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When we had to do a cross country drive we did a day drive and I pumped and bottle fed from my seat next to the baby. We stopped every two to three hours for a diaper and tummy time break. But we had a newborn. I would still pick daytime with a four month old though.

We took a road trip when E was 7 weeks and other long distance travel at 6, 8, 10, 21.5 months. We almost always day drive. I cannot stay awake at night to help keep my husband awake for nighttime driving. For the 7 week trip I sat in the backseat with E the whole time. We bought an converter for my pump and then I bottle fed so that feeding didn't take up too much time. We as adults would take breaks every 2-3 hours and always made sure to get E out of her carseat. For the later trips I tend to sit up front for most of the drive and move to the back as needed for short periods (I have totally switched seats on the side of a highway when absolutely necessary). As she gets older E does better if I am not sitting next to her the whole time but that obviously is baby specific. I will forever and a day pick not during my personal sleeping hours, so even on trips where we get a head start at night after work we stop by about 9pm and stay at a hotel and then get up the next morning and continue on. Pack way more wipes then you think you will need so when your baby has a massive blowout and starts playing with her own poop and you are 20 miles from a rest stop you can essentially bathe her in wipes when you can finally stop.

We once embarked on a 4 hour drive with our baby at about the same age. He fell asleep about 20 minutes in, and slept the whole way. My husband kept whining that he was hungry and had to pee and I wouldn’t let him stop in case the change woke the baby up.

All that to say that I’d probably leave at around morning nap time, hope the lull of the car got you an extra long nap, and then go from there.

We've never done a trip that length, but I would probably choose night. However, it's mostly because my LO gets carsick if he has any toys, books, etc in the car - since he can't have anything to play with he requires non stop entertainment from me instead and generally hates it but will sleep well if he's tired. If I had a smaller baby that would sleep a lot during the day or a kid that could be entertained, I would definitely do daytime....

Day trip for sure. Most of our trips are 12 hours long. We actually start early in the morning so that the kids are still tired enough the car ride lulls them back asleep. At that age, you want to optimize the time they spend asleep. So by the time they wake up from their first 'nap', you are ready for a break and you can do a feeding stop.

On past trips around that age, I would pump in the front seat and then climb into the backseat to feed the baby. When it was clear they were getting tired, I'd swap back up to the front because my kids refuse to sleep if they can see you.

Have junk toys that make sound just for the trip that you parcel out as needed. Use blankets and stuffed animals to play peekaboo and tug of war, etc.