Starting William's Bedtime Routine

This week I have more or less 'finalized' William's daytime sleep schedule and bedtime routine. I feel like what I've come up with is really great and will be work well with William's natural schedule but the last two days of the routine have been a bit rough.

His Natural Routine

On his own, William will wake up for the day around eight or so and I'll nurse him while I eat breakfast. Afterwards he will either fall back asleep for another hour or so or be wide awake and play on his activity mat for awhile and be silly and work on spacial orientation and work on building his muscles. He then usually falls asleep around 1pm after a feeding and will sleep for at least an hour and then want to play again afterwards. He usually takes a catnap right before or right after Seth and I have dinner then play again (surprise, surprise he's a little monkey). Then William will eat and take a catnap around 7 or so. By 9pm he is ready for the last big feeding before bed


 he doesn't go to sleep afterwards. William likes to stay up until

at least

 11pm but it's usually closer to midnight when he finally falls asleep. He then just wakes up once at night usually somewhere between 3 and 4am.

The New Routine

Going off of his natural routine, I've sort of come up with a sleep schedule that I think will be ideal for the whole family if we're able to stick to it.

7:30am Wake Up -

change his diaper + clothes, nurse + burp him

Active Playtime

Morning Nap -

 sometime between a second feeding and his lunch feeding

More Playtime

1:00pm Feeding

 - this is essentially William's lunch time

1:30pm Afternoon nap -

I'd like to keep this time pretty strict for a nap but if he falls asleep at noon instead, we'll make it work. This nap he usually sleeps for at least an hour sometimes close to two hours.

Evening Nap -

this usually happens sometime between 5 and 7.

8:00pm Start Bedtime Routine -

 change his clothes + diaper and then nurse and burp him followed by story time and cuddles and then a quick snack before going to bed. Ideally, this would all be done by 9:30pm.

This routine will be wonderful for our family once William starts sticking to it. But the last few days of starting it have been seriously rough. The other night he refused to sleep until midnight and then woke up hungry at 2am and it took me an hour to get him to sleep only for him to wake up hungry at 4am. Not awesome. That made the next day of following the routine, nearly impossible because he was so tired. He was absolutely miserable which made for a long day for us and even though I was able to keep him awake as needed, he still refused to go to sleep before midnight. I'm hopeful that we'll be able to nail down the routine and get him to bed before 11 (seriously, I would settle for 10:30!) but it's also hard not to get frustrated and feel defeated. Do you experienced mamas have any tips for nailing down a sleep routine? Any thoughts on the routine I've come up with? Any help is much appreciated!