DD just started K. We live at the edge of the walk zone, so no handy school bus... She's out at 2:30, and our walk is 20ish minutes (I'm slow getting the double stroller up the hill.) We have to leave around 2pm to get drinks, snacks, shoes, toys, etc for the 1 hour (round trip) in the stroller. Besides the fact that an hour isn't long enough for his nap (usually sleeps 1:30-4 or longer)
On Monday, DS1 (3.5) fell asleep in the stroller, but DS2 (26 mos) did not sleep a wink. He slept when we got home (3ish) until DH woke him up for dinner at 5pm. Yesterday, we were doing errands, so we picked her up in the car. Lots of time waiting in line, etc. and he waited until we were home to sleep. Again, he slept 3ish-5, but this time when he woke up he was hysterical.
Today I fed the boys lunch at 11:45 and put him down at 12:00. He is quiet, so I'm assuming he'll sleep 12-2. Do you think this is the best time to let the toddler nap with this mid-nap mandatory pickup time? I wish there was a good carpool option, but then again I like meeting the other parents, seeing the classmates, saying hi to my old coworker/teacher friends, etc.
If you have a napper and a school-age kid, how do you make it work? Is there ANY way to make him sleep in the stroller? I tried reclining the seat and covering him with the shade, but it didn't work.

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