I pre-empt feeds/sleep by having a feed before we leave the house. DS is pretty easy to transfer to the sling or pusher when we get to where ever.
On school days we drop DD at 9, then go for a run, then play at the park. Lunch is around 12, then we have boob, and he will usually fall asleep, and wake before school pickup. If he doesnt then Ill put him in the pusher and go for a walk until he does fall asleep.