeks.