advise and reassue me please ... road trip with a toddler

Of course 2 months ago, I thought sure, no problem... DS is so easygoing as of late, and is so interested in looking at the window when we drive ...

Next week, we are doing it, and I'm freaking out. We are driving up to Toronto. And I'm thinking no way he'll be happy looking out that window more than 1 hour.

Would you drive through the night? Or just start driving at 3am? Or just leave the next morning/afternoon and find ways to occupy LO.

I'm so worried that if we drive through the night, even if we take turns one of us will fall asleep at the wheel. Neither of us had driven middle of the night like this for quite some time. I'm notorious for getting sleepy driving even when I'm fully rested.

What would you do? DS is 19m and generally very patient and well behaved.

Do we plan stops along the way? Or just stop where ever, do stretch/eat?