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I've never been able to time a flight around naps, but one "rule" that I have when I have options is that I want to be able to have bedtime at our destination. Obviously, it's not always possible, but if I can, I won't travel where it means overnight sleep is on a plane.

I would go with the morning. It will be crappy waking him up, but he'll be so tired that he will probably end up napping on the plane. If you leave at night, you're going to get into SD in the middle of the night. Then add on the time to get luggage, get the taxi/rental car, to the hotel, set up the crib, etc.

I had really a bad experience with late evening flights when LO1 was 10 months old, and don't want to do that again. I actually think it's easier going to the east coast because you get to sleep in. When you go to the west coast, they're still on east coast time, which is 3 hours ahead.

GOod luck!

I would do morning as well. With a transcontinental flight it's not long enough to get a full night's sleep and I know my LO wouldn't go back to sleep after getting off the plane, transiting to wherever you're staying, etc.

We have done a few Boston to LA/Palm Springs and we do the mornings. LO is typically in a better mood in the morning hours and will usually fall asleep on one of us. Good luck!!

I agree with everyone here, all my flights with J have been great except the one that was during bedtime. Morning flights have all been awesome!

We're doing morning flights this summer, too (4 y/o and 2 y/o from LAX to Dulles)! The earlier the better for all the reasons mentioned above.

Yeah, flying west to east is definitely tougher. (At least as adults and pre-baby.) I don't have any advice since we usually just take whatever non-stop flights available. Our kids are small so they would sleep after they ate every 5 ish hours. It worked for us last time we flew because it was 5-6 hour flight and we fed them at take off and landing and they mostly slept in between.